# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_2024jrh0012_auto_res
_database_code_depnum_ccdc_archive 'CCDC 2388584'
loop_
_audit_author_name
_audit_author_address
'Jennifer Hiscock'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H15 N2 O6, H2 O, C16 H36 N'
_chemical_formula_sum            'C29 H53 N3 O7'
_chemical_formula_weight         555.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2F3
_chemical_oxdiff_usercomment     '150 K lisa W 3-34-3'
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'

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

_cell_length_a                   8.6519(3)
_cell_length_b                   9.5272(3)
_cell_length_c                   19.0975(7)
_cell_angle_alpha                93.880(3)
_cell_angle_beta                 95.670(3)
_cell_angle_gamma                100.995(3)
_cell_volume                     1531.68(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5988
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.7690
_cell_measurement_theta_min      4.6400
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 0 0.1323
1 -5 0 0.1323
5 0 4 0.0519
-5 0 -4 0.0519
-1 0 5 0.0064
1 0 -5 0.0064

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9994 4.9970 -0.0046 -0.0921 -0.2257 0.7725
0.9994 -4.9970 0.0046 0.0921 0.2257 -0.7725
5.0045 -0.0005 3.9954 -0.2168 -0.9339 -0.2985
-5.0045 0.0005 -3.9954 0.2168 0.9339 0.2985
-0.9994 -0.0018 5.0007 -0.4163 0.0926 0.0088
0.9994 0.0018 -5.0007 0.4163 -0.0926 -0.0088

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10263
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.672
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  25.00   1.00    4.00    --  -41.91  57.00-150.00   88
  2  ω    -86.00 -57.00   1.00    4.00    --  -41.91 125.00 -90.00   29
  3  ω    -65.00  31.00   1.00    4.00    --  -41.91  38.00   0.00   96
  4  ω   -114.00 -16.00   1.00    4.00    --  -41.91 -57.00  60.00   98
  5  ω     77.00 175.00   1.00   15.99    --  103.72  30.00   0.00   98
  6  ω     88.00 113.00   1.00   15.99    --  103.72-125.00 -30.00   25
  7  ω     79.00 173.00   1.00   15.99    --  103.72  30.00 -90.00   94
  8  ω     50.00 133.00   1.00   15.99    --  103.72 -61.00-180.00   83
  9  ω     71.00  97.00   1.00   15.99    --  103.72 -94.00-180.00   26
 10  ω     45.00 123.00   1.00   15.99    --  103.72 -30.00 -60.00   78
 11  ω     98.00 132.00   1.00   15.99    --  103.72 125.00 -90.00   34
 12  ω    134.00 175.00   1.00   15.99    --  103.72 125.00 -90.00   41
 13  ω     28.00  60.00   1.00   15.99    --  103.72 -94.00-150.00   32
 14  ω     88.00 113.00   1.00   15.99    --  103.72-125.00 120.00   25
 15  ω     40.00  72.00   1.00   15.99    --  103.72-125.00 120.00   32
 16  ω     41.00 110.00   1.00   15.99    --  103.72-125.00 150.00   69
 17  ω     28.00  54.00   1.00   15.99    --  103.72 -94.00-180.00   26
 18  ω     81.00 106.00   1.00   15.99    --  103.72 -94.00-150.00   25
 19  ω     28.00 133.00   1.00   15.99    --  103.72 -77.00 -60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0199682000
_diffrn_orient_matrix_UB_12      -0.0145090000
_diffrn_orient_matrix_UB_13      -0.0792724000
_diffrn_orient_matrix_UB_21      -0.1736729000
_diffrn_orient_matrix_UB_22      -0.0799266000
_diffrn_orient_matrix_UB_23      -0.0162289000
_diffrn_orient_matrix_UB_31      -0.0526761000
_diffrn_orient_matrix_UB_32      0.1440489000
_diffrn_orient_matrix_UB_33      -0.0087151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4603
_reflns_number_total             5412
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.3949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C29A-C28 \\sim C29B-C28 \\sim C17-C16 \\sim C21-C20 \\sim C25-C24
 with sigma of 0.02
3. Others
 Sof(H28C)=Sof(H28D)=Sof(C29B)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H28A)=Sof(H28B)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
4.a Free rotating group:
 O7(H7A,H7B)
4.b Ternary CH refined with riding coordinates:
 C9(H9)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B), C11(H11A,H11B), C18(H18A,H18B), C26(H26A,
 H26B), C12(H12A,H12B), C23(H23A,H23B), C15(H15A,H15B), C24(H24A,H24B),
 C19(H19A,H19B), C16(H16A,H16B), C27(H27A,H27B), C20(H20A,H20B), C28(H28A,H28B),
  C28(H28C,H28D)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C7(H7), C4(H4), C3(H3A)
4.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C), C29A(H29A,H29B,H29C), C29B(H29D,H29E,H29F)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.11049(12) 0.63167(10) 0.34073(5) 0.0266(2) Uani 1 1 d . . . . .
O2 O 0.19121(13) 0.82539(11) 0.73845(5) 0.0287(2) Uani 1 1 d . . . . .
O3 O -0.05644(12) 0.62323(11) 0.62214(6) 0.0276(2) Uani 1 1 d . . . . .
H3 H -0.0800 0.5372 0.6312 0.041 Uiso 1 1 calc R U . . .
O4 O 0.17618(13) 0.56454(11) 0.60511(6) 0.0322(3) Uani 1 1 d . . . . .
O6 O 0.03088(17) 0.83374(12) 0.36903(6) 0.0409(3) Uani 1 1 d . . . . .
O7 O -0.01846(15) 0.44489(13) 0.21268(6) 0.0378(3) Uani 1 1 d G . . . .
H7A H 0.0079 0.5074 0.2494 0.057 Uiso 1 1 d G U . . .
H7B H -0.0612 0.3660 0.2296 0.057 Uiso 1 1 d G U . . .
O1 O 0.14480(15) 1.21491(14) 1.02985(6) 0.0433(3) Uani 1 1 d . . . . .
N2 N 0.09918(16) 0.91112(13) 0.63767(6) 0.0272(3) Uani 1 1 d . . . . .
H2 H 0.0474 0.9731 0.6190 0.033 Uiso 1 1 calc R U . . .
N3 N 0.51023(14) 0.45866(12) 0.75031(6) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.08765(15) 1.03151(13) 0.74332(6) 0.0267(3) Uani 1 1 d . . . . .
H1 H 0.0446 1.0878 0.7160 0.032 Uiso 1 1 calc R U . . .
C8 C 0.13007(17) 0.91662(15) 0.70911(8) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.10332(16) 1.07225(15) 0.81610(8) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.08603(16) 0.72861(15) 0.38510(7) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.09187(18) 0.65247(15) 0.60855(7) 0.0238(3) Uani 1 1 d . . . . .
C6 C 0.06789(17) 1.20457(16) 0.83574(8) 0.0257(3) Uani 1 1 d . . . . .
H6 H 0.0357 1.2614 0.8002 0.031 Uiso 1 1 calc R U . . .
C9 C 0.14952(17) 0.80581(15) 0.59163(7) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.2680 0.8257 0.5968 0.029 Uiso 1 1 calc R U . . .
C14 C 0.62292(17) 0.58800(15) 0.72952(8) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.6938 0.6335 0.7722 0.029 Uiso 1 1 calc R U . . .
H14B H 0.6900 0.5535 0.6957 0.029 Uiso 1 1 calc R U . . .
C22 C 0.61417(16) 0.36226(15) 0.78219(8) 0.0239(3) Uani 1 1 d . . . . .
H22A H 0.6870 0.4189 0.8218 0.029 Uiso 1 1 calc R U . . .
H22B H 0.6800 0.3350 0.7460 0.029 Uiso 1 1 calc R U . . .
C11 C 0.09040(18) 0.82262(15) 0.51476(7) 0.0243(3) Uani 1 1 d . . . . .
H11A H -0.0262 0.8133 0.5101 0.029 Uiso 1 1 calc R U . . .
H11B H 0.1371 0.9201 0.5029 0.029 Uiso 1 1 calc R U . . .
C2 C 0.12702(18) 1.17425(18) 0.95849(8) 0.0311(3) Uani 1 1 d . . . . .
C18 C 0.40348(17) 0.50391(16) 0.80232(8) 0.0283(3) Uani 1 1 d . . . . .
H18A H 0.3359 0.5635 0.7785 0.034 Uiso 1 1 calc R U . . .
H18B H 0.3325 0.4166 0.8144 0.034 Uiso 1 1 calc R U . . .
C26 C 0.40079(17) 0.38113(16) 0.68655(8) 0.0276(3) Uani 1 1 d . . . . .
H26A H 0.3241 0.3028 0.7030 0.033 Uiso 1 1 calc R U . . .
H26B H 0.3397 0.4494 0.6661 0.033 Uiso 1 1 calc R U . . .
C12 C 0.13235(19) 0.71258(16) 0.46242(8) 0.0286(3) Uani 1 1 d . . . . .
H12A H 0.2483 0.7179 0.4698 0.034 Uiso 1 1 calc R U . . .
H12B H 0.0804 0.6158 0.4732 0.034 Uiso 1 1 calc R U . . .
C23 C 0.52909(18) 0.22575(16) 0.80950(9) 0.0286(3) Uani 1 1 d . . . . .
H23A H 0.4535 0.1677 0.7712 0.034 Uiso 1 1 calc R U . . .
H23B H 0.4690 0.2499 0.8486 0.034 Uiso 1 1 calc R U . . .
C15 C 0.54595(18) 0.70194(15) 0.69663(8) 0.0280(3) Uani 1 1 d . . . . .
H15A H 0.4668 0.7284 0.7265 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4906 0.6640 0.6493 0.034 Uiso 1 1 calc R U . . .
C7 C 0.07860(18) 1.25547(17) 0.90629(8) 0.0300(3) Uani 1 1 d . . . . .
H7 H 0.0528 1.3458 0.9187 0.036 Uiso 1 1 calc R U . . .
C24 C 0.65298(19) 0.14067(17) 0.83570(9) 0.0327(4) Uani 1 1 d D . . . .
H24A H 0.7130 0.1186 0.7962 0.039 Uiso 1 1 calc R U . . .
H24B H 0.7288 0.2008 0.8732 0.039 Uiso 1 1 calc R U . . .
C19 C 0.48654(19) 0.58691(16) 0.87030(9) 0.0319(3) Uani 1 1 d . . . . .
H19A H 0.5576 0.6753 0.8595 0.038 Uiso 1 1 calc R U . . .
H19B H 0.5518 0.5278 0.8960 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6730(2) 0.83389(17) 0.69016(10) 0.0343(4) Uani 1 1 d D . . . .
H16A H 0.7298 0.8695 0.7375 0.041 Uiso 1 1 calc R U . . .
H16B H 0.7510 0.8069 0.6598 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1513(2) 0.99055(17) 0.86908(8) 0.0314(3) Uani 1 1 d . . . . .
H4 H 0.1760 0.8997 0.8569 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1629(2) 1.04189(19) 0.93932(9) 0.0351(4) Uani 1 1 d . . . . .
H3A H 0.1960 0.9857 0.9750 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4803(2) 0.3178(2) 0.62867(9) 0.0389(4) Uani 1 1 d . . . . .
H27A H 0.5323 0.2413 0.6467 0.047 Uiso 1 1 calc R U . . .
H27B H 0.5628 0.3932 0.6136 0.047 Uiso 1 1 calc R U . . .
C25 C 0.5806(2) 0.00123(18) 0.86462(10) 0.0411(4) Uani 1 1 d D . . . .
H25A H 0.5054 -0.0589 0.8277 0.062 Uiso 1 1 calc R U . . .
H25B H 0.5250 0.0226 0.9051 0.062 Uiso 1 1 calc R U . . .
H25C H 0.6647 -0.0498 0.8796 0.062 Uiso 1 1 calc R U . . .
C20 C 0.3647(2) 0.6262(2) 0.91614(11) 0.0466(5) Uani 1 1 d D . . . .
H20A H 0.3009 0.6857 0.8899 0.056 Uiso 1 1 calc R U . . .
H20B H 0.2922 0.5371 0.9250 0.056 Uiso 1 1 calc R U . . .
C1 C 0.0809(2) 1.3349(2) 1.05176(10) 0.0500(5) Uani 1 1 d . . . . .
H1A H -0.0299 1.3211 1.0312 0.075 Uiso 1 1 calc R U . . .
H1B H 0.1420 1.4220 1.0358 0.075 Uiso 1 1 calc R U . . .
H1C H 0.0862 1.3444 1.1034 0.075 Uiso 1 1 calc R U . . .
C21 C 0.4358(3) 0.7066(2) 0.98596(10) 0.0484(5) Uani 1 1 d D . . . .
H21A H 0.5020 0.7983 0.9778 0.073 Uiso 1 1 calc R U . . .
H21B H 0.5009 0.6493 1.0120 0.073 Uiso 1 1 calc R U . . .
H21C H 0.3508 0.7245 1.0136 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6014(3) 0.9530(2) 0.65869(14) 0.0589(6) Uani 1 1 d D . . . .
H17A H 0.5590 0.9230 0.6093 0.088 Uiso 1 1 calc R U . . .
H17B H 0.6834 1.0402 0.6610 0.088 Uiso 1 1 calc R U . . .
H17C H 0.5157 0.9722 0.6855 0.088 Uiso 1 1 calc R U . . .
C28 C 0.3588(3) 0.2558(2) 0.56600(12) 0.0610(6) Uani 1 1 d D . . . .
H28A H 0.2799 0.1804 0.5832 0.073 Uiso 0.554(5) 1 calc R U P A 1
H28B H 0.3026 0.3331 0.5528 0.073 Uiso 0.554(5) 1 calc R U P A 1
H28C H 0.2502 0.2414 0.5801 0.073 Uiso 0.446(5) 1 calc R U P A 2
H28D H 0.3780 0.1625 0.5465 0.073 Uiso 0.446(5) 1 calc R U P A 2
C29A C 0.4002(4) 0.1991(4) 0.50638(17) 0.0429(9) Uani 0.554(5) 1 d D . P A 1
H29A H 0.4626 0.2750 0.4828 0.064 Uiso 0.554(5) 1 calc R U P A 1
H29B H 0.3045 0.1537 0.4750 0.064 Uiso 0.554(5) 1 calc R U P A 1
H29C H 0.4637 0.1270 0.5176 0.064 Uiso 0.554(5) 1 calc R U P A 1
C29B C 0.3806(5) 0.3691(5) 0.51016(19) 0.0407(11) Uani 0.446(5) 1 d D . P A 2
H29D H 0.3497 0.4572 0.5283 0.061 Uiso 0.446(5) 1 calc R U P A 2
H29E H 0.3137 0.3303 0.4661 0.061 Uiso 0.446(5) 1 calc R U P A 2
H29F H 0.4918 0.3907 0.5012 0.061 Uiso 0.446(5) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C13 1.2728(18) . ?
O2 C8 1.2378(18) . ?
O3 H3 0.8400 . ?
O3 C10 1.3155(19) . ?
O4 C10 1.2138(18) . ?
O6 C13 1.2328(18) . ?
O7 H7A 0.8702 . ?
O7 H7B 0.8697 . ?
O1 C2 1.3767(19) . ?
O1 C1 1.418(2) . ?
N2 H2 0.8800 . ?
N2 C8 1.3595(19) . ?
N2 C9 1.4465(18) . ?
N3 C14 1.5203(18) . ?
N3 C22 1.5183(17) . ?
N3 C18 1.5167(18) . ?
N3 C26 1.5194(19) . ?
N1 H1 0.8800 . ?
N1 C8 1.3652(19) . ?
N1 C5 1.4037(19) . ?
C5 C6 1.389(2) . ?
C5 C4 1.396(2) . ?
C13 C12 1.517(2) . ?
C10 C9 1.518(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(2) . ?
C9 H9 1.0000 . ?
C9 C11 1.5354(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.517(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.519(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(2) . ?
C2 C7 1.383(2) . ?
C2 C3 1.389(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.512(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.509(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.529(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(2) . ?
C7 H7 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.521(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.523(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(2) . ?
C3 H3A 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.518(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.504(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 H28C 0.9900 . ?
C28 H28D 0.9900 . ?
C28 C29A 1.337(4) . ?
C28 C29B 1.567(4) . ?
C29A H29A 0.9800 . ?
C29A H29B 0.9800 . ?
C29A H29C 0.9800 . ?
C29B H29D 0.9800 . ?
C29B H29E 0.9800 . ?
C29B H29F 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
C10 O3 H3 109.5 . . ?
H7A O7 H7B 104.5 . . ?
C2 O1 C1 117.02(14) . . ?
C8 N2 H2 119.2 . . ?
C8 N2 C9 121.54(12) . . ?
C9 N2 H2 119.2 . . ?
C22 N3 C14 106.00(10) . . ?
C22 N3 C26 111.18(11) . . ?
C18 N3 C14 111.10(11) . . ?
C18 N3 C22 111.56(11) . . ?
C18 N3 C26 106.08(11) . . ?
C26 N3 C14 111.01(11) . . ?
C8 N1 H1 115.5 . . ?
C8 N1 C5 128.91(12) . . ?
C5 N1 H1 115.5 . . ?
O2 C8 N2 121.99(13) . . ?
O2 C8 N1 124.94(13) . . ?
N2 C8 N1 113.08(12) . . ?
C6 C5 N1 116.43(13) . . ?
C6 C5 C4 118.50(14) . . ?
C4 C5 N1 125.07(13) . . ?
O5 C13 C12 116.53(12) . . ?
O6 C13 O5 124.37(13) . . ?
O6 C13 C12 119.09(13) . . ?
O3 C10 C9 114.63(12) . . ?
O4 C10 O3 124.29(14) . . ?
O4 C10 C9 120.94(14) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.38(14) . . ?
C7 C6 H6 119.3 . . ?
N2 C9 C10 113.28(12) . . ?
N2 C9 H9 108.2 . . ?
N2 C9 C11 109.05(11) . . ?
C10 C9 H9 108.2 . . ?
C10 C9 C11 109.69(11) . . ?
C11 C9 H9 108.2 . . ?
N3 C14 H14A 108.3 . . ?
N3 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 N3 115.92(12) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
N3 C22 H22A 108.2 . . ?
N3 C22 H22B 108.2 . . ?
N3 C22 C23 116.47(11) . . ?
H22A C22 H22B 107.3 . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C9 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C9 112.96(11) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
O1 C2 C7 124.87(15) . . ?
O1 C2 C3 115.92(15) . . ?
C7 C2 C3 119.21(14) . . ?
N3 C18 H18A 108.3 . . ?
N3 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 N3 115.95(12) . . ?
C19 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
N3 C26 H26A 108.3 . . ?
N3 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C27 C26 N3 115.93(12) . . ?
C27 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
C13 C12 C11 115.70(12) . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C22 C23 H23A 110.0 . . ?
C22 C23 H23B 110.0 . . ?
C22 C23 C24 108.38(12) . . ?
H23A C23 H23B 108.4 . . ?
C24 C23 H23A 110.0 . . ?
C24 C23 H23B 110.0 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14 C15 C16 109.30(12) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C6 C7 H7 120.1 . . ?
C2 C7 C6 119.80(14) . . ?
C2 C7 H7 120.1 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 C23 112.89(14) . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C18 C19 C20 109.76(14) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C15 111.42(14) . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.03(14) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 121.08(15) . . ?
C4 C3 H3A 119.5 . . ?
C26 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
C26 C27 C28 110.07(17) . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.83(17) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C27 C28 H28A 106.9 . . ?
C27 C28 H28B 106.9 . . ?
C27 C28 H28C 110.6 . . ?
C27 C28 H28D 110.6 . . ?
C27 C28 C29B 105.5(2) . . ?
H28A C28 H28B 106.7 . . ?
H28C C28 H28D 108.8 . . ?
C29A C28 C27 121.9(3) . . ?
C29A C28 H28A 106.9 . . ?
C29A C28 H28B 106.9 . . ?
C29B C28 H28C 110.6 . . ?
C29B C28 H28D 110.6 . . ?
C28 C29A H29A 109.5 . . ?
C28 C29A H29B 109.5 . . ?
C28 C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
C28 C29B H29D 109.5 . . ?
C28 C29B H29E 109.5 . . ?
C28 C29B H29F 109.5 . . ?
H29D C29B H29E 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 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
O5 C13 C12 C11 -175.37(13) . . . . ?
O3 C10 C9 N2 42.85(16) . . . . ?
O3 C10 C9 C11 -79.24(15) . . . . ?
O4 C10 C9 N2 -141.34(14) . . . . ?
O4 C10 C9 C11 96.57(16) . . . . ?
O6 C13 C12 C11 5.9(2) . . . . ?
O1 C2 C7 C6 178.72(14) . . . . ?
O1 C2 C3 C4 -179.23(15) . . . . ?
N2 C9 C11 C12 -177.85(13) . . . . ?
N3 C14 C15 C16 170.75(13) . . . . ?
N3 C22 C23 C24 177.11(13) . . . . ?
N3 C18 C19 C20 179.19(13) . . . . ?
N3 C26 C27 C28 -174.98(14) . . . . ?
N1 C5 C6 C7 179.72(13) . . . . ?
N1 C5 C4 C3 179.83(15) . . . . ?
C8 N2 C9 C10 54.88(18) . . . . ?
C8 N2 C9 C11 177.33(13) . . . . ?
C8 N1 C5 C6 172.25(14) . . . . ?
C8 N1 C5 C4 -7.7(2) . . . . ?
C5 N1 C8 O2 0.5(3) . . . . ?
C5 N1 C8 N2 -179.20(14) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C10 C9 C11 C12 -53.27(17) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
C9 N2 C8 O2 -5.8(2) . . . . ?
C9 N2 C8 N1 173.84(13) . . . . ?
C9 C11 C12 C13 -176.49(13) . . . . ?
C14 N3 C22 C23 178.29(12) . . . . ?
C14 N3 C18 C19 -58.01(16) . . . . ?
C14 N3 C26 C27 62.62(16) . . . . ?
C14 C15 C16 C17 -178.87(16) . . . . ?
C22 N3 C14 C15 -179.44(12) . . . . ?
C22 N3 C18 C19 60.03(16) . . . . ?
C22 N3 C26 C27 -55.12(17) . . . . ?
C22 C23 C24 C25 179.82(14) . . . . ?
C18 N3 C14 C15 -58.08(16) . . . . ?
C18 N3 C22 C23 57.23(16) . . . . ?
C18 N3 C26 C27 -176.58(13) . . . . ?
C18 C19 C20 C21 178.76(15) . . . . ?
C26 N3 C14 C15 59.71(16) . . . . ?
C26 N3 C22 C23 -60.98(16) . . . . ?
C26 N3 C18 C19 -178.75(12) . . . . ?
C26 C27 C28 C29A 176.9(2) . . . . ?
C26 C27 C28 C29B 102.1(2) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C3 C2 C7 C6 -0.6(2) . . . . ?
C1 O1 C2 C7 12.5(2) . . . . ?
C1 O1 C2 C3 -168.23(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.968
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_2024jrh0013_notwin
_database_code_depnum_ccdc_archive 'CCDC 2388585'
loop_
_audit_author_name
_audit_author_address
'Jennifer Hiscock'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_audit_creation_date             2024-03-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H15 F3 N2 O5'
_chemical_formula_sum            'C14 H15 F3 N2 O5'
_chemical_formula_weight         348.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2F3
_chemical_oxdiff_usercomment     '150 k lisa w 3-31-2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.781(3)
_cell_length_b                   10.9013(10)
_cell_length_c                   10.0416(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.477(10)
_cell_angle_gamma                90
_cell_volume                     3035.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.7980
_cell_measurement_theta_min      4.3140
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -7 0 0.0190
1 -1 -6 0.0365
-2 7 0 0.0532
-18 -1 0 0.0199
18 1 0 0.0180
0 0 7 0.1471

_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.4472 -6.9864 0.4018 -0.9795 -0.1824 0.0859
1.0009 -0.8274 -6.4773 -0.1374 -0.0242 -0.9902
-2.4958 7.0009 -0.0039 0.9828 0.1829 -0.0250
-17.8588 -0.9994 0.3737 -0.1828 0.9825 0.0363
17.8390 0.9927 -0.0777 0.1829 -0.9831 0.0091
-0.4461 0.0059 7.0070 0.0246 -0.0148 1.0747

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11086
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.473
_diffrn_reflns_theta_min         4.358
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -10.00   1.00   10.00    --  -41.91 125.00 120.00   46
  2  ω   -114.00 -18.00   1.00   10.00    --  -41.91 -38.00 -30.00   96
  3  ω    -86.00 -11.00   1.00   10.00    --  -41.91 125.00-150.00   75
  4  ω   -109.00 -17.00   1.00   10.00    --  -41.91 -38.00  60.00   92
  5  ω     55.00  96.00   1.00   10.00    --   41.91-125.00-180.00   41
  6  ω     69.00 113.00   1.00   22.50    --  103.72-125.00 -30.00   44
  7  ω     21.00 106.00   1.00   22.50    --  103.72 -94.00 120.00   85
  8  ω     67.00  94.00   1.00   22.50    --  103.72 -77.00 120.00   27
  9  ω     32.00 126.00   1.00   22.50    --  103.72 -45.00-150.00   94
 10  ω     55.00 118.00   1.00   22.50    --  103.72 -61.00 -30.00   63
 11  ω     42.00 116.00   1.00   22.50    --  103.72 -45.00 120.00   74
 12  ω     34.00 129.00   1.00   22.50    --  103.72 -30.00 -60.00   95
 13  ω     77.00 113.00   1.00   22.50    --  103.72-125.00-120.00   36
 14  ω    106.00 176.00   1.00   22.50    --  103.72  77.00 -90.00   70
 15  ω     52.00 105.00   1.00   22.50    --  103.72 -94.00 -30.00   53
 16  ω     81.00 113.00   1.00   22.50    --  103.72-125.00 120.00   32
 17  ω    145.00 172.00   1.00   22.50    --  103.72 125.00   0.00   27
 18  ω     17.00 170.00   1.00   22.50    --  103.72   0.00 -90.00  153
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024087000
_diffrn_orient_matrix_UB_12      0.1412438000
_diffrn_orient_matrix_UB_13      0.0035427000
_diffrn_orient_matrix_UB_21      -0.0554863000
_diffrn_orient_matrix_UB_22      0.0063425000
_diffrn_orient_matrix_UB_23      -0.0056452000
_diffrn_orient_matrix_UB_31      0.0013440000
_diffrn_orient_matrix_UB_32      -0.0030010000
_diffrn_orient_matrix_UB_33      0.1534653000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1938
_reflns_number_total             2932
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.1299
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1754P)²+31.1281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3830
_refine_ls_wR_factor_ref         0.4072
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C13(H13), C12(H12), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.7792(2) 0.8355(4) 0.8420(4) 0.0415(13) Uani 1 1 d . . . . .
H3 H 0.7915 0.7669 0.8610 0.062 Uiso 1 1 calc R U . . .
O5 O 0.68302(19) 1.1366(4) 0.5491(5) 0.0412(12) Uani 1 1 d . . . . .
O4 O 0.7464(2) 0.7358(4) 0.6623(5) 0.0410(12) Uani 1 1 d . . . . .
N1 N 0.7129(2) 0.9418(5) 0.5498(5) 0.0356(13) Uani 1 1 d . . . . .
H1 H 0.7129 0.8712 0.5073 0.043 Uiso 1 1 calc R U . . .
O2 O 0.8601(2) 0.7622(5) 0.6289(6) 0.0525(15) Uani 1 1 d . . . . .
F1 F 0.5462(2) 1.3729(5) -0.0025(6) 0.0773(18) Uani 1 1 d . . . . .
N2 N 0.6526(2) 0.9961(5) 0.3969(6) 0.0375(13) Uani 1 1 d . . . . .
H2 H 0.6520 0.9169 0.3801 0.045 Uiso 1 1 calc R U . . .
F3 F 0.5177(3) 1.2059(7) -0.0762(6) 0.095(2) Uani 1 1 d . . . . .
O1 O 0.8844(2) 0.9293(5) 0.7403(6) 0.0516(14) Uani 1 1 d . . . . .
C8 C 0.6221(3) 1.0693(6) 0.3132(6) 0.0357(15) Uani 1 1 d . . . . .
C6 C 0.7557(3) 0.8297(6) 0.7235(7) 0.0371(15) Uani 1 1 d . . . . .
C5 C 0.7444(3) 0.9571(6) 0.6688(6) 0.0347(15) Uani 1 1 d . . . . .
H5 H 0.7265 1.0032 0.7363 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6831(3) 1.0327(6) 0.5012(6) 0.0352(15) Uani 1 1 d . . . . .
C13 C 0.6272(3) 1.1947(7) 0.3013(8) 0.0453(18) Uani 1 1 d . . . . .
H13 H 0.6513 1.2369 0.3544 0.054 Uiso 1 1 calc R U . . .
C2 C 0.8583(3) 0.8712(6) 0.6442(7) 0.0411(16) Uani 1 1 d . . . . .
C4 C 0.7909(3) 1.0282(6) 0.6434(7) 0.0359(15) Uani 1 1 d . . . . .
H4A H 0.7820 1.1055 0.5966 0.043 Uiso 1 1 calc R U . . .
H4B H 0.8072 1.0501 0.7305 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5967(3) 1.2586(7) 0.2108(8) 0.0498(19) Uani 1 1 d . . . . .
H12 H 0.5998 1.3451 0.2032 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5620(3) 1.1984(8) 0.1322(8) 0.0503(19) Uani 1 1 d . . . . .
C3 C 0.8267(3) 0.9588(6) 0.5613(7) 0.0410(17) Uani 1 1 d . . . . .
H3A H 0.8086 0.9121 0.4900 0.049 Uiso 1 1 calc R U . . .
H3B H 0.8475 1.0188 0.5179 0.049 Uiso 1 1 calc R U . . .
F2 F 0.4873(3) 1.2930(11) 0.0883(8) 0.144(4) Uani 1 1 d . . . . .
C10 C 0.5568(4) 1.0739(8) 0.1452(9) 0.061(2) Uani 1 1 d . . . . .
H10 H 0.5325 1.0322 0.0922 0.074 Uiso 1 1 calc R U . . .
C9 C 0.5868(3) 1.0080(8) 0.2352(9) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.5831 0.9218 0.2433 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5282(3) 1.2682(9) 0.0394(9) 0.061(2) Uani 1 1 d . . . . .
C1 C 0.9150(4) 0.8519(9) 0.8339(10) 0.067(3) Uani 1 1 d . . . . .
H1A H 0.9407 0.8137 0.7856 0.101 Uiso 1 1 calc R U . . .
H1B H 0.8951 0.7879 0.8717 0.101 Uiso 1 1 calc R U . . .
H1C H 0.9293 0.9032 0.9060 0.101 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
O3 H3 0.8400 . ?
O3 C6 1.323(8) . ?
O5 C7 1.230(8) . ?
O4 C6 1.214(8) . ?
N1 H1 0.8800 . ?
N1 C5 1.448(8) . ?
N1 C7 1.362(9) . ?
O2 C2 1.199(9) . ?
F1 C14 1.325(11) . ?
N2 H2 0.8800 . ?
N2 C8 1.405(9) . ?
N2 C7 1.366(9) . ?
F3 C14 1.361(12) . ?
O1 C2 1.331(9) . ?
O1 C1 1.491(10) . ?
C8 C13 1.380(10) . ?
C8 C9 1.389(10) . ?
C6 C5 1.518(9) . ?
C5 H5 1.0000 . ?
C5 C4 1.542(10) . ?
C13 H13 0.9500 . ?
C13 C12 1.393(11) . ?
C2 C3 1.513(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.530(9) . ?
C12 H12 0.9500 . ?
C12 C11 1.374(12) . ?
C11 C10 1.372(13) . ?
C11 C14 1.491(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
F2 C14 1.294(12) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(12) . ?
C9 H9 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C6 O3 H3 109.5 . . ?
C5 N1 H1 118.8 . . ?
C7 N1 H1 118.8 . . ?
C7 N1 C5 122.4(6) . . ?
C8 N2 H2 116.0 . . ?
C7 N2 H2 116.0 . . ?
C7 N2 C8 128.0(6) . . ?
C2 O1 C1 116.9(6) . . ?
C13 C8 N2 123.5(6) . . ?
C13 C8 C9 120.0(7) . . ?
C9 C8 N2 116.4(6) . . ?
O3 C6 C5 111.2(6) . . ?
O4 C6 O3 125.0(6) . . ?
O4 C6 C5 123.7(6) . . ?
N1 C5 C6 107.2(5) . . ?
N1 C5 H5 108.4 . . ?
N1 C5 C4 113.1(5) . . ?
C6 C5 H5 108.4 . . ?
C6 C5 C4 111.3(6) . . ?
C4 C5 H5 108.4 . . ?
O5 C7 N1 123.0(6) . . ?
O5 C7 N2 123.6(6) . . ?
N1 C7 N2 113.4(6) . . ?
C8 C13 H13 120.3 . . ?
C8 C13 C12 119.4(7) . . ?
C12 C13 H13 120.3 . . ?
O2 C2 O1 122.7(7) . . ?
O2 C2 C3 125.5(7) . . ?
O1 C2 C3 111.7(6) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C3 C4 C5 114.8(6) . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 120.9(7) . . ?
C11 C12 H12 119.5 . . ?
C12 C11 C14 120.5(8) . . ?
C10 C11 C12 119.4(7) . . ?
C10 C11 C14 119.9(8) . . ?
C2 C3 C4 113.0(6) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C11 C10 H10 119.6 . . ?
C11 C10 C9 120.7(8) . . ?
C9 C10 H10 119.6 . . ?
C8 C9 C10 119.5(8) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
F1 C14 F3 103.0(8) . . ?
F1 C14 C11 113.7(8) . . ?
F3 C14 C11 111.9(8) . . ?
F2 C14 F1 107.4(9) . . ?
F2 C14 F3 106.2(9) . . ?
F2 C14 C11 113.8(8) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O3 C6 C5 N1 -171.7(6) . . . . ?
O3 C6 C5 C4 64.2(7) . . . . ?
O4 C6 C5 N1 11.9(10) . . . . ?
O4 C6 C5 C4 -112.2(8) . . . . ?
N1 C5 C4 C3 -70.0(7) . . . . ?
O2 C2 C3 C4 119.1(8) . . . . ?
N2 C8 C13 C12 176.9(7) . . . . ?
N2 C8 C9 C10 -176.9(8) . . . . ?
O1 C2 C3 C4 -60.0(8) . . . . ?
C8 N2 C7 O5 10.9(12) . . . . ?
C8 N2 C7 N1 -170.9(7) . . . . ?
C8 C13 C12 C11 -0.8(13) . . . . ?
C6 C5 C4 C3 50.7(7) . . . . ?
C5 N1 C7 O5 4.9(11) . . . . ?
C5 N1 C7 N2 -173.3(6) . . . . ?
C5 C4 C3 C2 -82.6(8) . . . . ?
C7 N1 C5 C6 157.3(6) . . . . ?
C7 N1 C5 C4 -79.7(8) . . . . ?
C7 N2 C8 C13 17.5(12) . . . . ?
C7 N2 C8 C9 -165.5(8) . . . . ?
C13 C8 C9 C10 0.2(14) . . . . ?
C13 C12 C11 C10 1.4(14) . . . . ?
C13 C12 C11 C14 177.6(8) . . . . ?
C12 C11 C10 C9 -1.1(15) . . . . ?
C12 C11 C14 F1 27.6(13) . . . . ?
C12 C11 C14 F3 143.9(9) . . . . ?
C12 C11 C14 F2 -95.7(12) . . . . ?
C11 C10 C9 C8 0.4(16) . . . . ?
C10 C11 C14 F1 -156.2(9) . . . . ?
C10 C11 C14 F3 -39.9(13) . . . . ?
C10 C11 C14 F2 80.5(13) . . . . ?
C9 C8 C13 C12 0.0(13) . . . . ?
C14 C11 C10 C9 -177.4(9) . . . . ?
C1 O1 C2 O2 -2.5(12) . . . . ?
C1 O1 C2 C3 176.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.617
# start Validation Reply Form
_vrf_PLAT084_2024jrh0013_notwin  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: There is evidence in the diffraction pattern of unresolved twinning by 180 degree 
rotations about both the a- and c-axes.  Despite several attempts to resolve the separate
components of twinning, it was not possible to obtain a suitable model.  Despite this
we are confident of the atomic assignment and chemical connectivity of the model.
The unresolved twinning should not significantly affect qualitative interpretation of the
supramolecular interactions present in the structure.
;
_vrf_PLAT340_2024jrh0013_notwin  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01109 Ang.  
RESPONSE: This is likely a result of the unresolved twinning and resultant poor quality
data as described above.  This issue is likely to also be responsible for the 
unusually high values in the witghting scheme and was the reason for omitting 
some of the worst 
fitting reflections
;
# end Validation Reply Form
####################################################################### 
# 
# 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_2024jrh0015_mono
_database_code_depnum_ccdc_archive 'CCDC 2388586'
loop_
_audit_author_name
_audit_author_address
'Jennifer Hiscock'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_audit_creation_date             2024-10-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H16 N2 O6'
_chemical_formula_sum            'C13 H16 N2 O6'
_chemical_formula_weight         296.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2F2
_chemical_oxdiff_usercomment     '150K 34-2'
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'

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

_cell_length_a                   27.123(3)
_cell_length_b                   6.2205(5)
_cell_length_c                   7.7852(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.642(10)
_cell_angle_gamma                90
_cell_volume                     1313.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      71.5080
_cell_measurement_theta_min      6.5010
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -4 0.0731
7 0 4 0.0731
3 -4 0 0.0508
-3 4 0 0.0508
14 1 -1 0.0020
-14 -1 1 0.0020

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.004
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0433 0.0067 -4.0012 -0.1002 0.5118 -0.7224
7.0433 -0.0067 4.0012 0.1002 -0.5118 0.7224
2.9046 -4.0108 0.0091 0.2232 -0.8317 -0.5215
-2.9046 4.0108 -0.0091 -0.2232 0.8317 0.5215
14.0301 0.9769 -1.0022 0.7944 0.1864 0.2526
-14.0301 -0.9769 1.0022 -0.7944 -0.1864 -0.2526

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.953
_diffrn_reflns_theta_min         4.892
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -20.00   1.00   12.50    --  -41.91 -57.00-150.00   91
  2  ω    -68.00  30.00   1.00   12.50    --  -41.91  57.00   0.00   98
  3  ω    -62.00  31.00   1.00   12.50    --  -41.91  57.00 120.00   93
  4  ω     47.00  73.00   1.00   12.50    --   41.91 -77.00  90.00   26
  5  ω     97.00 147.00   1.00   22.50    --  103.72 125.00 -60.00   50
  6  ω    103.00 159.00   1.00   22.50    --  103.72  77.00  60.00   56
  7  ω     39.00 122.00   1.00   22.50    --  103.72 -45.00   0.00   83
  8  ω    136.00 177.00   1.00   22.50    --  103.72  45.00   0.00   41
  9  ω     44.00 105.00   1.00   22.50    --  103.72 -94.00   0.00   61
 10  ω     81.00 106.00   1.00   22.50    --  103.72 -94.00  60.00   25
 11  ω     32.00 126.00   1.00   22.50    --  103.72 -61.00-150.00   94
 12  ω     86.00 164.00   1.00   22.50    --  103.72  45.00  30.00   78
 13  ω    113.00 173.00   1.00   22.50    --  103.72 125.00 -90.00   60
 14  ω     50.00 108.00   1.00   22.50    --  103.72-125.00-120.00   58
 15  ω    108.00 158.00   1.00   22.50    --  103.72  45.00 -60.00   50
 16  ω     82.00 121.00   1.00   22.50    --  103.72  45.00   0.00   39
 17  ω    148.00 173.00   1.00   22.50    --  103.72 125.00-150.00   25
 18  ω     78.00 108.00   1.00   22.50    --  103.72-103.00 -89.58   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0529600000
_diffrn_orient_matrix_UB_12      -0.0174444000
_diffrn_orient_matrix_UB_13      -0.0682082000
_diffrn_orient_matrix_UB_21      -0.0087151000
_diffrn_orient_matrix_UB_22      0.2008040000
_diffrn_orient_matrix_UB_23      -0.1122296000
_diffrn_orient_matrix_UB_31      0.0185675000
_diffrn_orient_matrix_UB_32      0.1438163000
_diffrn_orient_matrix_UB_33      0.1480991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1800
_reflns_number_total             2539
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.1379
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1819P)²+13.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3935
_refine_ls_wR_factor_ref         0.4113
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C7(H7), C4(H4), C3(H3A), C6(H6A)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2495(2) 0.4745(9) 0.5403(7) 0.0305(13) Uani 1 1 d . . . . .
O5 O 0.4427(2) 0.4543(10) 0.5600(7) 0.0325(14) Uani 1 1 d . . . . .
O3 O 0.2811(2) 0.6628(9) 0.9139(7) 0.0326(14) Uani 1 1 d . . . . .
H3 H 0.2765 0.7767 0.9694 0.049 Uiso 1 1 calc R U . . .
O6 O 0.5036(2) 0.5958(10) 0.7198(8) 0.0368(15) Uani 1 1 d . . . . .
H6 H 0.5187 0.5862 0.6264 0.055 Uiso 1 1 calc R U . . .
O4 O 0.3382(2) 0.8622(8) 0.7834(8) 0.0327(14) Uani 1 1 d . . . . .
O1 O 0.0473(2) -0.0660(9) 0.3729(8) 0.0356(14) Uani 1 1 d . . . . .
N1 N 0.2273(2) 0.1601(10) 0.6740(8) 0.0272(14) Uani 1 1 d . . . . .
H1 H 0.2367 0.0738 0.7578 0.033 Uiso 1 1 calc R U . . .
N2 N 0.3018(2) 0.3090(10) 0.7292(8) 0.0265(14) Uani 1 1 d . . . . .
H2 H 0.3085 0.1890 0.7846 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3187(3) 0.6885(11) 0.8104(9) 0.0252(16) Uani 1 1 d . . . . .
C5 C 0.1819(3) 0.1063(12) 0.5934(9) 0.0250(16) Uani 1 1 d . . . . .
C12 C 0.4274(3) 0.5389(13) 0.8552(10) 0.0301(18) Uani 1 1 d . . . . .
H12A H 0.4172 0.6904 0.8713 0.036 Uiso 1 1 calc R U . . .
H12B H 0.4477 0.4972 0.9563 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2581(3) 0.3225(11) 0.6417(9) 0.0249(16) Uani 1 1 d . . . . .
C2 C 0.0910(3) -0.0184(13) 0.4495(10) 0.0280(17) Uani 1 1 d . . . . .
C7 C 0.1181(3) -0.1616(13) 0.5541(10) 0.0299(17) Uani 1 1 d . . . . .
H7 H 0.1056 -0.3011 0.5776 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1546(3) 0.2520(12) 0.4912(10) 0.0270(17) Uani 1 1 d . . . . .
H4 H 0.1667 0.3930 0.4709 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4583(3) 0.5247(12) 0.6989(10) 0.0304(18) Uani 1 1 d . . . . .
C3 C 0.1101(3) 0.1868(13) 0.4211(10) 0.0315(18) Uani 1 1 d . . . . .
H3A H 0.0919 0.2846 0.3514 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3385(3) 0.4823(11) 0.7366(10) 0.0238(16) Uani 1 1 d . . . . .
H9 H 0.3509 0.5105 0.6183 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1632(3) -0.0972(13) 0.6226(11) 0.0315(18) Uani 1 1 d . . . . .
H6A H 0.1817 -0.1952 0.6912 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3812(3) 0.3980(13) 0.8496(11) 0.0317(18) Uani 1 1 d . . . . .
H11A H 0.3691 0.3807 0.9684 0.038 Uiso 1 1 calc R U . . .
H11B H 0.3906 0.2537 0.8076 0.038 Uiso 1 1 calc R U . . .
C1 C 0.0253(3) -0.2677(15) 0.4077(12) 0.039(2) Uani 1 1 d . . . . .
H1A H -0.0077 -0.2726 0.3553 0.058 Uiso 1 1 calc R U . . .
H1B H 0.0227 -0.2872 0.5321 0.058 Uiso 1 1 calc R U . . .
H1C H 0.0456 -0.3826 0.3596 0.058 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
O2 C8 1.252(9) . ?
O5 C13 1.236(10) . ?
O3 H3 0.8400 . ?
O3 C10 1.316(10) . ?
O6 H6 0.8400 . ?
O6 C13 1.315(10) . ?
O4 C10 1.223(9) . ?
O1 C2 1.354(10) . ?
O1 C1 1.416(11) . ?
N1 H1 0.8800 . ?
N1 C5 1.416(10) . ?
N1 C8 1.336(10) . ?
N2 H2 0.8800 . ?
N2 C8 1.363(10) . ?
N2 C9 1.467(10) . ?
C10 C9 1.507(10) . ?
C5 C4 1.411(11) . ?
C5 C6 1.383(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.488(12) . ?
C12 C11 1.529(12) . ?
C2 C7 1.407(11) . ?
C2 C3 1.396(11) . ?
C7 H7 0.9500 . ?
C7 C6 1.390(12) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(12) . ?
C3 H3A 0.9500 . ?
C9 H9 1.0000 . ?
C9 C11 1.539(10) . ?
C6 H6A 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C10 O3 H3 109.5 . . ?
C13 O6 H6 109.5 . . ?
C2 O1 C1 118.6(7) . . ?
C5 N1 H1 115.2 . . ?
C8 N1 H1 115.2 . . ?
C8 N1 C5 129.6(6) . . ?
C8 N2 H2 118.0 . . ?
C8 N2 C9 124.0(6) . . ?
C9 N2 H2 118.0 . . ?
O3 C10 C9 114.3(6) . . ?
O4 C10 O3 123.6(7) . . ?
O4 C10 C9 122.0(7) . . ?
C4 C5 N1 123.1(7) . . ?
C6 C5 N1 117.6(7) . . ?
C6 C5 C4 119.3(7) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C13 C12 C11 114.3(7) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
O2 C8 N1 125.2(7) . . ?
O2 C8 N2 121.2(7) . . ?
N1 C8 N2 113.7(6) . . ?
O1 C2 C7 124.4(7) . . ?
O1 C2 C3 117.1(7) . . ?
C3 C2 C7 118.6(7) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.4(7) . . ?
C6 C7 H7 120.3 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(7) . . ?
C3 C4 H4 120.5 . . ?
O5 C13 O6 122.4(8) . . ?
O5 C13 C12 123.2(8) . . ?
O6 C13 C12 114.4(7) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 C2 122.1(8) . . ?
C4 C3 H3A 119.0 . . ?
N2 C9 C10 113.3(6) . . ?
N2 C9 H9 109.1 . . ?
N2 C9 C11 106.1(6) . . ?
C10 C9 H9 109.1 . . ?
C10 C9 C11 109.9(6) . . ?
C11 C9 H9 109.1 . . ?
C5 C6 C7 121.6(8) . . ?
C5 C6 H6A 119.2 . . ?
C7 C6 H6A 119.2 . . ?
C12 C11 C9 115.6(7) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C9 C11 H11A 108.4 . . ?
C9 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O3 C10 C9 N2 25.1(9) . . . . ?
O3 C10 C9 C11 -93.4(8) . . . . ?
O4 C10 C9 N2 -159.1(7) . . . . ?
O4 C10 C9 C11 82.4(9) . . . . ?
O1 C2 C7 C6 178.4(8) . . . . ?
O1 C2 C3 C4 -179.3(7) . . . . ?
N1 C5 C4 C3 -178.4(7) . . . . ?
N1 C5 C6 C7 177.6(7) . . . . ?
N2 C9 C11 C12 171.5(7) . . . . ?
C10 C9 C11 C12 -65.5(9) . . . . ?
C5 N1 C8 O2 7.5(13) . . . . ?
C5 N1 C8 N2 -171.7(7) . . . . ?
C5 C4 C3 C2 0.6(12) . . . . ?
C8 N1 C5 C4 -17.6(12) . . . . ?
C8 N1 C5 C6 164.7(8) . . . . ?
C8 N2 C9 C10 58.7(9) . . . . ?
C8 N2 C9 C11 179.5(7) . . . . ?
C2 C7 C6 C5 1.3(12) . . . . ?
C7 C2 C3 C4 0.5(12) . . . . ?
C4 C5 C6 C7 -0.2(12) . . . . ?
C13 C12 C11 C9 -76.1(9) . . . . ?
C3 C2 C7 C6 -1.4(12) . . . . ?
C9 N2 C8 O2 10.6(11) . . . . ?
C9 N2 C8 N1 -170.2(7) . . . . ?
C6 C5 C4 C3 -0.8(12) . . . . ?
C11 C12 C13 O5 18.5(11) . . . . ?
C11 C12 C13 O6 -162.3(7) . . . . ?
C1 O1 C2 C7 4.2(12) . . . . ?
C1 O1 C2 C3 -176.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.790
####################################################################### 
# 
# 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_2024jrh0022a_auto_res
_database_code_depnum_ccdc_archive 'CCDC 2388587'
loop_
_audit_author_name
_audit_author_address
'Jennifer Hiscock'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H11 Br N2 O5, 7(H2 O), 2(C16 H36 N)'
_chemical_formula_sum            'C44 H97 Br N4 O12'
_chemical_formula_weight         954.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20H20N2O2Br
_chemical_oxdiff_usercomment     '150 K lisa w 35-3 '
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.3063(13)
_cell_length_b                   16.6092(12)
_cell_length_c                   33.619(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10780.2(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3647
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      56.2740
_cell_measurement_theta_min      3.7020
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             4160
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -2 -2 0.0274
5 2 2 0.0274
-4 5 -1 0.0482
4 -5 1 0.0482
1 0 -5 0.0099
-1 0 5 0.0099

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0000 -2.0000 -1.9997 -0.0463 -0.2337 -0.3809
5.0000 2.0000 1.9997 0.0463 0.2337 0.3809
-4.0001 5.0000 -1.0002 -0.1120 -0.5126 0.2086
4.0001 -5.0000 1.0002 0.1120 0.5126 -0.2086
1.0000 -0.0000 -5.0000 -0.2286 0.0817 0.0064
-1.0000 0.0000 5.0000 0.2286 -0.0817 -0.0064

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            28580
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         3.486
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -16.00   1.00   12.50    --  -42.16 -57.00  30.00   94
  2  ω    -54.00 -16.00   1.00   12.50    --  -42.16 125.00-180.00   38
  3  ω     14.00  50.00   1.00   12.50    --   42.16  19.00 150.00   36
  4  ω     80.00 177.00   1.00   20.00    --  103.72  30.00 120.00   97
  5  ω     44.00  70.00   1.00   20.00    --  103.72-125.00-180.00   26
  6  ω     83.00 111.00   1.00   20.00    --  103.72-125.00-180.00   28
  7  ω    104.00 172.00   1.00   20.00    --  103.72  77.00 -30.00   68
  8  ω     59.00 112.00   1.00   20.00    --  103.72-125.00 -30.00   53
  9  ω    138.00 168.00   1.00   20.00    --  103.72 125.00 -60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0026241000
_diffrn_orient_matrix_UB_12      -0.0154660000
_diffrn_orient_matrix_UB_13      0.0451911000
_diffrn_orient_matrix_UB_21      0.0675112000
_diffrn_orient_matrix_UB_22      -0.0490791000
_diffrn_orient_matrix_UB_23      -0.0028458000
_diffrn_orient_matrix_UB_31      0.0424427000
_diffrn_orient_matrix_UB_32      0.0771189000
_diffrn_orient_matrix_UB_33      0.0072074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5339
_reflns_number_total             9503
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         9503
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0867
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1405P)²+12.5390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2843
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C43-C44A \\sim C43-C44B
 with sigma of 0.02
3. Others
 Sof(H43C)=Sof(H43D)=Sof(C44B)=Sof(H44D)=Sof(H44E)=Sof(H44F)=1-FVAR(1)
 Sof(H43A)=Sof(H43B)=Sof(C44A)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
 Fixed Sof: H8A(0.5) H8B(0.5) H9A(0.5) H9B(0.5)
4.a Free rotating group:
 O12(H12A,H12B), O7(H7A,H7B), O8(H8A,H8B), O6(H6A,H6B), O9(H9A,H9B), O13(H13C,
 H13D), O11(H11C,H11D), O10(H10C,H10D)
4.b Ternary CH refined with riding coordinates:
 C8(H8)
4.c Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C17(H17A,H17B), C33(H33A,H33B), C13(H13A,H13B), C37(H37A,
 H37B), C22(H22A,H22B), C41(H41A,H41B), C10(H10A,H10B), C29(H29A,H29B),
 C25(H25A,H25B), C34(H34A,H34B), C23(H23A,H23B), C18(H18A,H18B), C14(H14A,H14B),
  C11(H11A,H11B), C26(H26A,H26B), C38(H38A,H38B), C35(H35A,H35B), C42(H42A,
 H42B), C30(H30A,H30B), C15(H15A,H15B), C39(H39A,H39B), C19(H19A,H19B),
 C31(H31A,H31B), C43(H43A,H43B), C43(H43C,H43D), C27(H27A,H27B)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C2(H2A), C5(H5), C6(H6)
4.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C36(H36A,H36B,H36C), C16(H16A,H16B,
 H16C), C40(H40A,H40B,H40C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C),
 C44A(H44A,H44B,H44C), C44B(H44D,H44E,H44F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04493(4) 0.46488(6) 0.56784(3) 0.1020(4) Uani 1 1 d . . . . .
O1 O 0.31182(19) 0.5837(2) 0.43848(10) 0.0574(9) Uani 1 1 d . . . . .
O12 O 0.62647(19) 0.4328(2) 0.31798(11) 0.0584(9) Uani 1 1 d G . . . .
H12A H 0.5821 0.4394 0.3146 0.088 Uiso 1 1 d G U . . .
H12B H 0.6405 0.4105 0.2960 0.088 Uiso 1 1 d G U . . .
O3 O 0.5741(2) 0.6190(2) 0.41081(12) 0.0618(10) Uani 1 1 d . . . . .
O2 O 0.5544(2) 0.5413(2) 0.46337(11) 0.0613(10) Uani 1 1 d . . . . .
O7 O 0.3482(2) 0.3537(3) 0.25645(11) 0.0642(10) Uani 1 1 d G . . . .
H7A H 0.3543 0.3789 0.2789 0.096 Uiso 1 1 d G U . . .
H7B H 0.3871 0.3287 0.2523 0.096 Uiso 1 1 d G U . . .
O8 O 0.5000 0.3239(3) 0.2500 0.0614(14) Uani 1 2 d GS T P . .
H8A H 0.4606 0.3211 0.2375 0.092 Uiso 0.5 1 d G U P . .
H8B H 0.4902 0.3483 0.2722 0.092 Uiso 0.5 1 d G U P . .
N3 N 0.77260(19) 0.7755(2) 0.38765(11) 0.0404(9) Uani 1 1 d . . . . .
O6 O 0.2628(2) 0.4891(3) 0.37132(12) 0.0665(11) Uani 1 1 d G . . . .
H6A H 0.2990 0.4762 0.3572 0.100 Uiso 1 1 d G U . . .
H6B H 0.2791 0.5188 0.3904 0.100 Uiso 1 1 d G U . . .
N4 N 0.7029(2) 0.7596(2) 0.15908(12) 0.0455(10) Uani 1 1 d . . . . .
O5 O 0.3747(2) 0.4332(3) 0.32719(11) 0.0710(11) Uani 1 1 d . . . . .
N2 N 0.4202(2) 0.5417(3) 0.45555(12) 0.0523(11) Uani 1 1 d . . . . .
H2 H 0.4444 0.5104 0.4715 0.063 Uiso 1 1 calc R U . . .
N1 N 0.3291(2) 0.5060(3) 0.49428(13) 0.0552(11) Uani 1 1 d . . . . .
H1 H 0.3611 0.4802 0.5079 0.066 Uiso 1 1 calc R U . . .
O4 O 0.4844(2) 0.4333(3) 0.31084(13) 0.0829(13) Uani 1 1 d . . . . .
C21 C 0.7243(2) 0.7431(3) 0.41960(13) 0.0408(10) Uani 1 1 d . . . . .
H21A H 0.6909 0.7060 0.4068 0.049 Uiso 1 1 calc R U . . .
H21B H 0.7521 0.7111 0.4386 0.049 Uiso 1 1 calc R U . . .
C17 C 0.8303(2) 0.8263(3) 0.40577(15) 0.0449(11) Uani 1 1 d . . . . .
H17A H 0.8606 0.8454 0.3840 0.054 Uiso 1 1 calc R U . . .
H17B H 0.8092 0.8743 0.4183 0.054 Uiso 1 1 calc R U . . .
O9 O 0.5000 0.5456(5) 0.2500 0.097(2) Uani 1 2 d GS T P . .
H9A H 0.4621 0.5438 0.2361 0.145 Uiso 0.5 1 d G U P . .
H9B H 0.5284 0.5139 0.2374 0.145 Uiso 0.5 1 d G U P . .
C33 C 0.6816(3) 0.8353(3) 0.18107(14) 0.0460(11) Uani 1 1 d . . . . .
H33A H 0.6933 0.8824 0.1643 0.055 Uiso 1 1 calc R U . . .
H33B H 0.7094 0.8392 0.2057 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3516(3) 0.5459(3) 0.46124(15) 0.0517(13) Uani 1 1 d . . . . .
C13 C 0.8025(3) 0.7024(3) 0.36626(14) 0.0460(11) Uani 1 1 d . . . . .
H13A H 0.8298 0.6709 0.3857 0.055 Uiso 1 1 calc R U . . .
H13B H 0.7634 0.6681 0.3575 0.055 Uiso 1 1 calc R U . . .
C37 C 0.6646(3) 0.7526(3) 0.11919(14) 0.0510(12) Uani 1 1 d . . . . .
H37A H 0.6759 0.6998 0.1071 0.061 Uiso 1 1 calc R U . . .
H37B H 0.6141 0.7533 0.1244 0.061 Uiso 1 1 calc R U . . .
O13 O 0.6657(4) 0.5772(4) 0.35302(17) 0.125(2) Uani 1 1 d G . . A 1
H13C H 0.6391 0.5781 0.3739 0.187 Uiso 1 1 d G U . A 1
H13D H 0.6902 0.5335 0.3557 0.187 Uiso 1 1 d G U . A 1
C22 C 0.6839(3) 0.8054(3) 0.44288(15) 0.0518(13) Uani 1 1 d . . . . .
H22A H 0.6511 0.8331 0.4249 0.062 Uiso 1 1 calc R U . . .
H22B H 0.7162 0.8463 0.4536 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4572(3) 0.5851(3) 0.42489(15) 0.0524(13) Uani 1 1 d . . . . .
H8 H 0.4425 0.6428 0.4264 0.063 Uiso 1 1 calc R U . . .
C41 C 0.7810(3) 0.7673(3) 0.15201(16) 0.0515(12) Uani 1 1 d . . . . .
H41A H 0.7897 0.8175 0.1369 0.062 Uiso 1 1 calc R U . . .
H41B H 0.8043 0.7727 0.1781 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2625(3) 0.5007(3) 0.50915(16) 0.0526(13) Uani 1 1 d . . . . .
C9 C 0.5354(3) 0.5814(3) 0.43414(16) 0.0528(13) Uani 1 1 d . . . . .
C10 C 0.4413(3) 0.5549(3) 0.38311(15) 0.0535(13) Uani 1 1 d . . . . .
H10A H 0.3917 0.5647 0.3772 0.064 Uiso 1 1 calc R U . . .
H10B H 0.4690 0.5861 0.3637 0.064 Uiso 1 1 calc R U . . .
O11 O 0.5126(3) 0.7389(3) 0.36231(19) 0.1003(16) Uani 1 1 d G . . . .
H11C H 0.5148 0.7127 0.3399 0.150 Uiso 1 1 d G U . . .
H11D H 0.5446 0.7170 0.3771 0.150 Uiso 1 1 d G U . . .
C29 C 0.6858(3) 0.6845(3) 0.18301(16) 0.0549(13) Uani 1 1 d . . . . .
H29A H 0.6348 0.6785 0.1839 0.066 Uiso 1 1 calc R U . . .
H29B H 0.7045 0.6372 0.1686 0.066 Uiso 1 1 calc R U . . .
C25 C 0.7357(3) 0.8305(3) 0.35854(15) 0.0515(12) Uani 1 1 d . . . . .
H25A H 0.7175 0.8777 0.3732 0.062 Uiso 1 1 calc R U . . .
H25B H 0.7697 0.8505 0.3389 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2557(3) 0.4782(3) 0.54903(16) 0.0566(14) Uani 1 1 d . . . . .
H3 H 0.2962 0.4688 0.5644 0.068 Uiso 1 1 calc R U . . .
C34 C 0.6051(3) 0.8405(3) 0.19221(16) 0.0566(13) Uani 1 1 d . . . . .
H34A H 0.5764 0.8292 0.1685 0.068 Uiso 1 1 calc R U . . .
H34B H 0.5944 0.7994 0.2126 0.068 Uiso 1 1 calc R U . . .
C23 C 0.6441(3) 0.7670(4) 0.47687(16) 0.0579(14) Uani 1 1 d . . . . .
H23A H 0.6113 0.8070 0.4879 0.070 Uiso 1 1 calc R U . . .
H23B H 0.6167 0.7214 0.4663 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8748(3) 0.7853(3) 0.43612(19) 0.0615(15) Uani 1 1 d . . . . .
H18A H 0.8889 0.7318 0.4260 0.074 Uiso 1 1 calc R U . . .
H18B H 0.8477 0.7771 0.4608 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8480(3) 0.7188(3) 0.33051(17) 0.0604(14) Uani 1 1 d . . . . .
H14A H 0.8854 0.7569 0.3377 0.072 Uiso 1 1 calc R U . . .
H14B H 0.8203 0.7429 0.3088 0.072 Uiso 1 1 calc R U . . .
C2 C 0.1924(3) 0.4694(3) 0.56643(18) 0.0620(15) Uani 1 1 d . . . . .
H2A H 0.1890 0.4544 0.5936 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2016(3) 0.5147(3) 0.48698(17) 0.0632(15) Uani 1 1 d . . . . .
H5 H 0.2045 0.5304 0.4599 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4567(3) 0.4657(3) 0.37773(16) 0.0598(14) Uani 1 1 d . . . . .
H11A H 0.4301 0.4338 0.3973 0.072 Uiso 1 1 calc R U . . .
H11B H 0.5066 0.4554 0.3821 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1372(3) 0.5053(4) 0.50498(19) 0.0675(16) Uani 1 1 d . . . . .
H6 H 0.0961 0.5147 0.4902 0.081 Uiso 1 1 calc R U . . .
C26 C 0.6764(3) 0.7911(4) 0.33650(17) 0.0647(15) Uani 1 1 d . . . . .
H26A H 0.6411 0.7723 0.3557 0.078 Uiso 1 1 calc R U . . .
H26B H 0.6937 0.7438 0.3216 0.078 Uiso 1 1 calc R U . . .
C38 C 0.6815(4) 0.8190(3) 0.08896(16) 0.0682(17) Uani 1 1 d . . . . .
H38A H 0.6754 0.8724 0.1015 0.082 Uiso 1 1 calc R U . . .
H38B H 0.7303 0.8140 0.0803 0.082 Uiso 1 1 calc R U . . .
C1 C 0.1333(3) 0.4825(3) 0.5443(2) 0.0666(16) Uani 1 1 d . . . . .
C35 C 0.5873(3) 0.9237(3) 0.20832(17) 0.0615(14) Uani 1 1 d . . . . .
H35A H 0.6217 0.9388 0.2288 0.074 Uiso 1 1 calc R U . . .
H35B H 0.5412 0.9215 0.2213 0.074 Uiso 1 1 calc R U . . .
C42 C 0.8136(3) 0.6977(4) 0.12969(18) 0.0655(15) Uani 1 1 d . . . . .
H42A H 0.7883 0.6885 0.1045 0.079 Uiso 1 1 calc R U . . .
H42B H 0.8104 0.6480 0.1459 0.079 Uiso 1 1 calc R U . . .
C20 C 0.9869(3) 0.8001(4) 0.47425(19) 0.0702(17) Uani 1 1 d . . . . .
H20A H 0.9959 0.7435 0.4677 0.105 Uiso 1 1 calc R U . . .
H20B H 0.9669 0.8036 0.5010 0.105 Uiso 1 1 calc R U . . .
H20C H 1.0304 0.8304 0.4734 0.105 Uiso 1 1 calc R U . . .
C12 C 0.4364(3) 0.4412(4) 0.33563(18) 0.0646(15) Uani 1 1 d . . . . .
O10 O 0.5696(4) 0.6670(4) 0.2943(2) 0.128(2) Uani 1 1 d G . . . .
H10C H 0.5413 0.6888 0.2772 0.192 Uiso 1 1 d G U . . .
H10D H 0.5670 0.6156 0.2895 0.192 Uiso 1 1 d G U . . .
C30 C 0.7130(4) 0.6824(4) 0.22530(18) 0.0714(17) Uani 1 1 d . . . . .
H30A H 0.6891 0.7241 0.2412 0.086 Uiso 1 1 calc R U . . .
H30B H 0.7631 0.6951 0.2252 0.086 Uiso 1 1 calc R U . . .
C15 C 0.8788(4) 0.6386(4) 0.3171(2) 0.0733(18) Uani 1 1 d . . . . .
H15A H 0.8408 0.5998 0.3124 0.088 Uiso 1 1 calc R U . . .
H15B H 0.9082 0.6168 0.3388 0.088 Uiso 1 1 calc R U . . .
C39 C 0.6337(4) 0.8117(4) 0.05294(17) 0.0719(18) Uani 1 1 d . . . . .
H39A H 0.6538 0.8425 0.0305 0.086 Uiso 1 1 calc R U . . .
H39B H 0.6311 0.7545 0.0448 0.086 Uiso 1 1 calc R U . . .
C24 C 0.6899(4) 0.7367(4) 0.51001(17) 0.0754(18) Uani 1 1 d . . . . .
H24A H 0.7203 0.6942 0.4998 0.113 Uiso 1 1 calc R U . . .
H24B H 0.6611 0.7151 0.5315 0.113 Uiso 1 1 calc R U . . .
H24C H 0.7181 0.7812 0.5203 0.113 Uiso 1 1 calc R U . . .
C19 C 0.9383(3) 0.8340(4) 0.4454(2) 0.0743(18) Uani 1 1 d . . . . .
H19A H 0.9636 0.8433 0.4202 0.089 Uiso 1 1 calc R U . . .
H19B H 0.9231 0.8872 0.4554 0.089 Uiso 1 1 calc R U . . .
C36 C 0.5862(4) 0.9883(4) 0.1761(2) 0.088(2) Uani 1 1 d . . . . .
H36A H 0.5528 0.9732 0.1554 0.132 Uiso 1 1 calc R U . . .
H36B H 0.6324 0.9932 0.1644 0.132 Uiso 1 1 calc R U . . .
H36C H 0.5726 1.0399 0.1879 0.132 Uiso 1 1 calc R U . . .
C31 C 0.7019(4) 0.6004(4) 0.2446(2) 0.085(2) Uani 1 1 d . . . . .
H31A H 0.7035 0.6067 0.2738 0.102 Uiso 1 1 calc R U . . .
H31B H 0.6551 0.5806 0.2375 0.102 Uiso 1 1 calc R U . . .
C43 C 0.8894(4) 0.7162(5) 0.1208(2) 0.088(2) Uani 1 1 d D . . . .
H43A H 0.9061 0.6734 0.1027 0.106 Uiso 0.492(13) 1 calc R U P B 1
H43B H 0.8901 0.7670 0.1054 0.106 Uiso 0.492(13) 1 calc R U P B 1
H43C H 0.8921 0.7656 0.1044 0.106 Uiso 0.508(13) 1 calc R U P B 2
H43D H 0.9139 0.7270 0.1461 0.106 Uiso 0.508(13) 1 calc R U P B 2
C16 C 0.9225(4) 0.6463(4) 0.2791(2) 0.088(2) Uani 1 1 d . . . . .
H16A H 0.8931 0.6649 0.2572 0.132 Uiso 1 1 calc R U . . .
H16B H 0.9424 0.5938 0.2724 0.132 Uiso 1 1 calc R U . . .
H16C H 0.9599 0.6852 0.2835 0.132 Uiso 1 1 calc R U . . .
C27 C 0.6438(4) 0.8519(4) 0.3075(2) 0.082(2) Uani 1 1 d . . . . .
H27A H 0.6805 0.8741 0.2902 0.098 Uiso 1 1 calc R U . . .
H27B H 0.6100 0.8235 0.2904 0.098 Uiso 1 1 calc R U . . .
C40 C 0.5617(5) 0.8420(5) 0.0608(2) 0.106(3) Uani 1 1 d . . . . .
H40A H 0.5354 0.8426 0.0359 0.159 Uiso 1 1 calc R U . . .
H40B H 0.5641 0.8967 0.0717 0.159 Uiso 1 1 calc R U . . .
H40C H 0.5387 0.8065 0.0800 0.159 Uiso 1 1 calc R U . . .
C28 C 0.6078(5) 0.9200(5) 0.3283(3) 0.109(3) Uani 1 1 d . . . . .
H28A H 0.5850 0.9544 0.3086 0.163 Uiso 1 1 calc R U . . .
H28B H 0.6419 0.9518 0.3432 0.163 Uiso 1 1 calc R U . . .
H28C H 0.5732 0.8984 0.3467 0.163 Uiso 1 1 calc R U . . .
C32 C 0.7517(5) 0.5417(5) 0.2329(3) 0.103(3) Uani 1 1 d . . . . .
H32A H 0.7491 0.5333 0.2041 0.155 Uiso 1 1 calc R U . . .
H32B H 0.7422 0.4909 0.2467 0.155 Uiso 1 1 calc R U . . .
H32C H 0.7982 0.5606 0.2400 0.155 Uiso 1 1 calc R U . . .
C44A C 0.9405(6) 0.7243(9) 0.1514(4) 0.077(4) Uani 0.492(13) 1 d D . P B 1
H44A H 0.9413 0.6754 0.1677 0.115 Uiso 0.492(13) 1 calc R U P B 1
H44B H 0.9291 0.7706 0.1682 0.115 Uiso 0.492(13) 1 calc R U P B 1
H44C H 0.9861 0.7325 0.1393 0.115 Uiso 0.492(13) 1 calc R U P B 1
C44B C 0.9230(9) 0.6537(10) 0.1009(5) 0.115(7) Uani 0.508(13) 1 d D . P B 2
H44D H 0.9732 0.6620 0.1022 0.173 Uiso 0.508(13) 1 calc R U P B 2
H44E H 0.9081 0.6527 0.0731 0.173 Uiso 0.508(13) 1 calc R U P B 2
H44F H 0.9112 0.6023 0.1136 0.173 Uiso 0.508(13) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.902(7) . ?
O1 C7 1.253(6) . ?
O12 H12A 0.8704 . ?
O12 H12B 0.8709 . ?
O3 C9 1.252(7) . ?
O2 C9 1.243(6) . ?
O7 H7A 0.8709 . ?
O7 H7B 0.8699 . ?
O8 H8A 0.8704 . ?
O8 H8B 0.8697 . ?
N3 C21 1.521(6) . ?
N3 C17 1.524(6) . ?
N3 C13 1.525(6) . ?
N3 C25 1.517(6) . ?
O6 H6A 0.8707 . ?
O6 H6B 0.8694 . ?
N4 C33 1.515(6) . ?
N4 C37 1.536(6) . ?
N4 C41 1.531(7) . ?
N4 C29 1.521(6) . ?
O5 C12 1.233(7) . ?
N2 H2 0.8800 . ?
N2 C7 1.341(7) . ?
N2 C8 1.446(7) . ?
N1 H1 0.8800 . ?
N1 C7 1.365(7) . ?
N1 C4 1.382(7) . ?
O4 C12 1.253(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.514(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.496(7) . ?
O9 H9A 0.8699 . ?
O9 H9B 0.8696 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.526(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(7) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.535(7) . ?
O13 H13C 0.8703 . ?
O13 H13D 0.8700 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.517(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.543(7) . ?
C8 C10 1.523(7) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.517(8) . ?
C4 C3 1.398(7) . ?
C4 C5 1.411(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.522(7) . ?
O11 H11C 0.8690 . ?
O11 H11D 0.8701 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.512(8) . ?
C3 H3 0.9500 . ?
C3 C2 1.363(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.523(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.509(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.501(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.527(8) . ?
C2 H2A 0.9500 . ?
C2 C1 1.379(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(8) . ?
C6 H6 0.9500 . ?
C6 C1 1.379(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.537(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.527(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.524(9) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.525(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.462(9) . ?
O10 H10C 0.8714 . ?
O10 H10D 0.8700 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.524(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.536(8) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.501(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.423(10) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 H43C 0.9900 . ?
C43 H43D 0.9900 . ?
C43 C44A 1.432(13) . ?
C43 C44B 1.394(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.500(10) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C44A H44A 0.9800 . ?
C44A H44B 0.9800 . ?
C44A H44C 0.9800 . ?
C44B H44D 0.9800 . ?
C44B H44E 0.9800 . ?
C44B H44F 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
H12A O12 H12B 104.4 . . ?
H7A O7 H7B 104.4 . . ?
H8A O8 H8B 104.5 . . ?
C21 N3 C17 111.2(3) . . ?
C21 N3 C13 106.4(3) . . ?
C17 N3 C13 110.6(4) . . ?
C25 N3 C21 112.4(4) . . ?
C25 N3 C17 105.6(4) . . ?
C25 N3 C13 110.7(4) . . ?
H6A O6 H6B 104.4 . . ?
C33 N4 C37 111.0(4) . . ?
C33 N4 C41 105.9(4) . . ?
C33 N4 C29 111.3(4) . . ?
C41 N4 C37 110.2(4) . . ?
C29 N4 C37 107.2(4) . . ?
C29 N4 C41 111.4(4) . . ?
C7 N2 H2 117.9 . . ?
C7 N2 C8 124.3(4) . . ?
C8 N2 H2 117.9 . . ?
C7 N1 H1 115.8 . . ?
C7 N1 C4 128.4(4) . . ?
C4 N1 H1 115.8 . . ?
N3 C21 H21A 108.3 . . ?
N3 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C22 C21 N3 116.1(4) . . ?
C22 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
N3 C17 H17A 108.2 . . ?
N3 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 N3 116.2(4) . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
H9A O9 H9B 104.5 . . ?
N4 C33 H33A 108.4 . . ?
N4 C33 H33B 108.4 . . ?
N4 C33 C34 115.5(4) . . ?
H33A C33 H33B 107.5 . . ?
C34 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
O1 C7 N2 123.0(5) . . ?
O1 C7 N1 123.1(5) . . ?
N2 C7 N1 113.9(4) . . ?
N3 C13 H13A 108.1 . . ?
N3 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C14 C13 N3 116.8(4) . . ?
C14 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
N4 C37 H37A 108.5 . . ?
N4 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C38 C37 N4 114.9(4) . . ?
C38 C37 H37A 108.5 . . ?
C38 C37 H37B 108.5 . . ?
H13C O13 H13D 104.5 . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C21 C22 C23 111.3(4) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
N2 C8 H8 107.7 . . ?
N2 C8 C9 108.6(4) . . ?
N2 C8 C10 113.2(4) . . ?
C9 C8 H8 107.7 . . ?
C10 C8 H8 107.7 . . ?
C10 C8 C9 111.7(5) . . ?
N4 C41 H41A 108.5 . . ?
N4 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C42 C41 N4 114.9(4) . . ?
C42 C41 H41A 108.5 . . ?
C42 C41 H41B 108.5 . . ?
N1 C4 C3 116.8(5) . . ?
N1 C4 C5 125.0(5) . . ?
C3 C4 C5 118.2(6) . . ?
O3 C9 C8 116.1(5) . . ?
O2 C9 O3 125.8(5) . . ?
O2 C9 C8 118.1(5) . . ?
C8 C10 H10A 109.0 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C8 113.0(4) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H11C O11 H11D 104.6 . . ?
N4 C29 H29A 108.3 . . ?
N4 C29 H29B 108.3 . . ?
H29A C29 H29B 107.4 . . ?
C30 C29 N4 116.1(4) . . ?
C30 C29 H29A 108.3 . . ?
C30 C29 H29B 108.3 . . ?
N3 C25 H25A 108.7 . . ?
N3 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 N3 114.2(4) . . ?
C26 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C33 C34 H34A 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C35 C34 C33 111.0(5) . . ?
C35 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.6(5) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C17 C18 C19 111.5(5) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C13 C14 H14A 110.2 . . ?
C13 C14 H14B 110.2 . . ?
C13 C14 C15 107.6(5) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
C3 C2 H2A 120.2 . . ?
C3 C2 C1 119.7(6) . . ?
C1 C2 H2A 120.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
C10 C11 C12 108.7(5) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C5 C6 H6 120.1 . . ?
C1 C6 C5 119.9(6) . . ?
C1 C6 H6 120.1 . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
C25 C26 C27 109.6(5) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C37 C38 H38A 109.7 . . ?
C37 C38 H38B 109.7 . . ?
H38A C38 H38B 108.2 . . ?
C39 C38 C37 109.9(5) . . ?
C39 C38 H38A 109.7 . . ?
C39 C38 H38B 109.7 . . ?
C2 C1 Br1 119.7(5) . . ?
C2 C1 C6 120.9(6) . . ?
C6 C1 Br1 119.4(5) . . ?
C34 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C34 C35 C36 112.9(5) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C41 C42 H42A 109.7 . . ?
C41 C42 H42B 109.7 . . ?
C41 C42 C43 110.0(5) . . ?
H42A C42 H42B 108.2 . . ?
C43 C42 H42A 109.7 . . ?
C43 C42 H42B 109.7 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
O5 C12 O4 123.4(5) . . ?
O5 C12 C11 119.4(5) . . ?
O4 C12 C11 117.1(5) . . ?
H10C O10 H10D 104.5 . . ?
C29 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
C29 C30 C31 111.7(5) . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C14 C15 C16 112.7(5) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C38 C39 H39A 109.0 . . ?
C38 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
C40 C39 C38 113.1(6) . . ?
C40 C39 H39A 109.0 . . ?
C40 C39 H39B 109.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C19 H19A 108.0 . . ?
C18 C19 H19B 108.0 . . ?
C20 C19 C18 117.1(6) . . ?
C20 C19 H19A 108.0 . . ?
C20 C19 H19B 108.0 . . ?
H19A C19 H19B 107.3 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C30 C31 H31A 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C32 C31 C30 113.6(7) . . ?
C32 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C42 C43 H43A 106.7 . . ?
C42 C43 H43B 106.7 . . ?
C42 C43 H43C 109.0 . . ?
C42 C43 H43D 109.0 . . ?
H43A C43 H43B 106.6 . . ?
H43C C43 H43D 107.8 . . ?
C44A C43 C42 122.6(8) . . ?
C44A C43 H43A 106.7 . . ?
C44A C43 H43B 106.7 . . ?
C44B C43 C42 112.9(10) . . ?
C44B C43 H43C 109.0 . . ?
C44B C43 H43D 109.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 C26 113.0(6) . . ?
C28 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C43 C44A H44A 109.5 . . ?
C43 C44A H44B 109.5 . . ?
C43 C44A H44C 109.5 . . ?
H44A C44A H44B 109.5 . . ?
H44A C44A H44C 109.5 . . ?
H44B C44A H44C 109.5 . . ?
C43 C44B H44D 109.5 . . ?
C43 C44B H44E 109.5 . . ?
C43 C44B H44F 109.5 . . ?
H44D C44B H44E 109.5 . . ?
H44D C44B H44F 109.5 . . ?
H44E C44B H44F 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
N3 C21 C22 C23 -173.4(4) . . . . ?
N3 C17 C18 C19 167.9(5) . . . . ?
N3 C13 C14 C15 173.2(5) . . . . ?
N3 C25 C26 C27 -179.1(5) . . . . ?
N4 C33 C34 C35 -171.3(4) . . . . ?
N4 C37 C38 C39 -172.7(5) . . . . ?
N4 C41 C42 C43 174.2(5) . . . . ?
N4 C29 C30 C31 -172.0(5) . . . . ?
N2 C8 C9 O3 -177.6(4) . . . . ?
N2 C8 C9 O2 3.2(6) . . . . ?
N2 C8 C10 C11 -57.2(6) . . . . ?
N1 C4 C3 C2 -178.5(5) . . . . ?
N1 C4 C5 C6 178.2(5) . . . . ?
C21 N3 C17 C18 57.5(5) . . . . ?
C21 N3 C13 C14 175.0(4) . . . . ?
C21 N3 C25 C26 -59.6(5) . . . . ?
C21 C22 C23 C24 69.9(6) . . . . ?
C17 N3 C21 C22 64.1(5) . . . . ?
C17 N3 C13 C14 -64.0(6) . . . . ?
C17 N3 C25 C26 179.0(4) . . . . ?
C17 C18 C19 C20 -179.0(6) . . . . ?
C33 N4 C37 C38 64.4(6) . . . . ?
C33 N4 C41 C42 -179.3(4) . . . . ?
C33 N4 C29 C30 -52.9(6) . . . . ?
C33 C34 C35 C36 72.4(7) . . . . ?
C7 N2 C8 C9 166.3(4) . . . . ?
C7 N2 C8 C10 -69.0(6) . . . . ?
C7 N1 C4 C3 -160.7(5) . . . . ?
C7 N1 C4 C5 20.7(8) . . . . ?
C13 N3 C21 C22 -175.4(4) . . . . ?
C13 N3 C17 C18 -60.6(5) . . . . ?
C13 N3 C25 C26 59.3(5) . . . . ?
C13 C14 C15 C16 176.1(6) . . . . ?
C37 N4 C33 C34 61.6(5) . . . . ?
C37 N4 C41 C42 -59.2(5) . . . . ?
C37 N4 C29 C30 -174.5(5) . . . . ?
C37 C38 C39 C40 76.2(7) . . . . ?
C8 N2 C7 O1 5.5(8) . . . . ?
C8 N2 C7 N1 -173.9(4) . . . . ?
C8 C10 C11 C12 177.8(5) . . . . ?
C41 N4 C33 C34 -178.9(4) . . . . ?
C41 N4 C37 C38 -52.5(6) . . . . ?
C41 N4 C29 C30 65.0(6) . . . . ?
C41 C42 C43 C44A 65.7(10) . . . . ?
C41 C42 C43 C44B 178.8(9) . . . . ?
C4 N1 C7 O1 -1.6(8) . . . . ?
C4 N1 C7 N2 177.8(5) . . . . ?
C4 C3 C2 C1 0.4(8) . . . . ?
C4 C5 C6 C1 -0.1(9) . . . . ?
C9 C8 C10 C11 65.8(6) . . . . ?
C10 C8 C9 O3 56.9(6) . . . . ?
C10 C8 C9 O2 -122.4(5) . . . . ?
C10 C11 C12 O5 -75.0(7) . . . . ?
C10 C11 C12 O4 102.3(7) . . . . ?
C29 N4 C33 C34 -57.7(5) . . . . ?
C29 N4 C37 C38 -173.9(5) . . . . ?
C29 N4 C41 C42 59.5(6) . . . . ?
C29 C30 C31 C32 79.5(8) . . . . ?
C25 N3 C21 C22 -54.0(5) . . . . ?
C25 N3 C17 C18 179.6(4) . . . . ?
C25 N3 C13 C14 52.7(6) . . . . ?
C25 C26 C27 C28 -67.2(8) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C3 C2 C1 Br1 176.8(4) . . . . ?
C3 C2 C1 C6 -0.9(8) . . . . ?
C5 C4 C3 C2 0.2(8) . . . . ?
C5 C6 C1 Br1 -177.0(4) . . . . ?
C5 C6 C1 C2 0.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.838
