# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cis_syn-(AA)-5
_database_code_depnum_ccdc_archive 'CCDC 2176601'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H29 Br1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   6.36017(18)
_cell_length_b                   7.8529(2)
_cell_length_c                   20.1551(10)
_cell_angle_alpha                91.523(4)
_cell_angle_beta                 91.016(4)
_cell_angle_gamma                93.880(2)
_cell_volume                     1003.82(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16122
_cell_measurement_temperature    129(14)
_cell_measurement_theta_max      74.2050
_cell_measurement_theta_min      4.3050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.973
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 1 0.0206
0 -2 -1 0.0244
1 0 0 0.1499
-1 0 0 0.0937
0 0 1 0.0806
0 0 -1 0.0752

_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.045
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
-0.0015 2.0142 0.9163 0.3347 -0.2264 -0.0116
0.0015 -2.0142 -0.9163 -0.3347 0.2264 0.0116
0.9988 0.0006 0.0058 0.0116 -0.0009 -0.2423
-0.9988 -0.0006 -0.0058 -0.0116 0.0009 0.2423
-0.0022 0.0147 0.9946 -0.0265 -0.0714 -0.0023
0.0022 -0.0147 -0.9946 0.0265 0.0714 0.0023

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20722
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.639
_diffrn_reflns_theta_min         2.193
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      129(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  35.00   0.50    0.51    --   14.00  29.00  -9.83   50
  2  ω     11.00  36.00   0.50    0.51    --   18.00  28.00   3.95   50
  3  ω     10.00  35.00   0.50    0.51    --   14.00  29.00  33.91   50
  4  ω     15.00  41.00   0.50    0.51    --   18.00  28.00  54.87   52
  5  ω     37.00  99.00   0.50    0.51    --   62.00  22.00-122.79  124
  6  ω     50.00  84.00   0.50    0.51    --   81.25  21.00-125.36   68
  7  ω     34.00  62.00   0.50    0.51    --   66.78  21.00-146.73   56
  8  ω     49.00  74.00   0.50    0.51    --   81.25  20.00-159.92   50
  9  ω     50.00  98.00   0.50    0.51    --   81.25  21.00  16.43   96
 10  ω     54.00 101.00   0.50    0.51    --   81.25  20.00  45.12   94
 11  ω     48.00  82.00   0.50    0.51    --   81.25  21.00 169.95   68
 12  ω    102.00 128.00   0.50    0.51    --   81.25  19.00 145.85   52
 13  ω    102.00 132.00   0.50    0.51    --   81.25  21.00 169.95   60
 14  ω     49.00  75.00   0.50    0.51    --   81.25  19.00 145.85   52
 15  ω     45.00 116.00   0.50    0.51    --   81.25  17.00 105.79  142
 16  ω     35.00  84.00   0.50    0.51    --   76.98   0.00  90.00   98
 17  ω     46.00  92.00   0.50    0.51    --   81.25  16.00 -19.52   92
 18  ω    106.00 131.00   0.50    0.51    --   81.25  16.00 -19.52   50
 19  ω     49.00 112.00   0.50    0.51    --   81.25  19.00 -82.52  126
 20  ω     35.00  93.00   0.50    0.51    --   76.98   0.00 -60.00  116
 21  ω     47.00 108.00   0.50    0.51    --   76.98   0.00   0.00  122
 22  ω     89.00 116.00   0.50    0.51    --   76.98   0.00  90.00   54
 23  ω    103.00 129.00   0.50    0.51    --   81.25  20.00-159.92   52
 24  ω     82.00 114.00   0.50    0.51    --   76.98   0.00-180.00   64
 25  ω     37.00  79.00   0.50    0.51    --   76.98   0.00-180.00   84
 26  ω     -8.00  40.00   0.50    0.51    --  -10.00  28.00-163.63   96
 27  ω    -52.00 -19.00   0.50    0.51    --  -59.37   0.00-180.00   66
 28  ω    -17.00  10.00   0.50    0.51    --  -26.00  51.00-116.71   54
 29  ω    -15.00  10.00   0.50    0.51    --  -22.00  44.00 -40.82   50
 30  ω   -101.00 -61.00   0.50    0.51    --  -59.37   0.00-180.00   80
 31  ω   -101.00 -57.00   0.50    0.51    --  -59.37   0.00 -90.00   88
 32  ω    -51.00 -18.00   0.50    0.51    --  -59.37   0.00 -90.00   66
 33  ω   -100.00 -75.00   0.50    0.51    --  -59.37   0.00   0.00   50
 34  ω   -100.00 -72.00   0.50    0.51    --  -59.37   0.00 150.00   56
 35  ω    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00 111.42   50
 36  ω    -44.00 -19.00   0.50    0.51    --  -26.00 -27.00 143.97   50
 37  ω    -51.00 -26.00   0.50    0.51    --  -42.00 -25.00 -50.45   50
 38  ω    -48.00 -23.00   0.50    0.51    --  -34.00 -26.00 -70.83   50
 39  ω    -51.00 -26.00   0.50    0.51    --  -42.00 -25.00 -90.03   50
 40  ω    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00-162.89   50
 41  ω    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00-134.33   50
 42  ω    -85.00 -39.00   0.50    0.51    --  -59.37 125.00  60.00   92
 43  ω    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00 131.29   50
 44  ω   -102.00 -66.00   0.50    0.51    --  -59.37 -15.00  60.00   72
 45  ω    -62.00 -37.00   0.50    0.51    --  -58.00 -23.00 158.17   50
 46  ω    -70.00 -41.00   0.50    0.51    --  -66.50 -22.00   6.14   58
 47  ω    -70.00 -40.00   0.50    0.51    --  -66.50 -22.00 -28.19   60
 48  ω    -70.00 -45.00   0.50    0.51    --  -66.50 -22.00 -57.23   50
 49  ω    -62.00 -37.00   0.50    0.51    --  -58.00 -23.00-173.77   50
 50  ω    -53.00 -27.00   0.50    0.51    --  -59.37 -15.00  60.00   52
 51  ω     37.00 112.00   0.50    0.51    --   81.25-129.00  99.07  150
 52  ω     38.00  98.00   0.50    0.51    --   76.98-125.00  60.00  120
 53  ω     36.00  95.00   0.50    0.51    --   76.98-125.00  30.00  118
 54  ω     41.00 109.00   0.50    0.51    --   76.98-125.00 150.00  136
 55  ω     35.00  81.00   0.50    0.51    --   76.98-125.00   0.00   92
 56  ω     79.00 109.00   0.50    0.51    --   76.98-125.00 -90.00   60
 57  ω     36.00  61.00   0.50    0.51    --   76.98-125.00-120.00   50
 58  ω     37.00  86.00   0.50    0.51    --   76.98-125.00-180.00   98
 59  ω     81.00 107.00   0.50    0.51    --   76.98-125.00-120.00   52
 60  ω     40.00  73.00   0.50    0.51    --   76.98-125.00-150.00   66
 61  ω     35.00  72.00   0.50    0.51    --   76.98-125.00 -90.00   74
 62  ω     76.00 101.00   0.50    0.51    --   76.98-125.00 -60.00   50
 63  ω     40.00  71.00   0.50    0.51    --   76.98-125.00 -60.00   62
 64  ω     40.00  76.00   0.50    0.51    --   81.25 -95.00-141.71   72
 65  ω     36.00 105.00   0.50    0.51    --   76.98-125.00 -30.00  138
 66  ω     18.00  70.00   0.50    0.51    --   59.80 -94.00 -60.00  104
 67  ω     18.00  71.00   0.50    0.51    --   59.80 -94.00   0.00  106
 68  ω     35.00  75.00   0.50    0.51    --   76.98-125.00 120.00   80
 69  ω     82.00 108.00   0.50    0.51    --   76.98-125.00 120.00   52
 70  ω     58.00  86.00   0.50    0.51    --   81.25 -83.00 148.25   56
 71  ω     19.00  70.00   0.50    0.51    --   59.80 -94.00  90.00  102
 72  ω     18.00  56.00   0.50    0.51    --   59.80 -94.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116417000
_diffrn_orient_matrix_UB_12      0.1795205000
_diffrn_orient_matrix_UB_13      -0.0293002000
_diffrn_orient_matrix_UB_21      -0.0004440000
_diffrn_orient_matrix_UB_22      -0.0802674000
_diffrn_orient_matrix_UB_23      -0.0705869000
_diffrn_orient_matrix_UB_31      -0.2425434000
_diffrn_orient_matrix_UB_32      -0.0046598000
_diffrn_orient_matrix_UB_33      -0.0027763000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3709
_reflns_number_total             3968
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.994
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.033
_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)+(0.0242P)²+1.3337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C24(H24A,H24B,H24C)
;
_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
Br1 Br 0.77654(5) 0.87747(4) 0.02160(2) 0.04738(11) Uani 1 1 d . . . . .
O9 O 0.4301(2) 0.12105(19) 0.15653(7) 0.0272(3) Uani 1 1 d . . . . .
O10 O 0.1664(2) 0.28384(16) 0.18445(6) 0.0199(3) Uani 1 1 d . . . . .
O15 O -0.0667(2) 0.15288(16) 0.34025(6) 0.0176(3) Uani 1 1 d . . . . .
O22 O -0.1780(2) -0.23050(16) 0.35417(6) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.6373(4) 0.6865(3) 0.06203(10) 0.0317(5) Uani 1 1 d . . . . .
C3 C 0.7300(4) 0.5334(3) 0.05962(11) 0.0344(5) Uani 1 1 d . . . . .
H3 H 0.861199 0.524305 0.038469 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6296(3) 0.3921(3) 0.08844(10) 0.0292(5) Uani 1 1 d . . . . .
H4 H 0.691424 0.285345 0.086803 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4381(3) 0.4072(3) 0.11974(9) 0.0211(4) Uani 1 1 d . . . . .
C6 C 0.3480(3) 0.5629(3) 0.12140(10) 0.0248(4) Uani 1 1 d . . . . .
H6 H 0.217054 0.572914 0.142636 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4469(4) 0.7044(3) 0.09238(10) 0.0316(5) Uani 1 1 d . . . . .
H7 H 0.384932 0.811162 0.093368 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3467(3) 0.2543(2) 0.15415(9) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.0964(3) 0.1612(2) 0.23440(9) 0.0180(4) Uani 1 1 d . . . . .
H11 H 0.223351 0.107654 0.252120 0.022 Uiso 1 1 calc R U . . .
C12 C 0.0087(3) 0.2688(2) 0.29042(9) 0.0187(4) Uani 1 1 d . . . . .
C13 C -0.1579(3) 0.3849(2) 0.26608(10) 0.0234(4) Uani 1 1 d . . . . .
H13A H -0.262933 0.318065 0.238248 0.035 Uiso 1 1 calc R U . . .
H13B H -0.090502 0.476363 0.240076 0.035 Uiso 1 1 calc R U . . .
H13C H -0.227148 0.434840 0.304297 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1881(3) 0.3754(3) 0.32570(10) 0.0267(4) Uani 1 1 d . . . . .
H14A H 0.130620 0.448799 0.360014 0.040 Uiso 1 1 calc R U . . .
H14B H 0.264159 0.446429 0.293482 0.040 Uiso 1 1 calc R U . . .
H14C H 0.285032 0.299633 0.346308 0.040 Uiso 1 1 calc R U . . .
C16 C -0.2691(3) 0.0630(2) 0.32988(9) 0.0165(4) Uani 1 1 d . . . . .
H16 H -0.352581 0.125855 0.297183 0.020 Uiso 1 1 calc R U . . .
C17 C -0.3768(3) 0.0680(2) 0.39678(9) 0.0204(4) Uani 1 1 d . . . . .
H17A H -0.375111 0.187334 0.414057 0.024 Uiso 1 1 calc R U . . .
H17B H -0.525437 0.022819 0.391570 0.024 Uiso 1 1 calc R U . . .
C18 C -0.2608(3) -0.0397(2) 0.44526(9) 0.0199(4) Uani 1 1 d . . . . .
H18A H -0.113763 0.008917 0.451413 0.024 Uiso 1 1 calc R U . . .
H18B H -0.329655 -0.035724 0.488883 0.024 Uiso 1 1 calc R U . . .
C19 C -0.2594(3) -0.2244(2) 0.42064(9) 0.0183(4) Uani 1 1 d . . . . .
C20 C -0.4764(3) -0.3201(3) 0.42497(10) 0.0256(4) Uani 1 1 d . . . . .
H20A H -0.582381 -0.254977 0.402996 0.038 Uiso 1 1 calc R U . . .
H20B H -0.512379 -0.333998 0.471683 0.038 Uiso 1 1 calc R U . . .
H20C H -0.473340 -0.432757 0.402993 0.038 Uiso 1 1 calc R U . . .
C21 C -0.1021(3) -0.3185(3) 0.46117(10) 0.0264(4) Uani 1 1 d . . . . .
H21A H -0.105218 -0.437872 0.445469 0.040 Uiso 1 1 calc R U . . .
H21B H -0.139701 -0.313998 0.508095 0.040 Uiso 1 1 calc R U . . .
H21C H 0.039784 -0.264305 0.456019 0.040 Uiso 1 1 calc R U . . .
C23 C -0.2517(3) -0.1201(2) 0.30356(9) 0.0158(3) Uani 1 1 d . . . . .
C24 C -0.4648(3) -0.1887(3) 0.27390(10) 0.0219(4) Uani 1 1 d . . . . .
H24A H -0.462342 -0.311708 0.264658 0.033 Uiso 1 1 calc R U . . .
H24B H -0.492510 -0.130546 0.232548 0.033 Uiso 1 1 calc R U . . .
H24C H -0.576177 -0.167835 0.305511 0.033 Uiso 1 1 calc R U . . .
C25 C -0.0830(3) -0.1313(2) 0.25023(9) 0.0188(4) Uani 1 1 d . . . . .
H25A H -0.118286 -0.235624 0.222520 0.023 Uiso 1 1 calc R U . . .
H25B H 0.053689 -0.146036 0.272917 0.023 Uiso 1 1 calc R U . . .
C26 C -0.0525(3) 0.0204(2) 0.20371(9) 0.0187(4) Uani 1 1 d . . . . .
H26A H 0.004919 -0.019539 0.161140 0.022 Uiso 1 1 calc R U . . .
H26B H -0.190774 0.066194 0.194208 0.022 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.899(2) . ?
O9 C8 1.207(2) . ?
O10 C8 1.340(2) . ?
O10 C11 1.466(2) . ?
O15 C12 1.440(2) . ?
O15 C16 1.434(2) . ?
O22 C19 1.446(2) . ?
O22 C23 1.448(2) . ?
C2 C3 1.375(4) . ?
C2 C7 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 C6 1.385(3) . ?
C5 C8 1.491(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.528(3) . ?
C11 C26 1.518(3) . ?
C12 C13 1.527(3) . ?
C12 C14 1.523(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.524(2) . ?
C16 C23 1.532(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.522(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.521(3) . ?
C19 C20 1.531(3) . ?
C19 C21 1.522(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 C24 1.530(2) . ?
C23 C25 1.537(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.539(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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
C8 O10 C11 116.27(14) . . ?
C16 O15 C12 118.41(13) . . ?
C19 O22 C23 120.99(13) . . ?
C3 C2 Br1 118.47(17) . . ?
C3 C2 C7 122.0(2) . . ?
C7 C2 Br1 119.57(18) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C8 117.19(18) . . ?
C6 C5 C4 119.71(19) . . ?
C6 C5 C8 122.97(18) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 118.5(2) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
O9 C8 O10 123.79(17) . . ?
O9 C8 C5 123.69(18) . . ?
O10 C8 C5 112.46(16) . . ?
O10 C11 H11 108.0 . . ?
O10 C11 C12 105.13(14) . . ?
O10 C11 C26 110.93(15) . . ?
C12 C11 H11 108.0 . . ?
C26 C11 H11 108.0 . . ?
C26 C11 C12 116.46(15) . . ?
O15 C12 C11 107.14(14) . . ?
O15 C12 C13 113.35(15) . . ?
O15 C12 C14 103.65(15) . . ?
C13 C12 C11 112.76(15) . . ?
C14 C12 C11 109.69(16) . . ?
C14 C12 C13 109.83(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O15 C16 H16 108.9 . . ?
O15 C16 C17 105.83(14) . . ?
O15 C16 C23 112.31(14) . . ?
C17 C16 H16 108.9 . . ?
C17 C16 C23 111.92(15) . . ?
C23 C16 H16 108.9 . . ?
C16 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 C16 109.15(15) . . ?
C18 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.64(15) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
O22 C19 C18 109.72(14) . . ?
O22 C19 C20 112.14(15) . . ?
O22 C19 C21 103.67(14) . . ?
C18 C19 C20 112.26(16) . . ?
C18 C19 C21 110.33(16) . . ?
C21 C19 C20 108.38(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O22 C23 C16 112.21(14) . . ?
O22 C23 C24 111.47(14) . . ?
O22 C23 C25 102.57(14) . . ?
C16 C23 C25 112.20(14) . . ?
C24 C23 C16 109.24(15) . . ?
C24 C23 C25 109.00(15) . . ?
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 . . ?
C23 C25 H25A 108.0 . . ?
C23 C25 H25B 108.0 . . ?
C23 C25 C26 117.14(15) . . ?
H25A C25 H25B 107.3 . . ?
C26 C25 H25A 108.0 . . ?
C26 C25 H25B 108.0 . . ?
C11 C26 C25 111.36(15) . . ?
C11 C26 H26A 109.4 . . ?
C11 C26 H26B 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 -179.48(16) . . . . ?
Br1 C2 C7 C6 179.82(16) . . . . ?
O10 C11 C12 O15 178.73(13) . . . . ?
O10 C11 C12 C13 53.34(19) . . . . ?
O10 C11 C12 C14 -69.39(18) . . . . ?
O10 C11 C26 C25 165.68(14) . . . . ?
O15 C16 C17 C18 -67.72(18) . . . . ?
O15 C16 C23 O22 73.09(18) . . . . ?
O15 C16 C23 C24 -162.76(14) . . . . ?
O15 C16 C23 C25 -41.8(2) . . . . ?
O22 C23 C25 C26 -154.85(15) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 -175.44(18) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C8 O9 0.6(3) . . . . ?
C4 C5 C8 O10 177.93(17) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C6 C5 C8 O9 -175.32(19) . . . . ?
C6 C5 C8 O10 2.0(3) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C8 O10 C11 C12 140.66(16) . . . . ?
C8 O10 C11 C26 -92.65(18) . . . . ?
C8 C5 C6 C7 175.56(18) . . . . ?
C11 O10 C8 O9 14.1(3) . . . . ?
C11 O10 C8 C5 -163.31(15) . . . . ?
C12 O15 C16 C17 -137.82(15) . . . . ?
C12 O15 C16 C23 99.78(17) . . . . ?
C12 C11 C26 C25 -74.2(2) . . . . ?
C16 O15 C12 C11 -79.81(18) . . . . ?
C16 O15 C12 C13 45.2(2) . . . . ?
C16 O15 C12 C14 164.24(15) . . . . ?
C16 C17 C18 C19 -59.5(2) . . . . ?
C16 C23 C25 C26 -34.2(2) . . . . ?
C17 C16 C23 O22 -45.8(2) . . . . ?
C17 C16 C23 C24 78.36(18) . . . . ?
C17 C16 C23 C25 -160.66(15) . . . . ?
C17 C18 C19 O22 53.41(19) . . . . ?
C17 C18 C19 C20 -72.0(2) . . . . ?
C17 C18 C19 C21 167.01(16) . . . . ?
C19 O22 C23 C16 43.5(2) . . . . ?
C19 O22 C23 C24 -79.39(19) . . . . ?
C19 O22 C23 C25 164.12(14) . . . . ?
C23 O22 C19 C18 -46.8(2) . . . . ?
C23 O22 C19 C20 78.6(2) . . . . ?
C23 O22 C19 C21 -164.68(15) . . . . ?
C23 C16 C17 C18 54.9(2) . . . . ?
C23 C25 C26 C11 85.0(2) . . . . ?
C24 C23 C25 C26 86.89(19) . . . . ?
C26 C11 C12 O15 55.5(2) . . . . ?
C26 C11 C12 C13 -69.9(2) . . . . ?
C26 C11 C12 C14 167.39(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 3.680
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_trans_syn-(AA)-5
_database_code_depnum_ccdc_archive 'CCDC 2176602'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br O4 C21 H29'
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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6941(3)
_cell_length_b                   8.2180(2)
_cell_length_c                   46.3766(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4075.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    40320
_cell_measurement_temperature    296.0(3)
_cell_measurement_theta_max      72.8040
_cell_measurement_theta_min      2.8140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0879
-1 -1 0 0.1709
-1 1 1 0.1041
1 -1 -1 0.1405
0 0 -1 0.0439
0 0 1 0.0200

_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.064
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
1.0022 1.0011 -0.0063 0.1144 0.1980 -0.0610
-1.0022 -1.0011 0.0063 -0.1144 -0.1980 0.0610
-0.9921 1.0050 0.9872 0.0704 0.0974 0.2065
0.9921 -1.0050 -0.9872 -0.0704 -0.0974 -0.2065
-0.0044 -0.0047 -1.0002 -0.0296 0.0149 -0.0026
0.0044 0.0047 1.0002 0.0296 -0.0149 0.0026

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0076
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            69471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.231
_diffrn_reflns_theta_min         3.813
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -18.00   0.50    2.00    --  -59.37  94.00 -61.00  108
  2  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  60.00   52
  3  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -30.00   52
  4  ω    -85.00 -35.00   0.50    2.00    --  -59.37 125.00  90.00  100
  5  ω    -85.00 -35.00   0.50    2.00    --  -59.37 125.00-150.00  100
  6  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00   0.00   52
  7  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00-150.00   52
  8  ω     39.00 123.00   0.50    2.00    --   73.96  15.00  90.00  168
  9  ω     32.00  86.00   0.50    2.00    --   73.96 -94.00-150.00  108
 10  ω     32.00  86.00   0.50    2.00    --   73.96 -94.00 -30.00  108
 11  ω     32.00  86.00   0.50    2.00    --   73.96 -94.00 -90.00  108
 12  ω     39.00 124.00   0.50    2.00    --   74.41  15.00   0.00  170
 13  ω     33.00  87.00   0.50    2.00    --   74.41 -94.00  60.00  108
 14  ω    -50.00 -24.00   0.50    2.00    --  -42.00 -25.00 -71.28   52
 15  ω    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00  17.92   50
 16  ω    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00 104.27   50
 17  ω    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00-169.84   50
 18  ω    -62.00 -37.00   0.50    2.00    --  -58.00 -23.00 -13.92   50
 19  ω    -62.00 -37.00   0.50    2.00    --  -58.00 -23.00-104.70   50
 20  ω   -101.00 -76.00   0.50    2.00    --  -59.37   0.00 -90.00   50
 21  ω   -100.00 -75.00   0.50    2.00    --  -59.37   0.00 120.00   50
 22  ω   -101.00 -76.00   0.50    2.00    --  -59.37   0.00 -30.00   50
 23  ω     68.00  93.00   0.50    2.00    --   60.10-125.00 -60.00   50
 24  ω    -68.00 -42.00   0.50    2.00    --  -66.50  83.00-150.29   52
 25  ω    -69.00 -35.00   0.50    2.00    --  -66.50  83.00  87.52   68
 26  ω    -62.00 -30.00   0.50    2.00    --  -66.50  82.00  -6.18   64
 27  ω    -71.00 -45.00   0.50    2.00    --  -66.50 -22.00 146.35   52
 28  ω    -70.00 -43.00   0.50    2.00    --  -66.50 -22.00  62.87   54
 29  ω     41.00  66.00   0.50    2.00    --   67.03  22.00  70.65   50
 30  ω     43.00  70.00   0.50    2.00    --   67.03  22.00-108.84   54
 31  ω     35.00  70.00   0.50    2.00    --   73.96-125.00  30.00   70
 32  ω     54.00  80.00   0.50    2.00    --   73.96 -94.00  60.00   52
 33  ω     55.00 107.00   0.50    2.00    --   73.96-125.00 -30.00  104
 34  ω     58.00  84.00   0.50    2.00    --   73.96-123.00 111.00   52
 35  ω     50.00  84.00   0.50    2.00    --   73.96 -94.00 150.00   68
 36  ω     32.00  57.00   0.50    2.00    --   73.96 -94.00-180.00   50
 37  ω     82.00 107.00   0.50    2.00    --   73.96-125.00  30.00   50
 38  ω     38.00 108.00   0.50    2.00    --   74.41-125.00 150.00  140
 39  ω     33.00  86.00   0.50    2.00    --   74.41   0.00-180.00  106
 40  ω     85.00 118.00   0.50    2.00    --   79.15  21.00-151.85   66
 41  ω     46.00  79.00   0.50    2.00    --   79.15  21.00-151.85   66
 42  ω     92.00 129.00   0.50    2.00    --   79.15-152.00 -92.06   74
 43  ω     61.00 121.00   0.50    2.00    --   79.15  17.00 -87.09  120
 44  ω     53.00  86.00   0.50    2.00    --   79.15-152.00 -92.06   66
 45  ω     34.00 107.00   0.50    2.00    --   79.15-115.00  59.45  146
 46  ω    -20.00   6.00   0.50    2.00    --  -26.00  56.00 121.28   52
 47  ω    -29.00   3.00   0.50    2.00    --  -34.00  59.00  90.45   64
 48  ω    -29.00   3.00   0.50    2.00    --  -34.00  59.00  34.32   64
 49  ω    -51.00 -24.00   0.50    2.00    --  -42.00 -25.00 -27.85   54
 50  ω    -56.00 -30.00   0.50    2.00    --  -50.00 -24.00 -56.23   52
 51  ω    -56.00 -30.00   0.50    2.00    --  -50.00 -24.00 -91.85   52
 52  ω    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00 167.60   54
 53  ω    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00-165.90   54
 54  ω    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00  15.37   54
 55  ω    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00  78.87   54
 56  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -60.00   52
 57  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 150.00   52
 58  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  30.00   52
 59  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00-180.00   52
 60  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -90.00   52
 61  ω   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  90.00   52
 62  ω    -71.00 -40.00   0.50    2.00    --  -66.50 -22.00-130.27   62
 63  ω     41.00  71.00   0.50    2.00    --   67.03  22.00 156.05   60
 64  ω     33.00 116.00   0.50    2.00    --   74.41   0.00-150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0366851000
_diffrn_orient_matrix_UB_12      0.0777725000
_diffrn_orient_matrix_UB_13      0.0290266000
_diffrn_orient_matrix_UB_21      0.0428711000
_diffrn_orient_matrix_UB_22      0.1547863000
_diffrn_orient_matrix_UB_23      -0.0158609000
_diffrn_orient_matrix_UB_31      -0.1325216000
_diffrn_orient_matrix_UB_32      0.0718000000
_diffrn_orient_matrix_UB_33      0.0028766000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3775
_reflns_number_total             3965
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.051
_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)+(0.0476P)²+3.2520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1094
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_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
Br1 Br 0.63352(4) 0.13539(5) 0.51462(2) 0.09452(18) Uani 1 1 d . . . . .
O8 O 0.67100(16) 0.5111(2) 0.38359(3) 0.0556(4) Uani 1 1 d . . . . .
O9 O 0.48952(13) 0.61456(17) 0.39993(3) 0.0431(3) Uani 1 1 d . . . . .
O15 O 0.38902(12) 0.98937(16) 0.36455(3) 0.0368(3) Uani 1 1 d . . . . .
O22 O 0.55736(13) 0.97500(16) 0.29561(3) 0.0386(3) Uani 1 1 d . . . . .
C1 C 0.6132(2) 0.2449(3) 0.47889(5) 0.0545(6) Uani 1 1 d . . . . .
C2 C 0.7046(2) 0.2310(3) 0.45857(5) 0.0568(6) Uani 1 1 d . . . . .
H2 H 0.775577 0.164158 0.461933 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6922(2) 0.3157(3) 0.43294(5) 0.0501(5) Uani 1 1 d . . . . .
H3 H 0.754629 0.305387 0.418476 0.060 Uiso 1 1 calc R U . . .
C4 C 0.58966(19) 0.4157(2) 0.42814(4) 0.0393(4) Uani 1 1 d . . . . .
C5 C 0.4969(2) 0.4244(3) 0.44877(5) 0.0522(5) Uani 1 1 d . . . . .
H5 H 0.424929 0.489519 0.445451 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5086(3) 0.3378(4) 0.47444(5) 0.0627(7) Uani 1 1 d . . . . .
H6 H 0.444836 0.343093 0.488674 0.075 Uiso 1 1 calc R U . . .
C7 C 0.58915(19) 0.5156(2) 0.40137(4) 0.0399(4) Uani 1 1 d . . . . .
C8 C 0.33301(19) 0.9417(3) 0.30588(5) 0.0462(5) Uani 1 1 d . . . . .
H8A H 0.308662 1.056672 0.305614 0.069 Uiso 1 1 calc R U . . .
H8B H 0.276411 0.881129 0.318568 0.069 Uiso 1 1 calc R U . . .
H8C H 0.328076 0.897249 0.286309 0.069 Uiso 1 1 calc R U . . .
C10 C 0.49110(18) 0.7352(2) 0.37665(4) 0.0368(4) Uani 1 1 d . . . . .
H10 H 0.579645 0.769828 0.373418 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4411(2) 0.6646(2) 0.34862(4) 0.0418(4) Uani 1 1 d . . . . .
H11A H 0.349166 0.678527 0.348059 0.050 Uiso 1 1 calc R U . . .
H11B H 0.459222 0.546549 0.348054 0.050 Uiso 1 1 calc R U . . .
C12 C 0.4988(2) 0.7461(2) 0.32203(4) 0.0413(4) Uani 1 1 d . . . . .
H12A H 0.472230 0.684161 0.304773 0.050 Uiso 1 1 calc R U . . .
H12B H 0.590825 0.736232 0.323458 0.050 Uiso 1 1 calc R U . . .
C13 C 0.46684(17) 0.9263(2) 0.31704(4) 0.0338(4) Uani 1 1 d . . . . .
C14 C 0.48843(17) 1.0243(2) 0.34474(4) 0.0329(4) Uani 1 1 d . . . . .
H14 H 0.569305 0.988965 0.353574 0.039 Uiso 1 1 calc R U . . .
C16 C 0.41726(18) 0.8826(2) 0.38817(4) 0.0360(4) Uani 1 1 d . . . . .
C17 C 0.2899(2) 0.8340(3) 0.40003(5) 0.0475(5) Uani 1 1 d . . . . .
H17A H 0.241269 0.932077 0.404357 0.071 Uiso 1 1 calc R U . . .
H17B H 0.301096 0.770242 0.417700 0.071 Uiso 1 1 calc R U . . .
H17C H 0.245386 0.768440 0.385674 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4923(2) 0.9744(3) 0.41080(5) 0.0493(5) Uani 1 1 d . . . . .
H18A H 0.569205 1.016671 0.402062 0.074 Uiso 1 1 calc R U . . .
H18B H 0.513755 0.900562 0.426637 0.074 Uiso 1 1 calc R U . . .
H18C H 0.442418 1.065089 0.418261 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4939(2) 1.2054(2) 0.33931(4) 0.0418(4) Uani 1 1 d . . . . .
H19A H 0.509907 1.263971 0.357598 0.050 Uiso 1 1 calc R U . . .
H19B H 0.413260 1.243824 0.331335 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5992(2) 1.2384(3) 0.31792(5) 0.0477(5) Uani 1 1 d . . . . .
H20A H 0.602659 1.356445 0.313757 0.057 Uiso 1 1 calc R U . . .
H20B H 0.679886 1.206392 0.326697 0.057 Uiso 1 1 calc R U . . .
C21 C 0.58118(19) 1.1455(2) 0.28982(5) 0.0414(4) Uani 1 1 d . . . . .
C23 C 0.7036(2) 1.1405(3) 0.27292(6) 0.0556(6) Uani 1 1 d . . . . .
H23A H 0.767387 1.083789 0.284287 0.083 Uiso 1 1 calc R U . . .
H23B H 0.731568 1.251801 0.268920 0.083 Uiso 1 1 calc R U . . .
H23C H 0.690485 1.082654 0.254686 0.083 Uiso 1 1 calc R U . . .
C24 C 0.4805(2) 1.2215(3) 0.27086(5) 0.0599(6) Uani 1 1 d . . . . .
H24A H 0.460448 1.147272 0.254980 0.090 Uiso 1 1 calc R U . . .
H24B H 0.511038 1.324831 0.263023 0.090 Uiso 1 1 calc R U . . .
H24C H 0.405190 1.241168 0.282394 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.898(2) . ?
O8 C7 1.203(3) . ?
O9 C7 1.342(2) . ?
O9 C10 1.466(2) . ?
O15 C14 1.434(2) . ?
O15 C16 1.436(2) . ?
O22 C13 1.444(2) . ?
O22 C21 1.450(2) . ?
C1 C2 1.363(4) . ?
C1 C6 1.370(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 C5 1.380(3) . ?
C4 C7 1.489(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C13 1.527(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.520(3) . ?
C10 C16 1.541(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.533(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.537(3) . ?
C13 C14 1.534(2) . ?
C14 H14 1.0000 . ?
C14 C19 1.511(3) . ?
C16 C17 1.522(3) . ?
C16 C18 1.522(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.525(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.522(3) . ?
C21 C23 1.527(3) . ?
C21 C24 1.524(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C7 O9 C10 115.93(15) . . ?
C14 O15 C16 117.07(14) . . ?
C13 O22 C21 120.89(14) . . ?
C2 C1 Br1 118.79(18) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 Br1 119.32(19) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 117.59(19) . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 C7 123.16(19) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O8 C7 O9 124.23(19) . . ?
O8 C7 C4 123.48(19) . . ?
O9 C7 C4 112.25(17) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C8 H8A 109.5 . . ?
C13 C8 H8B 109.5 . . ?
C13 C8 H8C 109.5 . . ?
O9 C10 H10 108.3 . . ?
O9 C10 C11 111.56(15) . . ?
O9 C10 C16 105.68(15) . . ?
C11 C10 H10 108.3 . . ?
C11 C10 C16 114.57(16) . . ?
C16 C10 H10 108.3 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.31(16) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C11 C12 C13 116.90(16) . . ?
H12A C12 H12B 107.3 . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
O22 C13 C8 111.86(15) . . ?
O22 C13 C12 102.80(14) . . ?
O22 C13 C14 109.27(14) . . ?
C8 C13 C12 109.83(16) . . ?
C8 C13 C14 112.42(16) . . ?
C14 C13 C12 110.26(15) . . ?
O15 C14 C13 108.65(14) . . ?
O15 C14 H14 108.7 . . ?
O15 C14 C19 109.42(15) . . ?
C13 C14 H14 108.7 . . ?
C19 C14 C13 112.55(16) . . ?
C19 C14 H14 108.7 . . ?
O15 C16 C10 108.88(15) . . ?
O15 C16 C17 104.35(16) . . ?
O15 C16 C18 109.52(16) . . ?
C17 C16 C10 112.19(16) . . ?
C18 C16 C10 111.00(17) . . ?
C18 C16 C17 110.66(17) . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 110.1 . . ?
C14 C19 H19B 110.1 . . ?
C14 C19 C20 108.19(16) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 112.00(17) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
O22 C21 C20 110.38(16) . . ?
O22 C21 C23 102.68(17) . . ?
O22 C21 C24 112.25(19) . . ?
C20 C21 C23 110.18(19) . . ?
C20 C21 C24 112.21(19) . . ?
C24 C21 C23 108.71(19) . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
Br1 C1 C2 C3 -177.54(19) . . . . ?
Br1 C1 C6 C5 176.9(2) . . . . ?
O9 C10 C11 C12 -151.08(16) . . . . ?
O9 C10 C16 O15 -166.41(14) . . . . ?
O9 C10 C16 C17 -51.4(2) . . . . ?
O9 C10 C16 C18 72.96(19) . . . . ?
O15 C14 C19 C20 -179.27(16) . . . . ?
O22 C13 C14 O15 173.05(13) . . . . ?
O22 C13 C14 C19 51.7(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C2 C3 C4 C7 174.0(2) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C3 C4 C7 O8 1.8(3) . . . . ?
C3 C4 C7 O9 -176.10(19) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C5 C4 C7 O8 178.4(2) . . . . ?
C5 C4 C7 O9 0.5(3) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C7 O9 C10 C11 85.2(2) . . . . ?
C7 O9 C10 C16 -149.68(16) . . . . ?
C7 C4 C5 C6 -174.5(2) . . . . ?
C8 C13 C14 O15 48.2(2) . . . . ?
C8 C13 C14 C19 -73.1(2) . . . . ?
C10 O9 C7 O8 -7.0(3) . . . . ?
C10 O9 C7 C4 170.85(16) . . . . ?
C10 C11 C12 C13 -66.2(2) . . . . ?
C11 C10 C16 O15 -43.2(2) . . . . ?
C11 C10 C16 C17 71.8(2) . . . . ?
C11 C10 C16 C18 -163.80(17) . . . . ?
C11 C12 C13 O22 166.13(17) . . . . ?
C11 C12 C13 C8 -74.7(2) . . . . ?
C11 C12 C13 C14 49.7(2) . . . . ?
C12 C13 C14 O15 -74.66(18) . . . . ?
C12 C13 C14 C19 164.00(16) . . . . ?
C13 O22 C21 C20 47.4(2) . . . . ?
C13 O22 C21 C23 164.87(17) . . . . ?
C13 O22 C21 C24 -78.6(2) . . . . ?
C13 C14 C19 C20 -58.4(2) . . . . ?
C14 O15 C16 C10 -45.4(2) . . . . ?
C14 O15 C16 C17 -165.34(15) . . . . ?
C14 O15 C16 C18 76.2(2) . . . . ?
C14 C19 C20 C21 57.5(2) . . . . ?
C16 O15 C14 C13 104.01(17) . . . . ?
C16 O15 C14 C19 -132.75(17) . . . . ?
C16 C10 C11 C12 88.9(2) . . . . ?
C19 C20 C21 O22 -50.5(2) . . . . ?
C19 C20 C21 C23 -163.23(18) . . . . ?
C19 C20 C21 C24 75.5(2) . . . . ?
C21 O22 C13 C8 77.7(2) . . . . ?
C21 O22 C13 C12 -164.51(16) . . . . ?
C21 O22 C13 C14 -47.4(2) . . . . ?

_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 1.616
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# 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_trans_syn-(BA)-3
_database_code_depnum_ccdc_archive 'CCDC 2176607'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H29 Br O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   6.41587(11)
_cell_length_b                   12.0405(3)
_cell_length_c                   13.3039(3)
_cell_angle_alpha                94.139(2)
_cell_angle_beta                 91.6023(17)
_cell_angle_gamma                101.2879(17)
_cell_volume                     1004.29(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      73.1740
_cell_measurement_theta_min      3.3250
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.459
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0206
0 -1 0 0.0206
1 0 0 0.1469
-1 0 0 0.1469
0 0 1 0.0130
0 0 -1 0.0130

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
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
-0.0001 1.0007 -0.0002 -0.0189 0.1295 0.0036
0.0001 -1.0007 0.0002 0.0189 -0.1295 -0.0036
1.0005 0.0010 0.0006 -0.0370 0.0372 0.2395
-1.0005 -0.0010 -0.0006 0.0370 -0.0372 -0.2395
0.0001 0.0003 1.0004 -0.1155 -0.0072 -0.0115
-0.0001 -0.0003 -1.0004 0.1155 0.0072 0.0115

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.508
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -27.00   0.50    0.50    --  -57.30 -15.00-150.00  150
  2  ω    -87.00 -36.00   0.50    0.50    --  -57.30   0.00-180.00  102
  3  ω    -96.00 -18.00   0.50    0.50    --  -57.30   0.00 -90.00  156
  4  ω     28.00  56.00   0.50    0.50    --   60.47  15.00  90.00   56
  5  ω     42.00  90.00   0.50    0.50    --   60.47-125.00  90.00   96
  6  ω     22.00  69.00   0.50    0.50    --   60.47 -94.00-120.00   94
  7  ω     22.00  47.00   0.50    0.50    --   60.47 -94.00-180.00   50
  8  ω     62.00 100.00   0.50    0.50    --   60.47  15.00  90.00   76
  9  ω     70.00  99.00   0.50    0.50    --   60.47  15.00-180.00   58
 10  ω     22.00  70.00   0.50    0.50    --   60.47 -94.00 120.00   96
 11  ω     26.00  69.00   0.50    0.50    --   60.47 -94.00 -60.00   86
 12  ω     44.00  71.00   0.50    0.50    --   75.00 -94.00 120.00   54
 13  ω     35.00  69.00   0.50    0.50    --   75.00 -94.00-180.00   68
 14  ω     41.00  67.00   0.50    0.50    --   75.00-125.00 -30.00   52
 15  ω     36.00  80.00   0.50    0.50    --   75.00 -94.00  30.00   88
 16  ω     35.00  60.00   0.50    0.50    --   75.00 -94.00 150.00   50
 17  ω     44.00  70.00   0.50    0.50    --   75.00 -94.00 -30.00   52
 18  ω     38.00  67.00   0.50    0.50    --   77.04 -94.00  60.00   58
 19  ω     45.00  97.00   0.50    0.50    --   77.04  15.00-150.00  104
 20  ω     38.00  86.00   0.50    0.50    --   77.04 -94.00-120.00   96
 21  ω     39.00  65.00   0.50    0.50    --   77.04-125.00  60.00   52
 22  ω     72.00  98.00   0.50    0.50    --   77.04-125.00 150.00   52
 23  ω     36.00  62.00   0.50    0.50    --   77.04-125.00 150.00   52
 24  ω     83.00 108.00   0.50    0.50    --   77.04-125.00-120.00   50
 25  ω     56.00  81.00   0.50    0.50    --   77.04-122.00 142.00   50
 26  ω     77.00 106.00   0.50    0.50    --   77.04-125.00  60.00   58
 27  ω     35.00  60.00   0.50    0.50    --   77.04-125.00 -60.00   50
 28  ω     37.00  62.00   0.50    0.50    --   77.04 -94.00 -30.00   50
 29  ω     58.00  86.00   0.50    0.50    --   77.04 -94.00 -60.00   56
 30  ω     40.00  87.00   0.50    0.50    --   77.04 -94.00 -90.00   94
 31  ω     38.00  79.00   0.50    0.50    --   77.04   0.00-150.00   82
 32  ω     38.00  64.00   0.50    0.50    --   77.04 -94.00 120.00   52
 33  ω     50.00 119.00   0.50    0.50    --   77.04  15.00  30.00  138
 34  ω     55.00  80.00   0.50    0.50    --   77.04 -94.00   0.00   50
 35  ω     76.00 102.00   0.50    0.50    --   77.04-150.00 -19.00   52
 36  ω     50.00 106.00   0.50    0.50    --   77.04-125.00 120.00  112
 37  ω     62.00  87.00   0.50    0.50    --   77.04 -94.00-180.00   50
 38  ω     84.00 117.00   0.50    0.50    --   77.04   0.00-120.00   66
 39  ω     48.00  74.00   0.50    0.50    --   77.04 -94.00-150.00   52
 40  ω     65.00 119.00   0.50    0.50    --   77.04  15.00 -90.00  108
 41  ω     47.00 123.00   0.50    0.50    --   77.04  15.00 120.00  152
 42  ω     38.00  63.00   0.50    0.50    --   81.25 -55.00 139.97   50
 43  ω     47.00  88.00   0.50    0.50    --   81.25-105.00 167.91   82
 44  ω     86.00 115.00   0.50    0.50    --   81.25-133.00  25.84   58
 45  ω     40.00  82.00   0.50    0.50    --   81.25-133.00  25.84   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369097000
_diffrn_orient_matrix_UB_12      -0.0188754000
_diffrn_orient_matrix_UB_13      -0.1154079000
_diffrn_orient_matrix_UB_21      0.0370821000
_diffrn_orient_matrix_UB_22      0.1294649000
_diffrn_orient_matrix_UB_23      -0.0071980000
_diffrn_orient_matrix_UB_31      0.2394309000
_diffrn_orient_matrix_UB_32      0.0036129000
_diffrn_orient_matrix_UB_33      -0.0115575000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3516
_reflns_number_total             3964
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+1.0210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0986
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.72010(5) 1.09426(2) 0.25157(2) 0.03414(11) Uani 1 1 d . . . . .
O1 O 1.0743(3) 0.71083(16) 0.53412(14) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.7320(3) 0.68503(15) 0.57879(13) 0.0260(4) Uani 1 1 d . . . . .
O3 O 0.6780(3) 0.54032(14) 0.81177(12) 0.0219(3) Uani 1 1 d . . . . .
O4 O 0.8277(3) 0.27220(15) 0.84532(13) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.7713(4) 0.9826(2) 0.33690(18) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.6116(4) 0.9337(2) 0.3973(2) 0.0283(5) Uani 1 1 d . . . . .
H2 H 0.477868 0.956362 0.395962 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6481(4) 0.8517(2) 0.45964(19) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.539388 0.817506 0.501147 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8452(4) 0.8195(2) 0.46114(17) 0.0220(5) Uani 1 1 d . . . . .
C5 C 1.0033(4) 0.8695(2) 0.39960(19) 0.0260(5) Uani 1 1 d . . . . .
H5 H 1.137366 0.847152 0.400753 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9678(4) 0.9509(2) 0.3371(2) 0.0289(5) Uani 1 1 d . . . . .
H6 H 1.075751 0.984582 0.294968 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8995(4) 0.7336(2) 0.52738(18) 0.0234(5) Uani 1 1 d . . . . .
C8 C 0.7752(4) 0.6058(2) 0.65106(18) 0.0241(5) Uani 1 1 d . . . . .
H8 H 0.927269 0.628624 0.675855 0.029 Uiso 1 1 calc R U . . .
C9 C 0.7386(4) 0.4855(2) 0.60277(19) 0.0273(5) Uani 1 1 d . . . . .
H9A H 0.830360 0.481381 0.544575 0.033 Uiso 1 1 calc R U . . .
H9B H 0.588261 0.460355 0.578546 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7933(4) 0.4100(2) 0.68311(18) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.948260 0.429566 0.699481 0.031 Uiso 1 1 calc R U . . .
H10B H 0.758514 0.329709 0.655265 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6739(4) 0.4221(2) 0.78034(18) 0.0215(5) Uani 1 1 d . . . . .
C12 C 0.6330(4) 0.6176(2) 0.73999(18) 0.0224(5) Uani 1 1 d . . . . .
C13 C 0.7015(4) 0.7344(2) 0.7972(2) 0.0270(5) Uani 1 1 d . . . . .
H13A H 0.613748 0.739293 0.855807 0.040 Uiso 1 1 calc R U . . .
H13B H 0.683500 0.793432 0.752567 0.040 Uiso 1 1 calc R U . . .
H13C H 0.851348 0.745302 0.819810 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3964(4) 0.5984(2) 0.70835(19) 0.0257(5) Uani 1 1 d . . . . .
H14A H 0.355532 0.526408 0.666710 0.039 Uiso 1 1 calc R U . . .
H14B H 0.370677 0.660858 0.669482 0.039 Uiso 1 1 calc R U . . .
H14C H 0.311728 0.595599 0.768618 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4468(4) 0.3521(2) 0.7697(2) 0.0280(5) Uani 1 1 d . . . . .
H15A H 0.359868 0.381199 0.820893 0.042 Uiso 1 1 calc R U . . .
H15B H 0.449302 0.272399 0.779131 0.042 Uiso 1 1 calc R U . . .
H15C H 0.385946 0.357951 0.702394 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8014(4) 0.3870(2) 0.86800(18) 0.0226(5) Uani 1 1 d . . . . .
H16 H 0.945544 0.437444 0.873112 0.027 Uiso 1 1 calc R U . . .
C17 C 0.7088(4) 0.3886(2) 0.97192(18) 0.0258(5) Uani 1 1 d . . . . .
H17A H 0.553248 0.359076 0.968309 0.031 Uiso 1 1 calc R U . . .
H17B H 0.739565 0.465829 1.006767 0.031 Uiso 1 1 calc R U . . .
C18 C 0.8286(4) 0.3086(2) 1.02308(19) 0.0270(5) Uani 1 1 d . . . . .
H18A H 0.748920 0.274729 1.079751 0.032 Uiso 1 1 calc R U . . .
H18B H 0.971699 0.349031 1.048716 0.032 Uiso 1 1 calc R U . . .
C19 C 0.8439(4) 0.2172(2) 0.93817(18) 0.0242(5) Uani 1 1 d . . . . .
C20 C 0.6596(5) 0.1160(3) 0.9356(2) 0.0384(7) Uani 1 1 d . . . . .
H20A H 0.673039 0.072923 0.994380 0.058 Uiso 1 1 calc R U . . .
H20B H 0.661843 0.066903 0.873741 0.058 Uiso 1 1 calc R U . . .
H20C H 0.524995 0.142911 0.936984 0.058 Uiso 1 1 calc R U . . .
C21 C 1.0547(4) 0.1779(2) 0.9415(2) 0.0315(6) Uani 1 1 d . . . . .
H21A H 1.061662 0.125976 0.882089 0.047 Uiso 1 1 calc R U . . .
H21B H 1.066661 0.138562 1.002752 0.047 Uiso 1 1 calc R U . . .
H21C H 1.171712 0.243888 0.941939 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.891(2) . ?
O1 C7 1.208(3) . ?
O2 C7 1.349(3) . ?
O2 C8 1.461(3) . ?
O3 C11 1.449(3) . ?
O3 C12 1.442(3) . ?
O4 C16 1.437(3) . ?
O4 C19 1.454(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.387(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.491(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.512(4) . ?
C8 C12 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.534(3) . ?
C11 C15 1.531(3) . ?
C11 C16 1.536(3) . ?
C12 C13 1.527(3) . ?
C12 C14 1.532(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.520(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.529(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.538(4) . ?
C19 C20 1.521(4) . ?
C19 C21 1.518(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C7 O2 C8 115.89(18) . . ?
C12 O3 C11 120.72(17) . . ?
C16 O4 C19 109.99(17) . . ?
C2 C1 Br1 119.41(19) . . ?
C2 C1 C6 121.4(2) . . ?
C6 C1 Br1 119.15(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C7 123.2(2) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 C7 117.0(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 H6 120.7 . . ?
O1 C7 O2 124.1(2) . . ?
O1 C7 C4 123.5(2) . . ?
O2 C7 C4 112.3(2) . . ?
O2 C8 H8 108.7 . . ?
O2 C8 C9 111.3(2) . . ?
O2 C8 C12 107.09(19) . . ?
C9 C8 H8 108.7 . . ?
C9 C8 C12 112.4(2) . . ?
C12 C8 H8 108.7 . . ?
C8 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
C8 C9 C10 107.3(2) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 113.0(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
O3 C11 C10 111.44(19) . . ?
O3 C11 C15 111.94(19) . . ?
O3 C11 C16 101.30(18) . . ?
C10 C11 C16 108.72(19) . . ?
C15 C11 C10 111.4(2) . . ?
C15 C11 C16 111.6(2) . . ?
O3 C12 C8 106.97(19) . . ?
O3 C12 C13 103.61(19) . . ?
O3 C12 C14 112.79(19) . . ?
C8 C12 C14 113.1(2) . . ?
C13 C12 C8 110.4(2) . . ?
C13 C12 C14 109.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C11 108.89(19) . . ?
O4 C16 H16 108.1 . . ?
O4 C16 C17 105.36(19) . . ?
C11 C16 H16 108.1 . . ?
C17 C16 C11 117.9(2) . . ?
C17 C16 H16 108.1 . . ?
C16 C17 H17A 111.6 . . ?
C16 C17 H17B 111.6 . . ?
C16 C17 C18 100.6(2) . . ?
H17A C17 H17B 109.4 . . ?
C18 C17 H17A 111.6 . . ?
C18 C17 H17B 111.6 . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
C17 C18 C19 103.5(2) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
O4 C19 C18 104.97(19) . . ?
O4 C19 C20 107.4(2) . . ?
O4 C19 C21 108.3(2) . . ?
C20 C19 C18 112.4(2) . . ?
C21 C19 C18 113.0(2) . . ?
C21 C19 C20 110.4(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Br1 C1 C2 C3 179.8(2) . . . . ?
Br1 C1 C6 C5 180.0(2) . . . . ?
O2 C8 C9 C10 178.55(19) . . . . ?
O2 C8 C12 O3 -179.30(18) . . . . ?
O2 C8 C12 C13 -67.2(2) . . . . ?
O2 C8 C12 C14 55.9(3) . . . . ?
O3 C11 C16 O4 -175.58(17) . . . . ?
O3 C11 C16 C17 64.5(2) . . . . ?
O4 C16 C17 C18 37.4(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C7 178.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C7 O1 -174.8(2) . . . . ?
C3 C4 C7 O2 4.9(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C5 C4 C7 O1 4.3(4) . . . . ?
C5 C4 C7 O2 -175.9(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C7 O2 C8 C9 -91.2(2) . . . . ?
C7 O2 C8 C12 145.6(2) . . . . ?
C7 C4 C5 C6 -179.0(2) . . . . ?
C8 O2 C7 O1 4.1(4) . . . . ?
C8 O2 C7 C4 -175.7(2) . . . . ?
C8 C9 C10 C11 53.7(3) . . . . ?
C9 C8 C12 O3 58.2(2) . . . . ?
C9 C8 C12 C13 170.3(2) . . . . ?
C9 C8 C12 C14 -66.6(3) . . . . ?
C9 C10 C11 O3 -45.2(3) . . . . ?
C9 C10 C11 C15 80.5(3) . . . . ?
C9 C10 C11 C16 -156.1(2) . . . . ?
C10 C11 C16 O4 -58.1(2) . . . . ?
C10 C11 C16 C17 -178.0(2) . . . . ?
C11 O3 C12 C8 -51.2(3) . . . . ?
C11 O3 C12 C13 -167.88(19) . . . . ?
C11 O3 C12 C14 73.8(3) . . . . ?
C11 C16 C17 C18 159.2(2) . . . . ?
C12 O3 C11 C10 46.0(3) . . . . ?
C12 O3 C11 C15 -79.5(2) . . . . ?
C12 O3 C11 C16 161.43(18) . . . . ?
C12 C8 C9 C10 -61.3(3) . . . . ?
C15 C11 C16 O4 65.1(2) . . . . ?
C15 C11 C16 C17 -54.8(3) . . . . ?
C16 O4 C19 C18 -0.8(2) . . . . ?
C16 O4 C19 C20 119.1(2) . . . . ?
C16 O4 C19 C21 -121.7(2) . . . . ?
C16 C17 C18 C19 -37.2(2) . . . . ?
C17 C18 C19 O4 24.4(2) . . . . ?
C17 C18 C19 C20 -92.1(2) . . . . ?
C17 C18 C19 C21 142.1(2) . . . . ?
C19 O4 C16 C11 -150.89(19) . . . . ?
C19 O4 C16 C17 -23.5(2) . . . . ?

_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.748
####################################################################### 
# 
# 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_trans_anti-(AA)-5
_database_code_depnum_ccdc_archive 'CCDC 2176603'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 O3'
_chemical_formula_sum            'C14 H26 O3'
_chemical_formula_weight         242.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H26 O3'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.8614(2)
_cell_length_b                   15.5412(7)
_cell_length_c                   14.8746(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.764(4)
_cell_angle_gamma                90
_cell_volume                     1354.85(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      73.9720
_cell_measurement_theta_min      4.0830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0219
-1 0 -1 0.0084
0 0 -1 0.0010
0 2 -1 0.0010
0 -2 1 0.0244
1 0 -3 0.0255

_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.023
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
0.0002 -0.0005 1.0011 0.0980 0.0336 -0.0006
-1.0013 0.0013 -1.0013 -0.0988 -0.0472 -0.2623
-0.0002 0.0005 -1.0011 -0.0980 -0.0336 0.0006
0.0007 2.0025 -1.0006 -0.0337 -0.2211 0.0104
-0.0007 -2.0025 1.0006 0.0337 0.2211 -0.0104
1.0007 0.0007 -3.0031 -0.2934 -0.0873 0.2647

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18499
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.876
_diffrn_reflns_theta_min         4.114
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -26.00   0.50   15.00    --  -57.30 -15.00-120.00   72
  2  ω    -81.00 -55.00   0.50   15.00    --  -57.30   0.00 -90.00   52
  3  ω    -65.00 -38.00   0.50   15.00    --  -57.30 125.00-120.00   54
  4  ω    -84.00 -20.00   0.50   15.00    --  -57.30   0.00 -60.00  128
  5  ω    -78.00 -52.00   0.50   15.00    --  -57.30 -15.00   0.00   52
  6  ω    -97.00 -40.00   0.50   15.00    --  -57.30   0.00  30.00  114
  7  ω     22.00  53.00   0.50   15.00    --   60.47 -94.00 120.00   62
  8  ω     31.00  62.00   0.50   15.00    --   60.47 -94.00 -30.00   62
  9  ω     25.00  57.00   0.50   15.00    --   60.47 -94.00  60.00   64
 10  ω     21.00  66.00   0.50   15.00    --   60.47 -94.00-180.00   90
 11  ω     25.00  62.00   0.50   15.00    --   60.47 -94.00-120.00   74
 12  ω     40.00  83.00   0.50   15.00    --   75.00 -94.00 120.00   86
 13  ω     47.00  73.00   0.50   15.00    --   75.00  15.00-120.00   52
 14  ω     36.00  64.00   0.50   15.00    --   75.00 -94.00 150.00   56
 15  ω     43.00  69.00   0.50   15.00    --   75.00-127.00  70.00   52
 16  ω     79.00 105.00   0.50   15.00    --   75.00-127.00  70.00   52
 17  ω     92.00 118.00   0.50   15.00    --   75.00  15.00-120.00   52
 18  ω     44.00  87.00   0.50   15.00    --   77.04 -94.00 -60.00   86
 19  ω     38.00  66.00   0.50   15.00    --   77.04 -94.00-180.00   56
 20  ω     39.00  89.00   0.50   15.00    --   77.04   0.00 150.00  100
 21  ω     76.00 107.00   0.50   15.00    --   77.04-125.00 -90.00   62
 22  ω     38.00  63.00   0.50   15.00    --   77.04-125.00 -90.00   50
 23  ω     93.00 123.00   0.50   15.00    --   77.04  15.00  60.00   60
 24  ω     41.00  86.00   0.50   15.00    --   77.04 -94.00  30.00   90
 25  ω     45.00  84.00   0.50   15.00    --   77.04 -94.00-150.00   78
 26  ω     54.00 121.00   0.50   15.00    --   77.04  15.00 -30.00  134
 27  ω     54.00  81.00   0.50   15.00    --   77.04-125.00   0.00   54
 28  ω     41.00 112.00   0.50   15.00    --   77.04   0.00-120.00  142
 29  ω     36.00  76.00   0.50   15.00    --   77.04-125.00  90.00   80
 30  ω     56.00  97.00   0.50   15.00    --   77.04  15.00  30.00   82
 31  ω     41.00  82.00   0.50   15.00    --   77.04 -94.00 -30.00   82
 32  ω     42.00  67.00   0.50   15.00    --   77.04 -94.00 -90.00   50
 33  ω     36.00  71.00   0.50   15.00    --   81.25-112.00  97.01   70
 34  ω     36.00 108.00   0.50   15.00    --   81.25-116.00  32.13  144
 35  ω     72.00 110.00   0.50   15.00    --   81.25-124.00-172.77   76
 36  ω     97.00 125.00   0.50   15.00    --   81.25-167.00  -8.65   56
 37  ω     66.00  92.00   0.50   15.00    --   81.25-167.00  -8.65   52
 38  ω     77.00 114.00   0.50   15.00    --   81.25-128.00-129.64   74
 39  ω     46.00  75.00   0.50   15.00    --   81.25 -75.00-149.92   58
 40  ω     68.00 127.00   0.50   15.00    --   81.25  18.00 149.82  118
 41  ω     76.00 104.00   0.50   15.00    --   81.25-112.00  97.01   56
 42  ω     40.00  65.00   0.50   15.00    --   81.25-128.00-129.64   50
 43  ω     36.00  67.00   0.50   15.00    --   81.25-124.00-172.77   62
 44  ω     57.00 108.00   0.50   15.00    --   81.25-116.00 123.04  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0007402000
_diffrn_orient_matrix_UB_12      0.0320978000
_diffrn_orient_matrix_UB_13      0.0979478000
_diffrn_orient_matrix_UB_21      0.0134620000
_diffrn_orient_matrix_UB_22      -0.0936420000
_diffrn_orient_matrix_UB_23      0.0335311000
_diffrn_orient_matrix_UB_31      0.2626294000
_diffrn_orient_matrix_UB_32      0.0047758000
_diffrn_orient_matrix_UB_33      -0.0006227000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2373
_reflns_number_total             2728
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.088
_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)+(0.0770P)²+0.7245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-H5
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_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
O3 O 0.1630(2) 0.67993(8) 0.57141(8) 0.0216(3) Uani 1 1 d . . . . .
O5 O 0.6841(2) 0.65654(10) 0.51045(10) 0.0288(3) Uani 1 1 d D . . . .
H5 H 0.820(3) 0.6671(17) 0.5268(18) 0.043 Uiso 1 1 d D U . . .
O8 O 0.4568(2) 0.60073(9) 0.77615(9) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.2922(3) 0.70706(13) 0.49343(12) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.1680(3) 0.78785(13) 0.46103(13) 0.0264(4) Uani 1 1 d . . . . .
H2A H 0.005202 0.775203 0.452905 0.040 Uiso 1 1 calc R U . . .
H2B H 0.231611 0.806538 0.403646 0.040 Uiso 1 1 calc R U . . .
H2C H 0.187357 0.833696 0.505718 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2791(3) 0.63752(13) 0.42150(13) 0.0276(4) Uani 1 1 d . . . . .
H3A H 0.340735 0.583579 0.445792 0.041 Uiso 1 1 calc R U . . .
H3B H 0.368537 0.655246 0.369463 0.041 Uiso 1 1 calc R U . . .
H3C H 0.119694 0.628977 0.402917 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5419(3) 0.73113(13) 0.51766(13) 0.0241(4) Uani 1 1 d . . . . .
H4 H 0.593858 0.772981 0.471156 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5686(3) 0.77578(13) 0.60928(13) 0.0256(4) Uani 1 1 d . . . . .
H6A H 0.709163 0.811059 0.608613 0.031 Uiso 1 1 calc R U . . .
H6B H 0.438176 0.815450 0.617109 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5808(3) 0.71576(13) 0.69032(13) 0.0244(4) Uani 1 1 d . . . . .
H7A H 0.623779 0.750688 0.743570 0.029 Uiso 1 1 calc R U . . .
H7B H 0.706337 0.674375 0.680317 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1921(3) 0.72300(12) 0.75714(13) 0.0247(4) Uani 1 1 d . . . . .
H8A H 0.051884 0.690548 0.768142 0.037 Uiso 1 1 calc R U . . .
H8B H 0.158186 0.771422 0.716923 0.037 Uiso 1 1 calc R U . . .
H8C H 0.253712 0.744830 0.814309 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3672(3) 0.66422(12) 0.71364(12) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.2710(3) 0.61766(12) 0.62990(12) 0.0220(4) Uani 1 1 d . . . . .
H10 H 0.400627 0.590673 0.597186 0.026 Uiso 1 1 calc R U . . .
C11 C 0.1026(3) 0.54794(12) 0.65412(13) 0.0253(4) Uani 1 1 d . . . . .
H11A H 0.045914 0.518956 0.598924 0.030 Uiso 1 1 calc R U . . .
H11B H -0.029407 0.573442 0.685282 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2226(3) 0.48288(13) 0.71553(13) 0.0261(4) Uani 1 1 d . . . . .
H12A H 0.344429 0.453716 0.681584 0.031 Uiso 1 1 calc R U . . .
H12B H 0.111337 0.438595 0.734125 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3275(3) 0.52502(12) 0.79962(13) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.1476(4) 0.54444(14) 0.87015(14) 0.0314(5) Uani 1 1 d . . . . .
H14A H 0.213926 0.581473 0.916980 0.047 Uiso 1 1 calc R U . . .
H14B H 0.095707 0.490488 0.897163 0.047 Uiso 1 1 calc R U . . .
H14C H 0.017721 0.573837 0.841551 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5093(4) 0.46626(14) 0.84093(15) 0.0328(5) Uani 1 1 d . . . . .
H15A H 0.630888 0.456844 0.797408 0.049 Uiso 1 1 calc R U . . .
H15B H 0.440366 0.410935 0.856732 0.049 Uiso 1 1 calc R U . . .
H15C H 0.573492 0.493269 0.895165 0.049 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 C1 1.456(2) . ?
O3 C10 1.442(2) . ?
O5 H5 0.845(17) . ?
O5 C4 1.432(2) . ?
O8 C9 1.449(2) . ?
O8 C13 1.445(2) . ?
C1 C2 1.526(3) . ?
C1 C3 1.522(3) . ?
C1 C4 1.549(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 1.0000 . ?
C4 C6 1.535(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C9 1.530(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.525(3) . ?
C9 C10 1.541(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.512(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.533(3) . ?
C13 C14 1.527(3) . ?
C13 C15 1.527(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 C1 116.52(13) . . ?
C4 O5 H5 111.6(19) . . ?
C13 O8 C9 121.49(14) . . ?
O3 C1 C2 103.83(14) . . ?
O3 C1 C3 109.43(15) . . ?
O3 C1 C4 112.61(14) . . ?
C2 C1 C4 108.67(15) . . ?
C3 C1 C2 110.04(15) . . ?
C3 C1 C4 111.94(15) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C4 C1 109.63(15) . . ?
O5 C4 H4 107.0 . . ?
O5 C4 C6 112.32(15) . . ?
C1 C4 H4 107.0 . . ?
C6 C4 C1 113.60(15) . . ?
C6 C4 H4 107.0 . . ?
C4 C6 H6A 108.4 . . ?
C4 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C4 115.36(16) . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 H7A 107.8 . . ?
C6 C7 H7B 107.8 . . ?
C6 C7 C9 117.99(15) . . ?
H7A C7 H7B 107.1 . . ?
C9 C7 H7A 107.8 . . ?
C9 C7 H7B 107.8 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
O8 C9 C7 102.20(14) . . ?
O8 C9 C8 112.08(15) . . ?
O8 C9 C10 108.93(14) . . ?
C7 C9 C10 110.76(15) . . ?
C8 C9 C7 109.88(15) . . ?
C8 C9 C10 112.53(15) . . ?
O3 C10 C9 109.00(15) . . ?
O3 C10 H10 108.5 . . ?
O3 C10 C11 110.00(14) . . ?
C9 C10 H10 108.5 . . ?
C11 C10 C9 112.14(15) . . ?
C11 C10 H10 108.5 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
C10 C11 C12 108.65(15) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.42(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
O8 C13 C12 110.90(15) . . ?
O8 C13 C14 111.98(16) . . ?
O8 C13 C15 102.62(15) . . ?
C14 C13 C12 111.82(16) . . ?
C15 C13 C12 110.07(17) . . ?
C15 C13 C14 109.06(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C1 C4 O5 90.35(18) . . . . ?
O3 C1 C4 C6 -36.2(2) . . . . ?
O3 C10 C11 C12 179.65(15) . . . . ?
O5 C4 C6 C7 -42.2(2) . . . . ?
O8 C9 C10 O3 174.76(13) . . . . ?
O8 C9 C10 C11 52.72(19) . . . . ?
C1 O3 C10 C9 101.87(17) . . . . ?
C1 O3 C10 C11 -134.80(16) . . . . ?
C1 C4 C6 C7 83.0(2) . . . . ?
C2 C1 C4 O5 -155.20(16) . . . . ?
C2 C1 C4 C6 78.22(19) . . . . ?
C3 C1 C4 O5 -33.4(2) . . . . ?
C3 C1 C4 C6 -160.03(16) . . . . ?
C4 C6 C7 C9 -67.1(2) . . . . ?
C6 C7 C9 O8 165.89(16) . . . . ?
C6 C7 C9 C8 -75.0(2) . . . . ?
C6 C7 C9 C10 50.0(2) . . . . ?
C7 C9 C10 O3 -73.59(18) . . . . ?
C7 C9 C10 C11 164.36(15) . . . . ?
C8 C9 C10 O3 49.8(2) . . . . ?
C8 C9 C10 C11 -72.21(19) . . . . ?
C9 O8 C13 C12 45.7(2) . . . . ?
C9 O8 C13 C14 -80.0(2) . . . . ?
C9 O8 C13 C15 163.16(16) . . . . ?
C9 C10 C11 C12 -58.9(2) . . . . ?
C10 O3 C1 C2 -165.08(14) . . . . ?
C10 O3 C1 C3 77.46(18) . . . . ?
C10 O3 C1 C4 -47.7(2) . . . . ?
C10 C11 C12 C13 56.0(2) . . . . ?
C11 C12 C13 O8 -47.8(2) . . . . ?
C11 C12 C13 C14 78.0(2) . . . . ?
C11 C12 C13 C15 -160.62(17) . . . . ?
C13 O8 C9 C7 -164.80(15) . . . . ?
C13 O8 C9 C8 77.6(2) . . . . ?
C13 O8 C9 C10 -47.6(2) . . . . ?

_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 2.044
_oxdiff_exptl_absorpt_empirical_full_min 0.532
####################################################################### 
# 
# 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_cis_anti-(AB)-4
_database_code_depnum_ccdc_archive 'CCDC 2176606'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H29 Br O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   14.0432(5)
_cell_length_b                   7.0309(3)
_cell_length_c                   21.1186(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.447(4)
_cell_angle_gamma                90
_cell_volume                     2050.61(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19361
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      3.1480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -1 0.0075
-2 0 1 0.0187
0 0 1 0.0068
0 0 -1 0.0235
0 -1 0 0.2102
0 1 0 0.2406

_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.026
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
2.0073 -0.0011 -1.0036 0.1798 -0.1315 0.0065
-2.0073 0.0011 1.0036 -0.1798 0.1315 -0.0065
0.0021 0.0007 1.0001 0.0281 0.0590 0.0352
-0.0021 -0.0007 -1.0001 -0.0281 -0.0590 -0.0352
-0.0062 -1.0010 0.0046 -0.0677 -0.0822 0.1917
0.0062 1.0010 -0.0046 0.0677 0.0822 -0.1917

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.569
_diffrn_reflns_theta_min         3.200
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  29.00   0.50    4.00    --    2.00  33.00 -67.11   50
  2  ω      5.00  31.00   0.50    4.00    --    2.00  33.00 -38.79   52
  3  ω      8.00  33.00   0.50    4.00    --   10.00  30.00 -78.05   50
  4  ω     15.00  41.00   0.50    4.00    --   22.00  27.00 -42.80   52
  5  ω     13.00  40.00   0.50    4.00    --   22.00  27.00   0.06   54
  6  ω    -48.00 -23.00   0.50    4.00    --  -34.00 -26.00 148.13   50
  7  ω    -50.00 -24.00   0.50    4.00    --  -42.00 -25.00  95.04   52
  8  ω    -51.00 -26.00   0.50    4.00    --  -42.00 -25.00-179.85   50
  9  ω    -56.00 -30.00   0.50    4.00    --  -50.00 -24.00 126.84   52
 10  ω    -56.00 -30.00   0.50    4.00    --  -50.00 -24.00-154.30   52
 11  ω    -61.00 -36.00   0.50    4.00    --  -58.00 -23.00-178.30   50
 12  ω   -100.00 -75.00   0.50    4.00    --  -59.37   0.00  60.00   50
 13  ω    -92.00 -54.00   0.50    4.00    --  -59.37   0.00 150.00   76
 14  ω    -50.00 -18.00   0.50    4.00    --  -59.37   0.00 150.00   64
 15  ω    -98.00 -32.00   0.50    4.00    --  -59.37 -15.00 -90.00  132
 16  ω     36.00  62.00   0.50    4.00    --   59.80 -94.00-120.00   52
 17  ω     21.00  72.00   0.50    4.00    --   59.80 -94.00  90.00  102
 18  ω     19.00  67.00   0.50    4.00    --   59.80 -94.00  30.00   96
 19  ω     24.00  69.00   0.50    4.00    --   59.80 -94.00 150.00   90
 20  ω     38.00  66.00   0.50    4.00    --   59.80 -94.00 -30.00   56
 21  ω    -88.00 -62.00   0.50    4.00    --  -66.50 -18.00 124.96   52
 22  ω    -70.00 -45.00   0.50    4.00    --  -66.50 -22.00  92.99   50
 23  ω     93.00 118.00   0.50    4.00    --   66.78  21.00 -78.76   50
 24  ω     41.00  67.00   0.50    4.00    --   66.78  22.00 -44.85   52
 25  ω     56.00  81.00   0.50    4.00    --   76.98 -94.00 -30.00   50
 26  ω     35.00  77.00   0.50    4.00    --   76.98-125.00   0.00   84
 27  ω     85.00 110.00   0.50    4.00    --   76.98-125.00  30.00   50
 28  ω     36.00  88.00   0.50    4.00    --   76.98 -94.00  90.00  104
 29  ω     35.00  76.00   0.50    4.00    --   76.98   0.00  30.00   82
 30  ω     79.00 104.00   0.50    4.00    --   76.98   0.00  30.00   50
 31  ω     80.00 105.00   0.50    4.00    --   76.98-125.00 120.00   50
 32  ω     35.00  61.00   0.50    4.00    --   76.98-125.00 120.00   52
 33  ω     35.00  76.00   0.50    4.00    --   76.98-125.00-180.00   82
 34  ω     65.00  91.00   0.50    4.00    --   76.98-125.00 150.00   52
 35  ω     38.00  63.00   0.50    4.00    --   76.98-125.00 150.00   50
 36  ω     38.00  77.00   0.50    4.00    --   76.98 -94.00 -90.00   78
 37  ω     40.00  87.00   0.50    4.00    --   76.98 -94.00   0.00   94
 38  ω     39.00  87.00   0.50    4.00    --   76.98-125.00  60.00   96
 39  ω     35.00  62.00   0.50    4.00    --   76.98-125.00  90.00   54
 40  ω     60.00 110.00   0.50    4.00    --   76.98-125.00-150.00  100
 41  ω     42.00  72.00   0.50    4.00    --   76.98 -94.00-120.00   60
 42  ω     76.00 102.00   0.50    4.00    --   76.98  15.00-180.00   52
 43  ω     96.00 121.00   0.50    4.00    --   81.25  16.00  88.04   50
 44  ω     50.00  85.00   0.50    4.00    --   81.25  16.00  88.04   70
 45  ω     65.00  95.00   0.50    4.00    --   81.25  20.00 -74.40   60
 46  ω     99.00 125.00   0.50    4.00    --   81.25  14.00 128.47   52
 47  ω     42.00 120.00   0.50    4.00    --   81.25   5.00 -75.11  156
 48  ω     48.00  83.00   0.50    4.00    --   81.25  21.00 -95.57   70
 49  ω     35.00 106.00   0.50    4.00    --   81.25-111.00 -51.53  142
 50  ω     40.00  66.00   0.50    4.00    --   81.25 -71.00  43.09   52
 51  ω     48.00 126.00   0.50    4.00    --   81.25  21.00   9.11  156
 52  ω     35.00 106.00   0.50    4.00    --   81.25-114.00  65.59  142
 53  ω     48.00  81.00   0.50    4.00    --   81.25  21.00 -26.16   66
 54  ω    107.00 132.00   0.50    4.00    --   81.25  20.00 -74.40   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1035401000
_diffrn_orient_matrix_UB_12      0.0671292000
_diffrn_orient_matrix_UB_13      0.0278184000
_diffrn_orient_matrix_UB_21      -0.0360017000
_diffrn_orient_matrix_UB_22      0.0826348000
_diffrn_orient_matrix_UB_23      0.0589808000
_diffrn_orient_matrix_UB_31      0.0207865000
_diffrn_orient_matrix_UB_32      -0.1914461000
_diffrn_orient_matrix_UB_33      0.0353237000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3796
_reflns_number_total             4126
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+1.2040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.27521(2) 0.65551(3) 0.44439(2) 0.03184(7) Uani 1 1 d . . . . .
O2 O 0.74939(8) 0.08628(16) 0.82098(5) 0.0232(2) Uani 1 1 d . . . . .
O8 O 0.52375(10) -0.07980(18) 0.61105(6) 0.0390(3) Uani 1 1 d . . . . .
O9 O 0.57907(8) 0.16699(15) 0.67554(5) 0.0224(2) Uani 1 1 d . . . . .
O19 O 0.92372(8) 0.33004(16) 0.83441(6) 0.0278(3) Uani 1 1 d . . . . .
C1 C 0.35180(11) 0.4809(2) 0.50059(7) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.34003(12) 0.2881(3) 0.48925(8) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.293380 0.242285 0.454305 0.033 Uiso 1 1 calc R U . . .
C3 C 0.39769(12) 0.1635(2) 0.52994(8) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.391182 0.030507 0.522530 0.034 Uiso 1 1 calc R U . . .
C4 C 0.46537(11) 0.2307(2) 0.58177(7) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.47583(11) 0.4255(2) 0.59171(7) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.522169 0.472045 0.626706 0.027 Uiso 1 1 calc R U . . .
C6 C 0.41934(11) 0.5521(2) 0.55107(7) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.426680 0.685403 0.557640 0.029 Uiso 1 1 calc R U . . .
C7 C 0.52495(12) 0.0877(2) 0.62365(8) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.64289(11) 0.0468(2) 0.72228(7) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.58395(12) -0.1022(2) 0.75052(8) 0.0279(3) Uani 1 1 d . . . . .
H11A H 0.525566 -0.043011 0.761029 0.042 Uiso 1 1 calc R U . . .
H11B H 0.622947 -0.155423 0.789695 0.042 Uiso 1 1 calc R U . . .
H11C H 0.565381 -0.203980 0.719005 0.042 Uiso 1 1 calc R U . . .
C12 C 0.72212(12) -0.0416(3) 0.69170(8) 0.0289(4) Uani 1 1 d . . . . .
H12A H 0.694280 -0.141231 0.661489 0.043 Uiso 1 1 calc R U . . .
H12B H 0.771599 -0.097128 0.725312 0.043 Uiso 1 1 calc R U . . .
H12C H 0.751648 0.056531 0.668545 0.043 Uiso 1 1 calc R U . . .
C13 C 0.68327(11) 0.1922(2) 0.77492(8) 0.0227(3) Uani 1 1 d . . . . .
H13 H 0.629002 0.237864 0.795794 0.027 Uiso 1 1 calc R U . . .
C14 C 0.73421(13) 0.3634(2) 0.75275(8) 0.0288(4) Uani 1 1 d . . . . .
H14A H 0.688037 0.438572 0.721512 0.035 Uiso 1 1 calc R U . . .
H14B H 0.787594 0.320943 0.731279 0.035 Uiso 1 1 calc R U . . .
C15 C 0.77432(13) 0.4852(2) 0.81121(8) 0.0306(4) Uani 1 1 d . . . . .
H15A H 0.719862 0.537688 0.829609 0.037 Uiso 1 1 calc R U . . .
H15B H 0.810887 0.593307 0.797452 0.037 Uiso 1 1 calc R U . . .
C16 C 0.84082(12) 0.3716(2) 0.86301(8) 0.0253(3) Uani 1 1 d . . . . .
C17 C 0.79013(11) 0.1888(2) 0.87777(8) 0.0231(3) Uani 1 1 d . . . . .
H17 H 0.737823 0.220789 0.902432 0.028 Uiso 1 1 calc R U . . .
C18 C 0.86642(14) 0.4949(3) 0.92320(9) 0.0333(4) Uani 1 1 d . . . . .
H18A H 0.901877 0.418334 0.958567 0.050 Uiso 1 1 calc R U . . .
H18B H 0.806885 0.543780 0.935310 0.050 Uiso 1 1 calc R U . . .
H18C H 0.906946 0.601598 0.914358 0.050 Uiso 1 1 calc R U . . .
C20 C 0.99310(12) 0.1862(3) 0.86196(9) 0.0317(4) Uani 1 1 d . . . . .
C21 C 1.06392(13) 0.2642(3) 0.92003(11) 0.0430(5) Uani 1 1 d . . . . .
H21A H 1.088075 0.388574 0.909141 0.064 Uiso 1 1 calc R U . . .
H21B H 1.118403 0.176087 0.931360 0.064 Uiso 1 1 calc R U . . .
H21C H 1.030542 0.277934 0.956702 0.064 Uiso 1 1 calc R U . . .
C22 C 1.04739(16) 0.1429(3) 0.80761(12) 0.0469(5) Uani 1 1 d . . . . .
H22A H 1.001855 0.095469 0.770228 0.070 Uiso 1 1 calc R U . . .
H22B H 1.096905 0.046179 0.821807 0.070 Uiso 1 1 calc R U . . .
H22C H 1.078418 0.259171 0.795747 0.070 Uiso 1 1 calc R U . . .
C23 C 0.94253(12) 0.0074(2) 0.88000(8) 0.0289(4) Uani 1 1 d . . . . .
H23A H 0.990834 -0.075295 0.906839 0.035 Uiso 1 1 calc R U . . .
H23B H 0.915756 -0.063448 0.840246 0.035 Uiso 1 1 calc R U . . .
C24 C 0.86080(12) 0.0504(2) 0.91673(8) 0.0270(3) Uani 1 1 d . . . . .
H24A H 0.826781 -0.068787 0.923985 0.032 Uiso 1 1 calc R U . . .
H24B H 0.887772 0.106538 0.959185 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.8999(16) . ?
O2 C13 1.4266(18) . ?
O2 C17 1.4271(19) . ?
O8 C7 1.207(2) . ?
O9 C7 1.3369(19) . ?
O9 C10 1.4732(18) . ?
O19 C16 1.435(2) . ?
O19 C20 1.451(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.389(2) . ?
C4 C7 1.492(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C10 C11 1.522(2) . ?
C10 C12 1.517(2) . ?
C10 C13 1.540(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.517(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(2) . ?
C16 C17 1.528(2) . ?
C16 C18 1.527(2) . ?
C17 H17 1.0000 . ?
C17 C24 1.521(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.534(3) . ?
C20 C22 1.519(3) . ?
C20 C23 1.526(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.527(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C13 O2 C17 114.92(12) . . ?
C7 O9 C10 119.77(12) . . ?
C16 O19 C20 120.66(13) . . ?
C2 C1 Br1 119.29(12) . . ?
C2 C1 C6 122.12(15) . . ?
C6 C1 Br1 118.57(12) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.44(15) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.82(15) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 117.79(15) . . ?
C5 C4 C3 119.36(15) . . ?
C5 C4 C7 122.84(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.71(15) . . ?
C5 C6 H6 120.6 . . ?
O8 C7 O9 124.81(15) . . ?
O8 C7 C4 122.89(15) . . ?
O9 C7 C4 112.30(14) . . ?
O9 C10 C11 110.43(12) . . ?
O9 C10 C12 110.71(12) . . ?
O9 C10 C13 101.70(12) . . ?
C11 C10 C13 109.21(13) . . ?
C12 C10 C11 112.18(14) . . ?
C12 C10 C13 112.13(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C10 104.76(12) . . ?
O2 C13 H13 108.7 . . ?
O2 C13 C14 109.85(13) . . ?
C10 C13 H13 108.7 . . ?
C14 C13 C10 115.85(14) . . ?
C14 C13 H13 108.7 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
C13 C14 C15 108.76(14) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 111.98(14) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
O19 C16 C15 104.01(13) . . ?
O19 C16 C17 110.98(13) . . ?
O19 C16 C18 112.30(14) . . ?
C17 C16 C15 109.78(13) . . ?
C18 C16 C15 108.69(14) . . ?
C18 C16 C17 110.83(14) . . ?
O2 C17 C16 112.59(13) . . ?
O2 C17 H17 109.3 . . ?
O2 C17 C24 104.71(13) . . ?
C16 C17 H17 109.3 . . ?
C24 C17 C16 111.47(13) . . ?
C24 C17 H17 109.3 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O19 C20 C21 111.24(15) . . ?
O19 C20 C22 103.25(16) . . ?
O19 C20 C23 111.42(13) . . ?
C22 C20 C21 109.53(16) . . ?
C22 C20 C23 110.10(16) . . ?
C23 C20 C21 111.03(16) . . ?
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 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.0 . . ?
C20 C23 H23B 109.0 . . ?
C20 C23 C24 112.99(14) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C17 C24 C23 109.18(13) . . ?
C17 C24 H24A 109.8 . . ?
C17 C24 H24B 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?

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
Br1 C1 C2 C3 178.78(13) . . . . ?
Br1 C1 C6 C5 -179.40(11) . . . . ?
O2 C13 C14 C15 -58.34(17) . . . . ?
O2 C17 C24 C23 64.98(16) . . . . ?
O9 C10 C13 O2 -177.67(11) . . . . ?
O9 C10 C13 C14 -56.49(16) . . . . ?
O19 C16 C17 O2 -65.18(16) . . . . ?
O19 C16 C17 C24 52.15(17) . . . . ?
O19 C20 C23 C24 -46.6(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C7 179.92(15) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C7 O8 7.4(3) . . . . ?
C3 C4 C7 O9 -172.95(14) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C5 C4 C7 O8 -171.46(17) . . . . ?
C5 C4 C7 O9 8.2(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C7 O9 C10 C11 -59.90(18) . . . . ?
C7 O9 C10 C12 64.96(18) . . . . ?
C7 O9 C10 C13 -175.73(13) . . . . ?
C7 C4 C5 C6 179.40(15) . . . . ?
C10 O9 C7 O8 -0.2(2) . . . . ?
C10 O9 C7 C4 -179.81(12) . . . . ?
C10 C13 C14 C15 -176.75(14) . . . . ?
C11 C10 C13 O2 65.61(15) . . . . ?
C11 C10 C13 C14 -173.21(14) . . . . ?
C12 C10 C13 O2 -59.37(16) . . . . ?
C12 C10 C13 C14 61.82(18) . . . . ?
C13 O2 C17 C16 -55.85(17) . . . . ?
C13 O2 C17 C24 -177.12(12) . . . . ?
C13 C14 C15 C16 55.70(19) . . . . ?
C14 C15 C16 O19 68.01(17) . . . . ?
C14 C15 C16 C17 -50.80(19) . . . . ?
C14 C15 C16 C18 -172.18(15) . . . . ?
C15 C16 C17 O2 49.24(18) . . . . ?
C15 C16 C17 C24 166.57(14) . . . . ?
C16 O19 C20 C21 -80.21(19) . . . . ?
C16 O19 C20 C22 162.40(14) . . . . ?
C16 O19 C20 C23 44.3(2) . . . . ?
C16 C17 C24 C23 -57.02(17) . . . . ?
C17 O2 C13 C10 -174.76(12) . . . . ?
C17 O2 C13 C14 60.17(17) . . . . ?
C18 C16 C17 O2 169.32(13) . . . . ?
C18 C16 C17 C24 -73.35(17) . . . . ?
C20 O19 C16 C15 -165.10(13) . . . . ?
C20 O19 C16 C17 -47.11(18) . . . . ?
C20 O19 C16 C18 77.56(18) . . . . ?
C20 C23 C24 C17 54.64(18) . . . . ?
C21 C20 C23 C24 77.98(18) . . . . ?
C22 C20 C23 C24 -160.55(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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_cis_syn-(BA)-3
_database_code_depnum_ccdc_archive 'CCDC 2176604'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H38 O4'
_chemical_formula_sum            'C35 H38 O4'
_chemical_formula_weight         522.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35 H38 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.28197(17)
_cell_length_b                   12.2599(4)
_cell_length_c                   19.1503(5)
_cell_angle_alpha                89.562(2)
_cell_angle_beta                 87.114(2)
_cell_angle_gamma                78.209(3)
_cell_volume                     1441.93(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16059
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.2430
_cell_measurement_theta_min      2.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0131
0 0 -1 0.0089
0 -1 0 0.0059
0 1 0 0.0114
1 0 0 0.1860
-1 0 0 0.1597

_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.017
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
-0.0002 0.0021 1.0004 0.0136 0.0794 0.0014
0.0002 -0.0021 -1.0004 -0.0136 -0.0794 -0.0014
-0.0010 -0.9997 0.0062 -0.1235 0.0213 -0.0272
0.0010 0.9997 -0.0062 0.1235 -0.0213 0.0272
0.9986 -0.0088 0.0040 -0.1038 0.0009 0.2282
-0.9986 0.0088 -0.0040 0.1038 -0.0009 -0.2282

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35849
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.519
_diffrn_reflns_theta_min         2.310
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.959
_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 -25.00   0.50    7.00    --  -59.37 -15.00  60.00   62
  2  ω    -96.00 -53.00   0.50    7.00    --  -59.37   0.00-180.00   86
  3  ω   -106.00 -64.00   0.50    7.00    --  -59.37 -15.00  60.00   84
  4  ω    -71.00 -18.00   0.50    7.00    --  -59.37   0.00-150.00  106
  5  ω    -99.00 -35.00   0.50    7.00    --  -59.37   0.00 -60.00  128
  6  ω    -79.00 -53.00   0.50    7.00    --  -59.37 125.00 120.00   52
  7  ω     18.00  66.00   0.50    7.00    --   59.80 -94.00-120.00   96
  8  ω     18.00  54.00   0.50    7.00    --   59.80 -94.00   0.00   72
  9  ω     19.00  71.00   0.50    7.00    --   59.80 -94.00 120.00  104
 10  ω     19.00  72.00   0.50    7.00    --   59.80 -94.00 -60.00  106
 11  ω     19.00  50.00   0.50    7.00    --   59.80 -94.00  60.00   62
 12  ω     59.00  85.00   0.50    7.00    --   73.77 -94.00  30.00   52
 13  ω     40.00  66.00   0.50    7.00    --   76.98 -94.00-120.00   52
 14  ω     43.00  84.00   0.50    7.00    --   76.98  15.00  30.00   82
 15  ω     36.00  85.00   0.50    7.00    --   76.98 -94.00 -30.00   98
 16  ω     53.00  79.00   0.50    7.00    --   76.98 -94.00-150.00   52
 17  ω     60.00  86.00   0.50    7.00    --   76.98 -94.00 120.00   52
 18  ω     35.00  60.00   0.50    7.00    --   76.98 -94.00  60.00   50
 19  ω     43.00  84.00   0.50    7.00    --   76.98 -94.00  30.00   82
 20  ω     75.00 100.00   0.50    7.00    --   76.98-125.00   0.00   50
 21  ω     36.00  65.00   0.50    7.00    --   76.98-125.00-150.00   58
 22  ω     77.00 114.00   0.50    7.00    --   76.98  15.00 -90.00   74
 23  ω     92.00 117.00   0.50    7.00    --   76.98  15.00  60.00   50
 24  ω     58.00  84.00   0.50    7.00    --   76.98-125.00  60.00   52
 25  ω     48.00  97.00   0.50    7.00    --   76.98-125.00 150.00   98
 26  ω     37.00  86.00   0.50    7.00    --   76.98 -94.00 150.00   98
 27  ω     42.00  85.00   0.50    7.00    --   76.98 -94.00 -90.00   86
 28  ω     43.00  79.00   0.50    7.00    --   76.98 -94.00 -60.00   72
 29  ω     35.00  85.00   0.50    7.00    --   78.00 -98.00-127.08  100
 30  ω     41.00  79.00   0.50    7.00    --   81.25 -93.00  72.05   76
 31  ω     78.00 106.00   0.50    7.00    --   81.25-114.00  30.45   56
 32  ω     34.00  73.00   0.50    7.00    --   81.25-114.00  30.45   78
 33  ω     63.00 122.00   0.50    7.00    --   81.25  20.00 -51.30  118
 34  ω     78.00 129.00   0.50    7.00    --   81.25  16.00 153.29  102
 35  ω     40.00 117.00   0.50    7.00    --   81.25-132.00 124.89  154
 36  ω     86.00 114.00   0.50    7.00    --   81.25-129.00  30.29   56
 37  ω     83.00 108.00   0.50    7.00    --   81.25-126.00-129.81   50
 38  ω     43.00  76.00   0.50    7.00    --   81.25-126.00-129.81   66
 39  ω     45.00 101.00   0.50    7.00    --   81.25  12.00 128.54  112
 40  ω     60.00 129.00   0.50    7.00    --   81.25  10.00-133.94  138
 41  ω     42.00  67.00   0.50    7.00    --   81.25 -74.00 108.03   50
 42  ω     38.00  80.00   0.50    7.00    --   81.25-129.00  30.29   84
 43  ω     73.00 124.00   0.50    7.00    --   81.25-141.00 -41.41  102
 44  ω      1.00  30.00   0.50    7.00    --   -2.00  33.00-112.12   58
 45  ω     10.00  37.00   0.50    7.00    --    6.00  30.00  43.73   54
 46  ω      5.00  31.00   0.50    7.00    --    6.00  31.00 -58.25   52
 47  ω     11.00  37.00   0.50    7.00    --   10.00  30.00-145.19   52
 48  ω     10.00  37.00   0.50    7.00    --   14.00  28.00 -37.36   54
 49  ω     10.00  35.00   0.50    7.00    --   14.00  29.00 109.13   50
 50  ω     -6.00  21.00   0.50    7.00    --  -14.00  39.00  93.37   54
 51  ω     -3.00  23.00   0.50    7.00    --  -14.00  38.00 144.79   52
 52  ω    -11.00  15.00   0.50    7.00    --  -18.00  45.00  51.62   52
 53  ω     11.00  41.00   0.50    7.00    --   18.00  28.00  82.68   60
 54  ω    -51.00 -26.00   0.50    7.00    --  -42.00 -25.00-121.54   50
 55  ω    -50.00 -24.00   0.50    7.00    --  -42.00 -25.00 -40.75   52
 56  ω    -51.00 -26.00   0.50    7.00    --  -42.00 -25.00 171.42   50
 57  ω    -50.00 -24.00   0.50    7.00    --  -42.00 -25.00  35.85   52
 58  ω    -56.00 -31.00   0.50    7.00    --  -50.00 -24.00  21.83   50
 59  ω    -56.00 -31.00   0.50    7.00    --  -50.00 -24.00 -50.62   50
 60  ω    -61.00 -35.00   0.50    7.00    --  -58.00 -23.00-142.67   52
 61  ω    -62.00 -35.00   0.50    7.00    --  -58.00 -23.00 147.62   54
 62  ω    -61.00 -35.00   0.50    7.00    --  -58.00 -23.00 110.38   52
 63  ω    -62.00 -36.00   0.50    7.00    --  -58.00 -23.00  81.84   52
 64  ω    -56.00 -27.00   0.50    7.00    --  -59.37 137.00 112.00   58
 65  ω   -101.00 -76.00   0.50    7.00    --  -59.37   0.00 150.00   50
 66  ω    -99.00 -66.00   0.50    7.00    --  -59.37   0.00  30.00   66
 67  ω    -54.00 -28.00   0.50    7.00    --  -59.37 132.00 -64.00   52
 68  ω    -45.00 -18.00   0.50    7.00    --  -59.37   0.00  30.00   54
 69  ω    -71.00 -40.00   0.50    7.00    --  -66.50 -22.00-153.61   62
 70  ω    -71.00 -46.00   0.50    7.00    --  -66.50 -22.00-173.61   50
 71  ω     77.00 104.00   0.50    7.00    --   66.78  21.00 119.28   54
 72  ω     35.00  61.00   0.50    7.00    --   66.78  21.00 119.28   52
 73  ω     35.00  62.00   0.50    7.00    --   76.98-125.00 -60.00   54
 74  ω     35.00 111.00   0.50    7.00    --   76.98   0.00 120.00  152
 75  ω     36.00 116.00   0.50    7.00    --   76.98   0.00  30.00  160
 76  ω     40.00  66.00   0.50    7.00    --   76.98-125.00-180.00   52
 77  ω     90.00 116.00   0.50    7.00    --   76.98   0.00-180.00   52
 78  ω     55.00  88.00   0.50    7.00    --   76.98   0.00-180.00   66
 79  ω     35.00  61.00   0.50    7.00    --   76.98-125.00 -30.00   52
 80  ω     84.00 119.00   0.50    7.00    --   76.98   0.00 -60.00   70
 81  ω     45.00  76.00   0.50    7.00    --   76.98   0.00 -60.00   62
 82  ω     38.00  78.00   0.50    7.00    --   81.25-130.00  81.29   80
 83  ω    107.00 132.00   0.50    7.00    --   81.25  19.00-133.32   50
 84  ω     48.00 116.00   0.50    7.00    --   81.25  21.00  53.55  136
 85  ω     44.00  88.00   0.50    7.00    --   81.25  19.00-133.32   88
 86  ω     94.00 119.00   0.50    7.00    --   81.25  19.00  30.07   50
 87  ω     46.00  74.00   0.50    7.00    --   81.25  19.00  30.07   56
 88  ω    107.00 132.00   0.50    7.00    --   81.25  21.00 -66.49   50
 89  ω     51.00  86.00   0.50    7.00    --   81.25  21.00 126.22   70
 90  ω     37.00  63.00   0.50    7.00    --   81.25-114.00 124.86   52
 91  ω     50.00  77.00   0.50    7.00    --   81.25  21.00 -66.49   54
 92  ω     34.00  68.00   0.50    7.00    --   81.25-113.00 -13.75   68
 93  ω     44.00  74.00   0.50    7.00    --   81.25  20.00 -88.86   60
 94  ω     52.00  96.00   0.50    7.00    --   81.25  21.00 165.31   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1028869000
_diffrn_orient_matrix_UB_12      0.1237702000
_diffrn_orient_matrix_UB_13      0.0132641000
_diffrn_orient_matrix_UB_21      0.0004104000
_diffrn_orient_matrix_UB_22      -0.0207958000
_diffrn_orient_matrix_UB_23      0.0794361000
_diffrn_orient_matrix_UB_31      0.2287610000
_diffrn_orient_matrix_UB_32      0.0269579000
_diffrn_orient_matrix_UB_33      0.0014204000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4972
_reflns_number_total             5658
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5658
_refine_ls_number_restraints     113
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.085
_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)+(0.0808P)²+1.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O35-C34B \\sim O35B-C34
 with sigma of 0.02
 C37B-C36B \\sim C37-C36
 with sigma of 0.02
 O35-C36B \\sim O35B-C36
 with sigma of 0.02
 C40B-C34B \\sim C40-C34
 with sigma of 0.02
 C39B-C36B \\sim C39-C36 \\sim C38B-C36B \\sim C38-C36
 with sigma of 0.02
 C40B-C37B \\sim C40-C37
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O35B) = Uanis(O35)
4. Rigid body (RIGU) restrains
 O35, C34B, C36B, C37B, C38B, C39B, C40B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O35B, C34, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O35)=Sof(C34B)=Sof(H34B)=Sof(C36B)=Sof(C37B)=Sof(H37C)=Sof(H37D)=
 Sof(C38B)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39B)=Sof(H39D)=Sof(H39E)=
 Sof(H39F)=Sof(C40B)=Sof(H40C)=Sof(H40D)=1-FVAR(1)
 Sof(O35B)=Sof(C34)=Sof(H34)=Sof(C36)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=
 Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40)=
 Sof(H40A)=Sof(H40B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C24(H24), C34(H34), C34B(H34B)
6.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C37(H37A,H37B), C37B(H37C,H37D), C40(H40A,
 H40B), C40B(H40C,H40D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C16(H16), C17(H17), C19(H19), C20(H20)
6.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C38(H38A,H38B,
 H38C), C38B(H38D,H38E,H38F), C39(H39A,H39B,H39C), C39B(H39D,H39E,H39F)
;
_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
O22 O 0.4058(3) 0.84543(14) 0.29305(9) 0.0354(4) Uani 1 1 d . . . . .
O23 O 0.7443(3) 0.78688(14) 0.24549(9) 0.0332(4) Uani 1 1 d . . . . .
O32 O 0.8634(3) 0.96461(14) 0.10121(8) 0.0354(4) Uani 1 1 d . . . . .
O35 O 0.883(3) 1.2577(14) 0.1162(14) 0.053(2) Uani 0.433(7) 1 d D . P A 1
O35B O 0.926(2) 1.2468(10) 0.1068(10) 0.053(2) Uani 0.567(7) 1 d D . P A 2
C1 C 0.9627(4) 0.35417(19) 0.47818(12) 0.0298(5) Uani 1 1 d . . . . .
H1 H 0.962603 0.426475 0.459981 0.036 Uiso 1 1 calc R U . . .
C2 C 1.1085(4) 0.3114(2) 0.52622(13) 0.0340(5) Uani 1 1 d . . . . .
H2 H 1.212457 0.352546 0.539725 0.041 Uiso 1 1 calc R U . . .
C3 C 1.1065(4) 0.2053(2) 0.55644(13) 0.0356(6) Uani 1 1 d . . . . .
H3 H 1.207012 0.176805 0.590822 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9627(4) 0.1450(2) 0.53657(12) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.961952 0.074715 0.557740 0.040 Uiso 1 1 calc R U . . .
C5 C 0.8116(4) 0.18477(19) 0.48432(12) 0.0295(5) Uani 1 1 d . . . . .
C6 C 0.6693(4) 0.12118(19) 0.46092(12) 0.0309(5) Uani 1 1 d . . . . .
H6 H 0.668876 0.050520 0.481572 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5285(4) 0.15794(19) 0.40842(12) 0.0291(5) Uani 1 1 d . . . . .
C8 C 0.3897(4) 0.0902(2) 0.38247(13) 0.0338(5) Uani 1 1 d . . . . .
H8 H 0.391315 0.019001 0.402599 0.041 Uiso 1 1 calc R U . . .
C9 C 0.2561(4) 0.1250(2) 0.32996(14) 0.0371(6) Uani 1 1 d . . . . .
H9 H 0.164666 0.078606 0.313814 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2526(4) 0.2307(2) 0.29908(14) 0.0365(6) Uani 1 1 d . . . . .
H10 H 0.160603 0.254236 0.261628 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3798(4) 0.2987(2) 0.32255(12) 0.0314(5) Uani 1 1 d . . . . .
H11 H 0.374223 0.369477 0.301312 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5215(4) 0.26620(19) 0.37838(12) 0.0277(5) Uani 1 1 d . . . . .
C13 C 0.6592(4) 0.33362(19) 0.40309(12) 0.0275(5) Uani 1 1 d . . . . .
C14 C 0.8090(4) 0.29306(18) 0.45425(12) 0.0273(5) Uani 1 1 d . . . . .
C15 C 0.6434(4) 0.44810(19) 0.37442(11) 0.0266(5) Uani 1 1 d . . . . .
C16 C 0.4524(4) 0.52876(19) 0.38673(12) 0.0298(5) Uani 1 1 d . . . . .
H16 H 0.336340 0.510841 0.415293 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4303(4) 0.63375(19) 0.35805(12) 0.0283(5) Uani 1 1 d . . . . .
H17 H 0.299196 0.687248 0.366603 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6000(4) 0.66150(18) 0.31651(11) 0.0263(5) Uani 1 1 d . . . . .
C19 C 0.7935(4) 0.5825(2) 0.30570(12) 0.0308(5) Uani 1 1 d . . . . .
H19 H 0.911539 0.601105 0.278462 0.037 Uiso 1 1 calc R U . . .
C20 C 0.8136(4) 0.4781(2) 0.33427(12) 0.0311(5) Uani 1 1 d . . . . .
H20 H 0.946029 0.425256 0.326544 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5681(4) 0.77428(19) 0.28499(11) 0.0263(5) Uani 1 1 d . . . . .
C24 C 0.7329(4) 0.89140(19) 0.20806(12) 0.0290(5) Uani 1 1 d . . . . .
H24 H 0.577103 0.924084 0.199582 0.035 Uiso 1 1 calc R U . . .
C25 C 0.8239(4) 0.9729(2) 0.25036(12) 0.0328(5) Uani 1 1 d . . . . .
H25A H 0.978705 0.942577 0.259175 0.039 Uiso 1 1 calc R U . . .
H25B H 0.741488 0.987763 0.295891 0.039 Uiso 1 1 calc R U . . .
C26 C 0.8020(4) 1.0805(2) 0.20733(14) 0.0360(6) Uani 1 1 d . . . . .
H26A H 0.863545 1.135902 0.232779 0.043 Uiso 1 1 calc R U . . .
H26B H 0.646025 1.112131 0.201132 0.043 Uiso 1 1 calc R U . . .
C27 C 0.9218(4) 1.0573(2) 0.13534(13) 0.0367(6) Uani 1 1 d . . . . .
C29 C 0.8565(4) 0.8623(2) 0.13779(12) 0.0314(5) Uani 1 1 d . . . . .
C30 C 0.7260(5) 0.8031(2) 0.09126(14) 0.0428(6) Uani 1 1 d . . . . .
H30A H 0.583311 0.851101 0.084613 0.064 Uiso 1 1 calc R U . . .
H30B H 0.706152 0.733308 0.113442 0.064 Uiso 1 1 calc R U . . .
H30C H 0.804386 0.786769 0.045782 0.064 Uiso 1 1 calc R U . . .
C31 C 1.0835(4) 0.7901(2) 0.14542(14) 0.0395(6) Uani 1 1 d . . . . .
H31A H 1.172166 0.793155 0.102129 0.059 Uiso 1 1 calc R U . . .
H31B H 1.071033 0.712855 0.154664 0.059 Uiso 1 1 calc R U . . .
H31C H 1.152822 0.818012 0.184371 0.059 Uiso 1 1 calc R U . . .
C33 C 1.1677(4) 1.0396(3) 0.14170(16) 0.0470(7) Uani 1 1 d . . . B 5
H33A H 1.212878 0.984472 0.178201 0.070 Uiso 1 1 calc R U . B 5
H33B H 1.206401 1.110288 0.154001 0.070 Uiso 1 1 calc R U . B 5
H33C H 1.241792 1.012671 0.096975 0.070 Uiso 1 1 calc R U . B 5
C34 C 0.8545(14) 1.1520(9) 0.0809(5) 0.0292(17) Uani 0.567(7) 1 d D . P A 2
H34 H 0.939319 1.128624 0.036064 0.035 Uiso 0.567(7) 1 calc R U P A 2
C34B C 0.860(3) 1.1518(17) 0.0885(11) 0.070(5) Uani 0.433(7) 1 d D . P A 1
H34B H 0.955616 1.136854 0.044915 0.084 Uiso 0.433(7) 1 calc R U P A 1
C36 C 0.7529(17) 1.3448(8) 0.1004(4) 0.044(2) Uani 0.567(7) 1 d D . P A 2
C36B C 0.713(2) 1.3481(13) 0.0924(7) 0.055(3) Uani 0.433(7) 1 d D . P A 1
C37 C 0.5517(9) 1.2955(4) 0.1021(3) 0.0468(14) Uani 0.567(7) 1 d D . P A 2
H37A H 0.501612 1.284185 0.150969 0.056 Uiso 0.567(7) 1 calc R U P A 2
H37B H 0.432811 1.345529 0.078548 0.056 Uiso 0.567(7) 1 calc R U P A 2
C37B C 0.5733(14) 1.3005(7) 0.0436(4) 0.059(2) Uani 0.433(7) 1 d D . P A 1
H37C H 0.618243 1.309174 -0.006127 0.071 Uiso 0.433(7) 1 calc R U P A 1
H37D H 0.416748 1.334153 0.051491 0.071 Uiso 0.433(7) 1 calc R U P A 1
C38 C 0.7946(14) 1.4001(6) 0.0319(3) 0.0527(17) Uani 0.567(7) 1 d D . P A 2
H38A H 0.943812 1.412874 0.029215 0.079 Uiso 0.567(7) 1 calc R U P A 2
H38B H 0.691708 1.471525 0.028779 0.079 Uiso 0.567(7) 1 calc R U P A 2
H38C H 0.775512 1.351799 -0.006871 0.079 Uiso 0.567(7) 1 calc R U P A 2
C38B C 0.829(2) 1.4329(11) 0.0570(7) 0.083(4) Uani 0.433(7) 1 d D . P A 1
H38D H 0.932473 1.395826 0.020386 0.125 Uiso 0.433(7) 1 calc R U P A 1
H38E H 0.906802 1.465619 0.091672 0.125 Uiso 0.433(7) 1 calc R U P A 1
H38F H 0.721309 1.491766 0.036079 0.125 Uiso 0.433(7) 1 calc R U P A 1
C39 C 0.7622(14) 1.4191(6) 0.1627(3) 0.070(2) Uani 0.567(7) 1 d D . P A 2
H39A H 0.753456 1.376667 0.205980 0.104 Uiso 0.567(7) 1 calc R U P A 2
H39B H 0.639766 1.483039 0.162673 0.104 Uiso 0.567(7) 1 calc R U P A 2
H39C H 0.899477 1.445489 0.159725 0.104 Uiso 0.567(7) 1 calc R U P A 2
C39B C 0.569(2) 1.4013(10) 0.1549(5) 0.092(3) Uani 0.433(7) 1 d D . P A 1
H39D H 0.658457 1.429609 0.188107 0.138 Uiso 0.433(7) 1 calc R U P A 1
H39E H 0.498481 1.345371 0.177975 0.138 Uiso 0.433(7) 1 calc R U P A 1
H39F H 0.457404 1.462942 0.138696 0.138 Uiso 0.433(7) 1 calc R U P A 1
C40 C 0.6147(16) 1.1863(8) 0.0644(7) 0.041(3) Uani 0.567(7) 1 d D . P A 2
H40A H 0.596415 1.195289 0.013521 0.050 Uiso 0.567(7) 1 calc R U P A 2
H40B H 0.529622 1.131848 0.082959 0.050 Uiso 0.567(7) 1 calc R U P A 2
C40B C 0.626(3) 1.1790(11) 0.0669(11) 0.063(5) Uani 0.433(7) 1 d D . P A 1
H40C H 0.526827 1.167303 0.106741 0.075 Uiso 0.433(7) 1 calc R U P A 1
H40D H 0.607162 1.129605 0.028057 0.075 Uiso 0.433(7) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O22 C21 1.203(3) . ?
O23 C21 1.343(3) . ?
O23 C24 1.454(3) . ?
O32 C27 1.435(3) . ?
O32 C29 1.440(3) . ?
O35 C34B 1.444(13) . ?
O35 C36B 1.459(13) . ?
O35B C34 1.429(9) . ?
O35B C36 1.455(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.357(3) . ?
C1 C14 1.431(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.421(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.349(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.428(3) . ?
C5 C6 1.392(3) . ?
C5 C14 1.440(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 C8 1.429(3) . ?
C7 C12 1.436(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.353(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.417(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.361(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.428(3) . ?
C12 C13 1.412(3) . ?
C13 C14 1.409(3) . ?
C13 C15 1.489(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.394(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.394(3) . ?
C18 C19 1.399(3) . ?
C18 C21 1.484(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(3) . ?
C20 H20 0.9500 . ?
C24 H24 1.0000 . ?
C24 C25 1.508(3) . ?
C24 C29 1.526(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.535(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.537(4) . ?
C27 C33 1.526(4) . ?
C27 C34 1.561(10) . ?
C27 C34B 1.46(2) . ?
C29 C30 1.523(3) . ?
C29 C31 1.530(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 1.0000 . ?
C34 C40 1.527(8) . ?
C34B H34B 1.0000 . ?
C34B C40B 1.513(13) . ?
C36 C37 1.507(10) . ?
C36 C38 1.508(9) . ?
C36 C39 1.517(9) . ?
C36B C37B 1.512(13) . ?
C36B C38B 1.522(12) . ?
C36B C39B 1.529(13) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C40 1.496(10) . ?
C37B H37C 0.9900 . ?
C37B H37D 0.9900 . ?
C37B C40B 1.527(13) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C38B H38D 0.9800 . ?
C38B H38E 0.9800 . ?
C38B H38F 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C39B H39D 0.9800 . ?
C39B H39E 0.9800 . ?
C39B H39F 0.9800 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40B H40C 0.9900 . ?
C40B H40D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O23 C24 117.53(17) . . ?
C27 O32 C29 121.42(18) . . ?
C34B O35 C36B 111.2(17) . . ?
C34 O35B C36 108.8(11) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C14 121.6(2) . . ?
C14 C1 H1 119.2 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C14 119.0(2) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 C14 119.1(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 C12 119.8(2) . . ?
C8 C7 C12 118.6(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 117.7(2) . . ?
C13 C12 C7 119.2(2) . . ?
C13 C12 C11 123.0(2) . . ?
C12 C13 C15 119.0(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 C15 120.6(2) . . ?
C1 C14 C5 117.3(2) . . ?
C13 C14 C1 123.2(2) . . ?
C13 C14 C5 119.5(2) . . ?
C16 C15 C13 120.0(2) . . ?
C20 C15 C13 121.9(2) . . ?
C20 C15 C16 118.1(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 C21 118.6(2) . . ?
C19 C18 C21 122.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
O22 C21 O23 124.0(2) . . ?
O22 C21 C18 124.8(2) . . ?
O23 C21 C18 111.18(19) . . ?
O23 C24 H24 108.8 . . ?
O23 C24 C25 110.65(18) . . ?
O23 C24 C29 106.37(18) . . ?
C25 C24 H24 108.8 . . ?
C25 C24 C29 113.17(19) . . ?
C29 C24 H24 108.8 . . ?
C24 C25 H25A 110.4 . . ?
C24 C25 H25B 110.4 . . ?
C24 C25 C26 106.83(19) . . ?
H25A C25 H25B 108.6 . . ?
C26 C25 H25A 110.4 . . ?
C26 C25 H25B 110.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 C27 110.7(2) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
O32 C27 C26 111.47(19) . . ?
O32 C27 C33 111.3(2) . . ?
O32 C27 C34 101.2(4) . . ?
O32 C27 C34B 105.2(8) . . ?
C26 C27 C34 113.9(4) . . ?
C33 C27 C26 110.8(2) . . ?
C34B C27 C26 110.8(9) . . ?
O32 C29 C24 108.10(19) . . ?
O32 C29 C30 103.61(19) . . ?
O32 C29 C31 112.3(2) . . ?
C24 C29 C31 112.65(19) . . ?
C30 C29 C24 110.0(2) . . ?
C30 C29 C31 109.7(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C27 C33 H33A 109.5 . . ?
C27 C33 H33B 109.5 . . ?
C27 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O35B C34 C27 105.9(10) . . ?
O35B C34 H34 107.6 . . ?
O35B C34 C40 109.0(10) . . ?
C27 C34 H34 107.6 . . ?
C40 C34 C27 118.6(7) . . ?
C40 C34 H34 107.6 . . ?
O35 C34B C27 114.7(17) . . ?
O35 C34B H34B 107.6 . . ?
O35 C34B C40B 101.2(17) . . ?
C27 C34B H34B 107.6 . . ?
C27 C34B C40B 117.7(14) . . ?
C40B C34B H34B 107.6 . . ?
O35B C36 C37 102.5(8) . . ?
O35B C36 C38 107.5(11) . . ?
O35B C36 C39 106.9(8) . . ?
C37 C36 C38 113.4(7) . . ?
C37 C36 C39 113.4(7) . . ?
C38 C36 C39 112.3(7) . . ?
O35 C36B C37B 108.7(13) . . ?
O35 C36B C38B 106.6(14) . . ?
O35 C36B C39B 109.9(13) . . ?
C37B C36B C38B 112.8(11) . . ?
C37B C36B C39B 108.5(10) . . ?
C38B C36B C39B 110.3(11) . . ?
C36 C37 H37A 110.5 . . ?
C36 C37 H37B 110.5 . . ?
H37A C37 H37B 108.7 . . ?
C40 C37 C36 106.3(7) . . ?
C40 C37 H37A 110.5 . . ?
C40 C37 H37B 110.5 . . ?
C36B C37B H37C 112.0 . . ?
C36B C37B H37D 112.0 . . ?
C36B C37B C40B 99.0(10) . . ?
H37C C37B H37D 109.7 . . ?
C40B C37B H37C 112.0 . . ?
C40B C37B H37D 112.0 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36B C38B H38D 109.5 . . ?
C36B C38B H38E 109.5 . . ?
C36B C38B H38F 109.5 . . ?
H38D C38B H38E 109.5 . . ?
H38D C38B H38F 109.5 . . ?
H38E C38B H38F 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36B C39B H39D 109.5 . . ?
C36B C39B H39E 109.5 . . ?
C36B C39B H39F 109.5 . . ?
H39D C39B H39E 109.5 . . ?
H39D C39B H39F 109.5 . . ?
H39E C39B H39F 109.5 . . ?
C34 C40 H40A 111.6 . . ?
C34 C40 H40B 111.6 . . ?
C37 C40 C34 101.0(8) . . ?
C37 C40 H40A 111.6 . . ?
C37 C40 H40B 111.6 . . ?
H40A C40 H40B 109.4 . . ?
C34B C40B C37B 108.6(14) . . ?
C34B C40B H40C 110.0 . . ?
C34B C40B H40D 110.0 . . ?
C37B C40B H40C 110.0 . . ?
C37B C40B H40D 110.0 . . ?
H40C C40B H40D 108.4 . . ?

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
O23 C24 C25 C26 -179.19(18) . . . . ?
O23 C24 C29 O32 -175.66(17) . . . . ?
O23 C24 C29 C30 71.8(2) . . . . ?
O23 C24 C29 C31 -50.9(3) . . . . ?
O32 C27 C34 O35B -174.4(7) . . . . ?
O32 C27 C34 C40 62.9(9) . . . . ?
O32 C27 C34B O35 173.7(14) . . . . ?
O32 C27 C34B C40B 54.9(18) . . . . ?
O35 C34B C40B C37B 32(2) . . . . ?
O35 C36B C37B C40B 21.3(16) . . . . ?
O35B C34 C40 C37 -15.3(13) . . . . ?
O35B C36 C37 C40 -35.7(11) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C1 C14 C5 1.3(3) . . . . ?
C2 C1 C14 C13 -178.3(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 176.9(2) . . . . ?
C3 C4 C5 C14 -2.1(3) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C4 C5 C14 C1 1.0(3) . . . . ?
C4 C5 C14 C13 -179.4(2) . . . . ?
C5 C6 C7 C8 177.2(2) . . . . ?
C5 C6 C7 C12 -2.2(3) . . . . ?
C6 C5 C14 C1 -178.0(2) . . . . ?
C6 C5 C14 C13 1.6(3) . . . . ?
C6 C7 C8 C9 -178.3(2) . . . . ?
C6 C7 C12 C11 177.6(2) . . . . ?
C6 C7 C12 C13 0.0(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C7 C12 C13 C14 3.0(3) . . . . ?
C7 C12 C13 C15 -176.88(19) . . . . ?
C8 C7 C12 C11 -1.8(3) . . . . ?
C8 C7 C12 C13 -179.4(2) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C10 C11 C12 C13 178.6(2) . . . . ?
C11 C12 C13 C14 -174.5(2) . . . . ?
C11 C12 C13 C15 5.6(3) . . . . ?
C12 C7 C8 C9 1.1(3) . . . . ?
C12 C13 C14 C1 175.8(2) . . . . ?
C12 C13 C14 C5 -3.8(3) . . . . ?
C12 C13 C15 C16 65.1(3) . . . . ?
C12 C13 C15 C20 -114.0(3) . . . . ?
C13 C15 C16 C17 -177.0(2) . . . . ?
C13 C15 C20 C19 177.2(2) . . . . ?
C14 C1 C2 C3 -2.6(4) . . . . ?
C14 C5 C6 C7 1.5(3) . . . . ?
C14 C13 C15 C16 -114.8(3) . . . . ?
C14 C13 C15 C20 66.1(3) . . . . ?
C15 C13 C14 C1 -4.3(3) . . . . ?
C15 C13 C14 C5 176.1(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C15 C20 C19 -1.9(4) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C16 C17 C18 C21 178.4(2) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C17 C18 C21 O22 0.8(3) . . . . ?
C17 C18 C21 O23 -178.7(2) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C19 C18 C21 O22 -179.4(2) . . . . ?
C19 C18 C21 O23 1.0(3) . . . . ?
C20 C15 C16 C17 2.1(4) . . . . ?
C21 O23 C24 C25 93.6(2) . . . . ?
C21 O23 C24 C29 -143.1(2) . . . . ?
C21 C18 C19 C20 -178.2(2) . . . . ?
C24 O23 C21 O22 -2.7(3) . . . . ?
C24 O23 C21 C18 176.80(18) . . . . ?
C24 C25 C26 C27 -57.7(3) . . . . ?
C25 C24 C29 O32 -54.0(2) . . . . ?
C25 C24 C29 C30 -166.5(2) . . . . ?
C25 C24 C29 C31 70.8(3) . . . . ?
C25 C26 C27 O32 49.6(3) . . . . ?
C25 C26 C27 C33 -74.9(3) . . . . ?
C25 C26 C27 C34 163.4(4) . . . . ?
C25 C26 C27 C34B 166.5(8) . . . . ?
C26 C27 C34 O35B 65.9(8) . . . . ?
C26 C27 C34 C40 -56.8(9) . . . . ?
C26 C27 C34B O35 53.1(17) . . . . ?
C26 C27 C34B C40B -65.7(17) . . . . ?
C27 O32 C29 C24 46.9(3) . . . . ?
C27 O32 C29 C30 163.6(2) . . . . ?
C27 O32 C29 C31 -78.0(3) . . . . ?
C27 C34 C40 C37 105.8(9) . . . . ?
C27 C34B C40B C37B 158.2(14) . . . . ?
C29 O32 C27 C26 -46.3(3) . . . . ?
C29 O32 C27 C33 77.9(3) . . . . ?
C29 O32 C27 C34 -167.7(4) . . . . ?
C29 O32 C27 C34B -166.5(9) . . . . ?
C29 C24 C25 C26 61.5(2) . . . . ?
C34 O35B C36 C37 25.6(14) . . . . ?
C34 O35B C36 C38 -94.1(13) . . . . ?
C34 O35B C36 C39 145.2(11) . . . . ?
C34B O35 C36B C37B -2(2) . . . . ?
C34B O35 C36B C38B -124.2(18) . . . . ?
C34B O35 C36B C39B 116.2(19) . . . . ?
C36 O35B C34 C27 -135.2(11) . . . . ?
C36 O35B C34 C40 -6.6(16) . . . . ?
C36 C37 C40 C34 31.0(9) . . . . ?
C36B O35 C34B C27 -145.7(17) . . . . ?
C36B O35 C34B C40B -18(2) . . . . ?
C36B C37B C40B C34B -33.2(17) . . . . ?
C38 C36 C37 C40 79.9(9) . . . . ?
C38B C36B C37B C40B 139.2(14) . . . . ?
C39 C36 C37 C40 -150.6(8) . . . . ?
C39B C36B C37B C40B -98.3(13) . . . . ?

_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_trans_anti-(BA)-3
_database_code_depnum_ccdc_archive 'CCDC 2176605'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H29 Br O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   7.44418(10)
_cell_length_b                   11.53654(18)
_cell_length_c                   12.84945(19)
_cell_angle_alpha                69.1422(14)
_cell_angle_beta                 81.6780(12)
_cell_angle_gamma                84.3027(12)
_cell_volume                     1018.98(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18859
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.9720
_cell_measurement_theta_min      3.7060
_shelx_estimated_absorpt_T_max   0.778
_shelx_estimated_absorpt_T_min   0.445
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0431
0 0 1 0.0431
-5 0 0 0.1469
5 0 0 0.1469
0 -2 -1 0.1224
0 2 1 0.1224

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
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
-0.0000 -0.0008 -0.9997 -0.1287 0.0105 -0.0017
0.0000 0.0008 0.9997 0.1287 -0.0105 0.0017
-4.9979 -0.0001 -0.0002 0.0840 -0.3210 0.9927
4.9979 0.0001 0.0002 -0.0840 0.3210 -0.9927
0.0003 -1.9986 -0.9985 -0.0486 -0.2433 -0.1062
-0.0003 1.9986 0.9985 0.0486 0.2433 0.1062

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22323
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.780
_diffrn_reflns_theta_min         3.707
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  32.00   0.50    0.20    --    4.00  31.00  80.00   50
  2  ω      9.00  34.00   0.50    0.20    --    8.00  30.00 -61.19   50
  3  ω     11.00  38.00   0.50    0.20    --   12.00  29.00 -87.63   54
  4  ω      4.00  32.00   0.50    0.20    --    0.00  32.00-154.89   56
  5  ω    -56.00 -26.00   0.50    0.20    --  -64.50  73.00   3.64   60
  6  ω    -91.00 -38.00   0.50    0.20    --  -57.30   0.00 -90.00  106
  7  ω    -76.00 -36.00   0.50    0.20    --  -57.30   0.00 -30.00   80
  8  ω    -83.00 -18.00   0.50    0.20    --  -57.30   0.00  30.00  130
  9  ω    -95.00 -60.00   0.50    0.20    --  -57.30   0.00 120.00   70
 10  ω    -57.00 -31.00   0.50    0.20    --  -57.30   0.00 120.00   52
 11  ω      2.00  29.00   0.50    0.20    --   -4.00  34.00 165.74   54
 12  ω      2.00  28.00   0.50    0.20    --   -4.00  33.00  22.86   52
 13  ω      1.00  27.00   0.50    0.20    --   -4.00  33.00 -15.26   52
 14  ω      1.00  26.00   0.50    0.20    --   -4.00  34.00 -78.57   50
 15  ω    -55.00 -28.00   0.50    0.20    --  -44.00 -24.00 103.69   54
 16  ω    -48.00 -19.00   0.50    0.20    --  -28.00 -26.00 161.42   58
 17  ω    -55.00 -29.00   0.50    0.20    --  -57.30 136.00  27.00   52
 18  ω    -86.00 -60.00   0.50    0.20    --  -57.30 136.00  27.00   52
 19  ω    -56.00 -31.00   0.50    0.20    --  -44.00 -24.00  61.23   50
 20  ω    -45.00 -19.00   0.50    0.20    --  -28.00 -26.00-120.86   52
 21  ω    -44.00 -19.00   0.50    0.20    --  -24.00 -27.00 -86.95   50
 22  ω    -51.00 -26.00   0.50    0.20    --  -36.00 -25.00 -54.53   50
 23  ω    -62.00 -35.00   0.50    0.20    --  -52.00 -23.00 -40.57   54
 24  ω    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00 -94.49   50
 25  ω    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00-138.97   50
 26  ω    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00 -13.51   50
 27  ω    -70.00 -44.00   0.50    0.20    --  -64.50 -22.00   1.31   52
 28  ω    -71.00 -45.00   0.50    0.20    --  -64.50 -22.00  30.62   52
 29  ω    -61.00 -35.00   0.50    0.20    --  -52.00 -23.00  80.17   52
 30  ω     44.00  86.00   0.50    0.20    --   67.73  21.00 -51.35   84
 31  ω     46.00  74.00   0.50    0.20    --   67.73  21.00 -82.10   56
 32  ω     52.00 118.00   0.50    0.20    --   81.25  20.00-160.57  132
 33  ω     52.00 130.00   0.50    0.20    --   81.25  20.00 -98.66  156
 34  ω     39.00  90.00   0.50    0.20    --   67.73  20.00  -4.35  102
 35  ω     90.00 127.00   0.50    0.20    --   81.25  20.00  39.35   74
 36  ω     52.00  84.00   0.50    0.20    --   81.25  20.00  39.35   64
 37  ω     43.00  86.00   0.50    0.20    --   75.00  15.00   0.00   86
 38  ω     40.00  77.00   0.50    0.20    --   67.73  20.00  81.75   74
 39  ω     54.00 122.00   0.50    0.20    --   81.25  20.00  97.27  136
 40  ω     98.00 123.00   0.50    0.20    --   81.25  18.00 176.71   50
 41  ω     47.00  74.00   0.50    0.20    --   81.25  18.00 176.71   54
 42  ω     89.00 122.00   0.50    0.20    --   75.00  15.00   0.00   66
 43  ω     67.00 117.00   0.50    0.20    --   77.04   0.00   0.00  100
 44  ω     38.00  63.00   0.50    0.20    --   77.04   0.00   0.00   50
 45  ω     38.00  64.00   0.50    0.20    --   77.04   0.00  90.00   52
 46  ω     74.00 117.00   0.50    0.20    --   77.04   0.00  90.00   86
 47  ω     38.00  63.00   0.50    0.20    --   77.04   0.00 -90.00   50
 48  ω     67.00 113.00   0.50    0.20    --   77.04   0.00 -90.00   92
 49  ω     38.00 116.00   0.50    0.20    --   77.04   0.00-180.00  156
 50  ω     31.00  56.00   0.50    0.20    --   76.00 -56.00 -84.07   50
 51  ω     87.00 114.00   0.50    0.20    --   81.25-129.00-135.38   54
 52  ω     37.00  79.00   0.50    0.20    --   81.25-129.00-135.38   84
 53  ω     35.00  66.00   0.50    0.20    --   77.04-125.00 -90.00   62
 54  ω     52.00 106.00   0.50    0.20    --   77.04-136.00 -36.00  108
 55  ω     71.00 106.00   0.50    0.20    --   75.00-125.00-150.00   70
 56  ω     35.00  63.00   0.50    0.20    --   75.00-125.00-150.00   56
 57  ω     78.00 103.00   0.50    0.20    --   75.00-125.00  30.00   50
 58  ω     35.00  96.00   0.50    0.20    --   77.04-125.00  90.00  122
 59  ω     40.00  75.00   0.50    0.20    --   77.04-125.00 120.00   70
 60  ω     43.00  71.00   0.50    0.20    --   77.04-132.00 140.00   56
 61  ω     83.00 112.00   0.50    0.20    --   77.04-132.00 140.00   58
 62  ω     63.00  88.00   0.50    0.20    --   77.04-125.00   0.00   50
 63  ω     35.00  61.00   0.50    0.20    --   77.04-125.00   0.00   52
 64  ω     37.00  63.00   0.50    0.20    --   75.00-125.00  30.00   52
 65  ω     69.00 110.00   0.50    0.20    --   81.25-123.00 -71.66   82
 66  ω     40.00  90.00   0.50    0.20    --   75.00-125.00-120.00  100
 67  ω     37.00  65.00   0.50    0.20    --   81.25-115.00 -96.61   56
 68  ω     35.00  61.00   0.50    0.20    --   81.25-123.00 -71.66   52
 69  ω     56.00  82.00   0.50    0.20    --   77.04 -94.00-150.00   52
 70  ω     39.00  64.00   0.50    0.20    --   77.04 -94.00   0.00   50
 71  ω     36.00 109.00   0.50    0.20    --   81.25-118.00  48.38  146
 72  ω     38.00 104.00   0.50    0.20    --   81.25-123.00 160.20  132
 73  ω     35.00  70.00   0.50    0.20    --   75.00 -94.00 150.00   70
 74  ω     27.00  53.00   0.50    0.20    --   60.47 -94.00 120.00   52
 75  ω     23.00  52.00   0.50    0.20    --   60.47 -94.00  60.00   58
 76  ω     23.00  54.00   0.50    0.20    --   60.47 -94.00 -60.00   62
 77  ω     45.00  70.00   0.50    0.20    --   81.25 -64.00 -73.32   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0168059000
_diffrn_orient_matrix_UB_12      -0.0400042000
_diffrn_orient_matrix_UB_13      0.1287474000
_diffrn_orient_matrix_UB_21      0.0642151000
_diffrn_orient_matrix_UB_22      0.1270633000
_diffrn_orient_matrix_UB_23      -0.0106524000
_diffrn_orient_matrix_UB_31      -0.1986328000
_diffrn_orient_matrix_UB_32      0.0522520000
_diffrn_orient_matrix_UB_33      0.0016886000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3989
_reflns_number_total             4059
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4059
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.053
_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)+(0.0300P)²+0.6283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.92064(2) 0.18549(2) 0.05563(2) 0.02906(7) Uani 1 1 d . . . . .
O1 O 0.58643(14) 0.78879(10) -0.05375(8) 0.0226(2) Uani 1 1 d . . . . .
O2 O 0.55020(14) 0.71250(9) 0.13551(8) 0.0197(2) Uani 1 1 d . . . . .
O3 O 0.44698(13) 0.76552(10) 0.34453(8) 0.0201(2) Uani 1 1 d . . . . .
O4 O 0.85736(15) 0.77408(12) 0.45712(9) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.81673(19) 0.34450(13) 0.04945(13) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.7302(2) 0.35975(14) 0.14690(13) 0.0241(3) Uani 1 1 d . . . . .
H2 H 0.718370 0.290961 0.215149 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6609(2) 0.47702(14) 0.14334(12) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.603139 0.489264 0.209849 0.026 Uiso 1 1 calc R U . . .
C4 C 0.67573(18) 0.57712(13) 0.04226(12) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.7620(2) 0.55887(13) -0.05454(12) 0.0200(3) Uani 1 1 d . . . . .
H5 H 0.771463 0.626917 -0.123401 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8344(2) 0.44276(14) -0.05173(13) 0.0218(3) Uani 1 1 d . . . . .
H6 H 0.894854 0.430592 -0.117693 0.026 Uiso 1 1 calc R U . . .
C7 C 0.60036(18) 0.70420(13) 0.03389(12) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.47697(19) 0.83346(13) 0.13908(12) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.407804 0.876450 0.073422 0.021 Uiso 1 1 calc R U . . .
C9 C 0.63388(19) 0.91063(13) 0.13371(12) 0.0198(3) Uani 1 1 d . . . . .
H9A H 0.587173 0.995169 0.130224 0.024 Uiso 1 1 calc R U . . .
H9B H 0.718866 0.918081 0.065107 0.024 Uiso 1 1 calc R U . . .
C10 C 0.73399(19) 0.84961(14) 0.23696(12) 0.0201(3) Uani 1 1 d . . . . .
H10A H 0.830364 0.903821 0.235126 0.024 Uiso 1 1 calc R U . . .
H10B H 0.793253 0.769639 0.234836 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6065(2) 0.82612(14) 0.34628(12) 0.0212(3) Uani 1 1 d . . . . .
C12 C 0.34804(19) 0.81003(13) 0.24780(11) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.2313(2) 0.92922(14) 0.24063(13) 0.0235(3) Uani 1 1 d . . . . .
H13A H 0.158004 0.918276 0.312959 0.035 Uiso 1 1 calc R U . . .
H13B H 0.150783 0.947008 0.182218 0.035 Uiso 1 1 calc R U . . .
H13C H 0.310324 0.998552 0.222141 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2228(2) 0.70570(14) 0.26726(13) 0.0229(3) Uani 1 1 d . . . . .
H14A H 0.295059 0.627222 0.279403 0.034 Uiso 1 1 calc R U . . .
H14B H 0.158206 0.724052 0.201484 0.034 Uiso 1 1 calc R U . . .
H14C H 0.134587 0.698726 0.333408 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5591(2) 0.94579(17) 0.37217(15) 0.0322(4) Uani 1 1 d . . . . .
H15A H 0.529450 1.013318 0.303901 0.048 Uiso 1 1 calc R U . . .
H15B H 0.663260 0.967125 0.399278 0.048 Uiso 1 1 calc R U . . .
H15C H 0.454160 0.933617 0.429923 0.048 Uiso 1 1 calc R U . . .
C16 C 0.6971(2) 0.72544(16) 0.44174(13) 0.0286(3) Uani 1 1 d . . . . .
H16 H 0.734222 0.651754 0.418392 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5819(3) 0.6816(2) 0.55653(14) 0.0438(5) Uani 1 1 d . . . . .
H17A H 0.461069 0.726320 0.553125 0.053 Uiso 1 1 calc R U . . .
H17B H 0.564869 0.591290 0.581987 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6891(3) 0.7114(2) 0.63420(15) 0.0404(4) Uani 1 1 d . . . . .
H18A H 0.686791 0.642677 0.707350 0.049 Uiso 1 1 calc R U . . .
H18B H 0.638246 0.788441 0.647122 0.049 Uiso 1 1 calc R U . . .
C19 C 0.8825(2) 0.72836(16) 0.57475(13) 0.0272(3) Uani 1 1 d . . . . .
C20 C 0.9965(3) 0.60676(19) 0.60119(17) 0.0413(4) Uani 1 1 d . . . . .
H20A H 0.932135 0.545051 0.586556 0.062 Uiso 1 1 calc R U . . .
H20B H 1.017173 0.576562 0.680272 0.062 Uiso 1 1 calc R U . . .
H20C H 1.113507 0.620267 0.553780 0.062 Uiso 1 1 calc R U . . .
C21 C 0.9789(3) 0.82669(19) 0.59507(18) 0.0440(5) Uani 1 1 d . . . . .
H21A H 1.099641 0.836221 0.551762 0.066 Uiso 1 1 calc R U . . .
H21B H 0.991643 0.801489 0.675087 0.066 Uiso 1 1 calc R U . . .
H21C H 0.907898 0.905933 0.571503 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.8980(15) . ?
O1 C7 1.2093(18) . ?
O2 C7 1.3395(17) . ?
O2 C8 1.4608(16) . ?
O3 C11 1.4435(17) . ?
O3 C12 1.4445(16) . ?
O4 C16 1.4343(18) . ?
O4 C19 1.4466(18) . ?
C1 C2 1.384(2) . ?
C1 C6 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.4892(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.5169(19) . ?
C8 C12 1.5297(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5258(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.530(2) . ?
C11 C15 1.529(2) . ?
C11 C16 1.542(2) . ?
C12 C13 1.533(2) . ?
C12 C14 1.5235(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.535(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.510(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.525(2) . ?
C19 C20 1.520(3) . ?
C19 C21 1.516(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C7 O2 C8 116.89(11) . . ?
C11 O3 C12 120.42(10) . . ?
C16 O4 C19 109.87(11) . . ?
C2 C1 Br1 118.94(11) . . ?
C2 C1 C6 121.91(14) . . ?
C6 C1 Br1 119.11(11) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.95(14) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.15(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C7 122.07(13) . . ?
C5 C4 C3 119.66(13) . . ?
C5 C4 C7 118.27(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.76(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.57(14) . . ?
C5 C6 H6 120.7 . . ?
O1 C7 O2 124.56(13) . . ?
O1 C7 C4 124.05(13) . . ?
O2 C7 C4 111.39(12) . . ?
O2 C8 H8 109.5 . . ?
O2 C8 C9 108.68(11) . . ?
O2 C8 C12 107.31(11) . . ?
C9 C8 H8 109.5 . . ?
C9 C8 C12 112.26(12) . . ?
C12 C8 H8 109.5 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.98(11) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.22(12) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
O3 C11 C10 111.15(11) . . ?
O3 C11 C15 112.41(12) . . ?
O3 C11 C16 101.27(11) . . ?
C10 C11 C16 108.76(12) . . ?
C15 C11 C10 111.27(13) . . ?
C15 C11 C16 111.53(13) . . ?
O3 C12 C8 111.19(11) . . ?
O3 C12 C13 112.76(12) . . ?
O3 C12 C14 103.61(11) . . ?
C8 C12 C13 108.81(11) . . ?
C14 C12 C8 111.74(12) . . ?
C14 C12 C13 108.68(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C11 108.16(12) . . ?
O4 C16 H16 108.5 . . ?
O4 C16 C17 106.74(13) . . ?
C11 C16 H16 108.5 . . ?
C17 C16 C11 116.19(15) . . ?
C17 C16 H16 108.5 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 C16 104.79(14) . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C17 C18 C19 105.46(14) . . ?
H18A C18 H18B 108.8 . . ?
C19 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
O4 C19 C18 103.56(13) . . ?
O4 C19 C20 109.05(14) . . ?
O4 C19 C21 106.97(14) . . ?
C20 C19 C18 112.47(16) . . ?
C21 C19 C18 113.35(16) . . ?
C21 C19 C20 110.95(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Br1 C1 C2 C3 177.35(11) . . . . ?
Br1 C1 C6 C5 -178.39(10) . . . . ?
O2 C8 C9 C10 -63.60(14) . . . . ?
O2 C8 C12 O3 70.02(14) . . . . ?
O2 C8 C12 C13 -165.21(11) . . . . ?
O2 C8 C12 C14 -45.21(15) . . . . ?
O3 C11 C16 O4 -177.86(12) . . . . ?
O3 C11 C16 C17 -57.92(18) . . . . ?
O4 C16 C17 C18 0.8(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C4 C7 178.83(13) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C7 O1 -168.71(14) . . . . ?
C3 C4 C7 O2 11.24(18) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C5 C4 C7 O1 10.8(2) . . . . ?
C5 C4 C7 O2 -169.24(12) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C7 O2 C8 C9 -85.95(14) . . . . ?
C7 O2 C8 C12 152.44(11) . . . . ?
C7 C4 C5 C6 -179.92(13) . . . . ?
C8 O2 C7 O1 -1.2(2) . . . . ?
C8 O2 C7 C4 178.87(11) . . . . ?
C8 C9 C10 C11 -54.84(16) . . . . ?
C9 C8 C12 O3 -49.32(15) . . . . ?
C9 C8 C12 C13 75.45(14) . . . . ?
C9 C8 C12 C14 -164.55(12) . . . . ?
C9 C10 C11 O3 49.02(16) . . . . ?
C9 C10 C11 C15 -77.07(16) . . . . ?
C9 C10 C11 C16 159.68(12) . . . . ?
C10 C11 C16 O4 65.00(16) . . . . ?
C10 C11 C16 C17 -175.06(14) . . . . ?
C11 O3 C12 C8 46.70(16) . . . . ?
C11 O3 C12 C13 -75.81(15) . . . . ?
C11 O3 C12 C14 166.87(12) . . . . ?
C11 C16 C17 C18 -119.92(18) . . . . ?
C12 O3 C11 C10 -46.62(17) . . . . ?
C12 O3 C11 C15 78.85(16) . . . . ?
C12 O3 C11 C16 -162.01(12) . . . . ?
C12 C8 C9 C10 54.94(15) . . . . ?
C15 C11 C16 O4 -58.09(17) . . . . ?
C15 C11 C16 C17 61.85(19) . . . . ?
C16 O4 C19 C18 -30.44(18) . . . . ?
C16 O4 C19 C20 89.51(17) . . . . ?
C16 O4 C19 C21 -150.43(15) . . . . ?
C16 C17 C18 C19 -18.7(2) . . . . ?
C17 C18 C19 O4 29.8(2) . . . . ?
C17 C18 C19 C20 -87.81(19) . . . . ?
C17 C18 C19 C21 145.30(17) . . . . ?
C19 O4 C16 C11 144.61(14) . . . . ?
C19 O4 C16 C17 18.91(19) . . . . ?

_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 1.809
_oxdiff_exptl_absorpt_empirical_full_min 0.515
