# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_she18_10sn
_database_code_depnum_ccdc_archive 'CCDC 1902661'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;The Australian National University
Australia
;
# publcif _publ_body_element loop end

_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 1'
_publcif_datablock.id            {889f31d6-380d-432e-ac66-f7cb83b3d73b}

#
# add machine specifics from crysalis pro
# ban16_pc38sn_scaled.cif
#
_audit_creation_date             2018-02-09
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_cell_length_a                   9.6214(3)
_cell_length_b                   10.8141(3)
_cell_length_c                   15.9731(5)
_cell_angle_alpha                76.964(3)
_cell_angle_beta                 79.006(3)
_cell_angle_gamma                64.023(3)
_cell_volume                     1447.50(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    14713
_cell_measurement_theta_min      4.9940
_cell_measurement_theta_max      73.4650
#
# skip _cell_oxdiff_length_a  etc
#
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.092
#
# add _exptl_crystal_description manually if not present
#
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
#
# skip _exptl_crystal_face_index_h etc
#
_exptl_absorpt_correction_T_min  0.68216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#
# skip _oxdiff_exptl_absorpt_empirical_full_min   etc
#
_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1297
_diffrn_reflns_number            29490
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.6085
_diffrn_reflns_theta_max         73.6842
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_reflns_theta_full        74.3338
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1312224000
_diffrn_orient_matrix_UB_12      -0.1358880000
_diffrn_orient_matrix_UB_13      0.0371924000
_diffrn_orient_matrix_UB_21      0.0731299000
_diffrn_orient_matrix_UB_22      -0.0268625000
_diffrn_orient_matrix_UB_23      -0.0923393000
_diffrn_orient_matrix_UB_31      0.0975226000
_diffrn_orient_matrix_UB_32      0.0811972000
_diffrn_orient_matrix_UB_33      0.0000124000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  31.00   1.00    1.00    --  -37.04  77.00  60.00   95
  2  ω     29.00  96.00   1.00    1.00    --   37.04-135.00  78.00   67
  3  ω     23.00  90.00   1.00    1.00    --   37.04-125.00 -90.00   67
  4  ω    -34.00  66.00   1.00    1.00    --   37.04 -19.00 -60.00  100
  5  ω    -31.00  64.00   1.00    1.00    --   37.04 -77.00 -60.00   95
  6  ω    -31.00  64.00   1.00    1.00    --   37.04 -77.00 -90.00   95
  7  ω     23.00  90.00   1.00    1.00    --   37.04-125.00-150.00   67
  8  ω     23.00  90.00   1.00    1.00    --   37.04-125.00-120.00   67
  9  ω     20.00 104.00   1.00    1.00    --   37.04  57.00 -30.00   84
 10  ω    -34.00  66.00   1.00    1.00    --   37.04 -19.00 150.00  100
 11  ω     10.00 105.00   1.00    1.00    --   37.04  77.00  90.00   95
 12  ω      1.00  76.00   1.00    1.00    --   37.04 -99.00 150.00   75
 13  ω     92.00 178.00   1.00    1.41    --  111.00  38.00-120.00   86
 14  ω     44.00 131.00   1.00    1.41    --  111.00 -64.00 120.00   87
 15  ω     42.00 130.00   1.00    1.41    --  111.00 -38.00-120.00   88
 16  ω     41.00 116.00   1.00    1.41    --  111.00-111.00 -60.00   75
 17  ω     43.00 138.00   1.00    1.41    --  111.00 -77.00-180.00   95
 18  ω    100.00 178.00   1.00    1.41    --  111.00 111.00 -30.00   78
 19  ω     84.00 178.00   1.00    1.41    --  111.00  77.00  30.00   94
 20  ω     43.00 138.00   1.00    1.41    --  111.00 -77.00  90.00   95
 21  ω     41.00 116.00   1.00    1.41    --  111.00-111.00 120.00   75
 22  ω     43.00 138.00   1.00    1.41    --  111.00 -77.00 -30.00   95
 23  ω     43.00 128.00   1.00    1.41    --  111.00 -50.00 -60.00   85
 24  ω     43.00 128.00   1.00    1.41    --  111.00 -50.00  60.00   85
 25  ω     65.00 178.00   1.00    1.41    --  111.00  12.00 -60.00  113
 26  ω     41.00 116.00   1.00    1.41    --  111.00-111.00  90.00   75
 27  ω     41.00 157.00   1.00    1.41    --  111.00 -12.00-120.00  116
 28  ω     94.00 178.00   1.00    1.41    --  111.00  50.00-180.00   84
 29  ω     44.00 131.00   1.00    1.41    --  111.00 -64.00  60.00   87
 30  ω     57.00 150.00   1.00    1.41    --  111.00 178.00 -30.00   93
 31  ω     94.00 178.00   1.00    1.41    --  111.00  50.00 150.00   84
 32  ω     43.00 138.00   1.00    1.41    --  111.00 -77.00 -90.00   95
 33  ω     43.00 126.00   1.00    1.41    --  111.00-135.00  78.00   83
 34  ω     42.00 130.00   1.00    1.41    --  111.00 -38.00  60.00   88
 35  ω     84.00 178.00   1.00    1.41    --  111.00  77.00 -60.00   94
 36  ω     84.00 178.00   1.00    1.41    --  111.00  77.00   0.00   94
 37  ω     41.00 116.00   1.00    1.41    --  111.00-111.00 -90.00   75
 38  ω     44.00 131.00   1.00    1.41    --  111.00 -64.00-150.00   87
 39  ω     41.00 116.00   1.00    1.41    --  111.00-111.00-180.00   75
 40  ω    100.00 178.00   1.00    1.41    --  111.00 111.00   0.00   78
 41  ω     92.00 178.00   1.00    1.41    --  111.00  38.00-180.00   86
 42  ω     91.00 178.00   1.00    1.41    --  111.00  64.00 -60.00   87
 43  ω     91.00 178.00   1.00    1.41    --  111.00  64.00  60.00   87
 44  ω     92.00 178.00   1.00    1.41    --  111.00  38.00 120.00   86
 45  ω     10.00 105.00   1.00    1.00    --   37.04  77.00-150.00   95
 46  ω     20.00 104.00   1.00    1.00    --   37.04  57.00  30.00   84
 47  ω     18.00 106.00   1.00    1.00    --   37.04  38.00 -30.00   88
 48  ω     20.00 104.00   1.00    1.00    --   37.04  57.00-180.00   84
 49  ω      1.00  27.00   1.00    1.00    --   37.04  93.00-111.18   26
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_space_group_IT_number           2
_space_group_crystal_system      triclinic
#
# skip intenisty data and ins header
# finished with crysalis pro cif file
#
#------------------------------------------------------------------------
#
# data from SHELX
#
# skip first few lines
#
_chemical_formula_sum            'C18 H15 Br'
_chemical_formula_weight         311.21

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'
#
# already have cell_setting and H-M space group so skip
#
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
#
# skip some lines we already have
#
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    3.711
#
# skip some more
#
_reflns_number_total             5613
_reflns_number_gt                5389
_reflns_threshold_expression     >2sigma(I)
#
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015)'
#
# add graphics and publication software to keep publcif happy
#
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_molecular_graphics    'SHELXLE (C. B. HÃ1/4bschle et al.,2011)'
#
# rest of shelx cif file 
#
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+20.3749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5613
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.2290
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2017(10) 1.2014(10) 0.8603(6) 0.048(2) Uani 1 1 d . . .
H1 H 0.2985 1.1870 0.8265 0.057 Uiso 1 1 calc R . .
C2 C 0.1321(13) 1.3082(10) 0.9079(7) 0.055(2) Uani 1 1 d . . .
H2 H 0.1840 1.3660 0.9067 0.066 Uiso 1 1 calc R . .
C3 C -0.0042(12) 1.3352(11) 0.9558(7) 0.055(2) Uani 1 1 d . . .
H3 H -0.0494 1.4107 0.9875 0.066 Uiso 1 1 calc R . .
C4 C -0.0762(12) 1.2510(9) 0.9579(6) 0.049(2) Uani 1 1 d . . .
H4 H -0.1739 1.2700 0.9915 0.058 Uiso 1 1 calc R . .
C5 C -0.0165(10) 1.1416(9) 0.9147(6) 0.0416(19) Uani 1 1 d . . .
H5 H -0.0707 1.0846 0.9197 0.050 Uiso 1 1 calc R . .
C6 C 0.1262(12) 1.1122(10) 0.8623(6) 0.049(2) Uani 1 1 d . . .
C8 C 0.1527(12) 0.8976(11) 0.8122(6) 0.052(2) Uani 1 1 d . . .
H8 H 0.0563 0.9032 0.8435 0.062 Uiso 1 1 calc R . .
C7 C 0.2027(10) 0.9940(10) 0.8148(6) 0.047(2) Uani 1 1 d . . .
H7 H 0.2992 0.9849 0.7820 0.057 Uiso 1 1 calc R . .
C9 C 0.2399(11) 0.7868(11) 0.7638(6) 0.051(2) Uani 1 1 d . . .
H9 H 0.3381 0.7829 0.7361 0.062 Uiso 1 1 calc R . .
C11 C 0.3002(9) 0.5776(10) 0.6988(6) 0.0430(19) Uani 1 1 d . . .
H11 H 0.3967 0.5787 0.6718 0.052 Uiso 1 1 calc R . .
C10 C 0.2018(10) 0.6891(11) 0.7525(6) 0.048(2) Uani 1 1 d . . .
C12 C 0.2678(11) 0.4792(10) 0.6851(6) 0.049(2) Uani 1 1 d . . .
H12 H 0.1724 0.4761 0.7124 0.059 Uiso 1 1 calc R . .
C13 C 0.3678(11) 0.3716(10) 0.6302(6) 0.047(2) Uani 1 1 d . . .
C14 C 0.3177(11) 0.2748(10) 0.6235(7) 0.054(2) Uani 1 1 d . . .
H14 H 0.2228 0.2774 0.6555 0.065 Uiso 1 1 calc R . .
C15 C 0.3983(13) 0.1738(12) 0.5725(10) 0.077(4) Uani 1 1 d . . .
H15 H 0.3583 0.1091 0.5690 0.092 Uiso 1 1 calc R . .
C16 C 0.5430(13) 0.1659(13) 0.5246(9) 0.076(4) Uani 1 1 d . . .
H16 H 0.6012 0.0977 0.4882 0.092 Uiso 1 1 calc R . .
C17 C 0.5940(11) 0.2647(11) 0.5345(6) 0.053(2) Uani 1 1 d . . .
H17 H 0.6908 0.2629 0.5058 0.064 Uiso 1 1 calc R . .
C18 C 0.5037(12) 0.3644(10) 0.5859(6) 0.053(2) Uani 1 1 d . . .
H18 H 0.5395 0.4316 0.5902 0.063 Uiso 1 1 calc R . .
Br19 Br 0.00893(11) 0.68501(11) 0.80579(7) 0.0506(3) Uani 1 1 d . . .
C20 C 0.6119(9) 0.0917(9) -0.0285(5) 0.0386(18) Uani 1 1 d . . .
H20 H 0.6100 0.0545 0.0314 0.046 Uiso 1 1 calc R . .
C21 C 0.6875(10) 0.0024(9) -0.0890(6) 0.044(2) Uani 1 1 d . . .
H21 H 0.7354 -0.0954 -0.0705 0.053 Uiso 1 1 calc R . .
C22 C 0.6929(10) 0.0564(11) -0.1768(6) 0.047(2) Uani 1 1 d . . .
H22 H 0.7447 -0.0043 -0.2183 0.056 Uiso 1 1 calc R . .
C23 C 0.6259(9) 0.1917(10) -0.2018(5) 0.0364(18) Uani 1 1 d . . .
H23 H 0.6298 0.2266 -0.2620 0.044 Uiso 1 1 calc R . .
C24 C 0.5484(10) 0.2878(10) -0.1437(5) 0.0423(19) Uani 1 1 d . . .
H24 H 0.5039 0.3853 -0.1640 0.051 Uiso 1 1 calc R . .
C25 C 0.5390(8) 0.2353(9) -0.0549(5) 0.0330(16) Uani 1 1 d . . .
C26 C 0.4563(10) 0.3333(9) 0.0067(5) 0.0393(18) Uani 1 1 d . . .
H26 H 0.4203 0.4297 -0.0163 0.047 Uiso 1 1 calc R . .
C27 C 0.4265(9) 0.2996(9) 0.0930(5) 0.0385(18) Uani 1 1 d . . .
H27 H 0.4595 0.2045 0.1189 0.046 Uiso 1 1 calc R . .
C28 C 0.3438(10) 0.4088(9) 0.1463(5) 0.0388(17) Uani 1 1 d . . .
H28 H 0.3140 0.5015 0.1161 0.047 Uiso 1 1 calc R . .
C29 C 0.3038(10) 0.3969(9) 0.2321(5) 0.0395(18) Uani 1 1 d . . .
C30 C 0.2208(9) 0.5157(9) 0.2765(5) 0.0361(17) Uani 1 1 d . . .
H30 H 0.1866 0.6043 0.2407 0.043 Uiso 1 1 calc R . .
C31 C 0.1859(9) 0.5168(9) 0.3614(5) 0.0369(17) Uani 1 1 d . . .
H31 H 0.2168 0.4290 0.3982 0.044 Uiso 1 1 calc R . .
C32 C 0.1044(9) 0.6411(9) 0.4031(5) 0.0395(18) Uani 1 1 d . . .
C33 C 0.0498(10) 0.7756(9) 0.3590(5) 0.0400(18) Uani 1 1 d . . .
H33 H 0.0653 0.7914 0.2976 0.048 Uiso 1 1 calc R . .
C34 C -0.0284(10) 0.8890(9) 0.4035(6) 0.045(2) Uani 1 1 d . . .
H34 H -0.0639 0.9813 0.3723 0.054 Uiso 1 1 calc R . .
C35 C -0.0540(10) 0.8674(9) 0.4924(6) 0.0430(19) Uani 1 1 d . . .
H35 H -0.1085 0.9445 0.5225 0.052 Uiso 1 1 calc R . .
C36 C -0.0004(10) 0.7341(10) 0.5371(5) 0.0409(19) Uani 1 1 d . . .
H36 H -0.0168 0.7189 0.5984 0.049 Uiso 1 1 calc R . .
C37 C 0.0775(9) 0.6214(9) 0.4932(5) 0.0384(17) Uani 1 1 d . . .
H37 H 0.1132 0.5295 0.5249 0.046 Uiso 1 1 calc R . .
Br38 Br 0.36116(10) 0.21529(9) 0.30077(6) 0.0420(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(14) . ?
C1 C6 1.433(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.332(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.352(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.466(13) . ?
C8 C7 1.337(13) . ?
C8 C9 1.424(15) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.318(14) . ?
C9 H9 0.9500 . ?
C11 C12 1.304(13) . ?
C11 C10 1.498(13) . ?
C11 H11 0.9500 . ?
C10 Br19 1.903(9) . ?
C12 C13 1.485(13) . ?
C12 H12 0.9500 . ?
C13 C18 1.341(14) . ?
C13 C14 1.361(13) . ?
C14 C15 1.369(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.432(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(13) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 C21 1.391(12) . ?
C20 C25 1.395(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(13) . ?
C21 H21 0.9500 . ?
C22 C23 1.313(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.411(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.406(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.469(11) . ?
C26 C27 1.351(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.458(11) . ?
C27 H27 0.9500 . ?
C28 C29 1.345(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.444(11) . ?
C29 Br38 1.916(9) . ?
C30 C31 1.336(11) . ?
C30 H30 0.9500 . ?
C31 C32 1.465(12) . ?
C31 H31 0.9500 . ?
C32 C33 1.378(12) . ?
C32 C37 1.397(11) . ?
C33 C34 1.399(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.371(13) . ?
C35 H35 0.9500 . ?
C36 C37 1.387(12) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.0(9) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C3 C2 C1 123.5(9) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 117.7(10) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 123.6(10) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C6 120.0(9) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 116.2(8) . . ?
C5 C6 C7 124.2(9) . . ?
C1 C6 C7 119.5(9) . . ?
C7 C8 C9 121.8(10) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C7 C6 127.6(9) . . ?
C8 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C10 C9 C8 128.2(9) . . ?
C10 C9 H9 115.9 . . ?
C8 C9 H9 115.9 . . ?
C12 C11 C10 127.0(8) . . ?
C12 C11 H11 116.5 . . ?
C10 C11 H11 116.5 . . ?
C9 C10 C11 124.5(8) . . ?
C9 C10 Br19 119.7(8) . . ?
C11 C10 Br19 115.8(7) . . ?
C11 C12 C13 125.4(9) . . ?
C11 C12 H12 117.3 . . ?
C13 C12 H12 117.3 . . ?
C18 C13 C14 117.7(9) . . ?
C18 C13 C12 124.3(9) . . ?
C14 C13 C12 118.0(9) . . ?
C13 C14 C15 122.8(10) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C14 C15 C16 119.8(10) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 116.2(9) . . ?
C17 C16 H16 121.9 . . ?
C15 C16 H16 121.9 . . ?
C18 C17 C16 120.0(10) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C13 C18 C17 123.5(10) . . ?
C13 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C21 C20 C25 120.6(8) . . ?
C21 C20 H20 119.7 . . ?
C25 C20 H20 119.7 . . ?
C20 C21 C22 120.0(8) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.6(8) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 123.2(8) . . ?
C22 C23 H23 118.4 . . ?
C24 C23 H23 118.4 . . ?
C25 C24 C23 118.1(8) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C20 C25 C24 118.5(7) . . ?
C20 C25 C26 122.4(7) . . ?
C24 C25 C26 119.1(8) . . ?
C27 C26 C25 126.4(8) . . ?
C27 C26 H26 116.8 . . ?
C25 C26 H26 116.8 . . ?
C26 C27 C28 120.2(8) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 129.1(8) . . ?
C29 C28 H28 115.4 . . ?
C27 C28 H28 115.4 . . ?
C28 C29 C30 123.0(8) . . ?
C28 C29 Br38 119.5(7) . . ?
C30 C29 Br38 117.5(6) . . ?
C31 C30 C29 128.3(8) . . ?
C31 C30 H30 115.9 . . ?
C29 C30 H30 115.9 . . ?
C30 C31 C32 126.0(8) . . ?
C30 C31 H31 117.0 . . ?
C32 C31 H31 117.0 . . ?
C33 C32 C37 118.1(8) . . ?
C33 C32 C31 124.1(8) . . ?
C37 C32 C31 117.8(8) . . ?
C32 C33 C34 120.7(8) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 120.2(8) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 119.6(8) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 120.3(8) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C32 121.0(8) . . ?
C36 C37 H37 119.5 . . ?
C32 C37 H37 119.5 . . ?

_refine_diff_density_max         1.825
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.144
####################################################################### 
# 
# 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_she18_05sn_scaled
_database_code_depnum_ccdc_archive 'CCDC 1902662'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;The Australian National University
Australia
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18'
_chemical_formula_sum            'C21 H18'
_chemical_formula_weight         270.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.9002(3)
_cell_length_b                   20.0267(4)
_cell_length_c                   7.63560(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1666.81(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4184
_cell_measurement_temperature    293.80(17)
_cell_measurement_theta_max      70.6420
_cell_measurement_theta_min      4.0730
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.077
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 13 0.0968
-1 0 -13 0.0666
2 0 -12 0.0786
1 0 13 0.0953
-7 0 -1 0.1997
1 -5 0 0.1830
7 0 1 0.2275
1 5 0 0.1301
-1 5 0 0.1463
1 -2 12 0.1212
-1 -2 12 0.1247
-4 1 10 0.1602
0 2 12 0.0948
-4 1 10 0.1426

_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.166
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
-1.1483 -0.3880 12.7866 -0.2311 -0.9658 0.1176
-1.2952 0.3519 -12.7471 0.2259 0.9472 0.2274
2.4119 0.3884 -12.1776 0.2225 0.9282 -0.2981
0.5262 -0.3681 12.9280 -0.2306 -0.9657 -0.1195
-7.0652 0.0999 -0.5902 0.0343 -0.0067 0.9994
1.3740 -4.8600 0.4686 -0.9751 0.1278 -0.1810
7.0649 0.1173 0.5744 0.0092 0.0010 -1.0000
1.1734 4.8876 -0.2604 0.9755 -0.1270 -0.1795
-1.0000 5.0000 0.0000 0.9970 -0.1652 0.1261
1.0000 -2.0000 12.0000 -0.5449 -0.8403 -0.1781
-1.0000 -2.0000 12.0000 -0.5428 -0.8540 0.1043
-4.0000 1.0000 10.0000 0.0821 -0.8178 0.5260
-0.0000 2.0000 12.0000 0.2529 -0.9739 -0.0490
-4.0000 1.0000 10.0000 0.0821 -0.8178 0.5260

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8784
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.717
_diffrn_reflns_theta_min         4.416
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.80(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -36.03 -57.00 -90.00   84
  2  ω    -33.00  55.00   1.00    1.00    --   36.03 -38.00  90.00   88
  3  ω     23.00  89.00   1.00    1.00    --   36.03-125.00 -90.00   66
  4  ω     91.00 176.00   1.00   11.07    --  108.91  61.00  30.00   85
  5  ω     82.00 176.00   1.00   11.07    --  108.91  77.00 120.00   94
  6  ω     39.00 110.00   1.00   11.07    --  108.91 -95.00 -90.00   71
  7  ω    100.00 178.00   1.00   11.07    --  108.91 111.00 150.00   78
  8  ω   -104.00  -9.00   1.00    1.00    --  -36.03 -77.00 150.00   95
  9  ω   -103.00 -19.00   1.00    1.00    --  -36.03 -57.00  30.00   84
 10  ω     71.00 178.00   1.00   11.07    --  108.91  15.00 -60.00  107
 11  ω     91.00 176.00   1.00   11.07    --  108.91  61.00-150.00   85
 12  ω     82.00 176.00   1.00   11.07    --  108.91  77.00 -30.00   94
 13  ω     42.00 127.00   1.00   11.07    --  108.91 -61.00  60.00   85
 14  ω    -31.00  39.00   1.00    1.00    --   36.03 -57.00   0.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0010217000
_diffrn_orient_matrix_UB_12      0.1991912000
_diffrn_orient_matrix_UB_13      -0.0121215000
_diffrn_orient_matrix_UB_21      0.0068427000
_diffrn_orient_matrix_UB_22      -0.0316786000
_diffrn_orient_matrix_UB_23      -0.0758787000
_diffrn_orient_matrix_UB_31      -0.1411966000
_diffrn_orient_matrix_UB_32      -0.0030223000
_diffrn_orient_matrix_UB_33      -0.0035791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                2705
_reflns_number_total             3141
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.033
_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)+(0.0948P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1605
_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. Rigid body (RIGU) restrains
 C19A, C19B, C20A, C20B, C21A, C21B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C19B)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21C)=
 Sof(H21D)=1-FVAR(1)
 Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18)
4.b X=CH2 refined with riding coordinates:
 C21A(H21A,H21B), C21B(H21C,H21D)
4.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_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
C1 C 0.5893(3) 0.77887(16) 0.6486(4) 0.0694(8) Uani 1 1 d . . . . .
H1 H 0.5283 0.7539 0.7033 0.083 Uiso 1 1 calc R . . . .
C2 C 0.5819(4) 0.84699(17) 0.6468(5) 0.0826(10) Uani 1 1 d . . . . .
H2 H 0.5160 0.8679 0.7014 0.099 Uiso 1 1 calc R . . . .
C3 C 0.6691(4) 0.88495(15) 0.5667(6) 0.0844(10) Uani 1 1 d . . . . .
H3 H 0.6619 0.9312 0.5651 0.101 Uiso 1 1 calc R . . . .
C4 C 0.7673(4) 0.85474(17) 0.4888(5) 0.0792(9) Uani 1 1 d . . . . .
H4 H 0.8275 0.8804 0.4348 0.095 Uiso 1 1 calc R . . . .
C5 C 0.7770(3) 0.78613(16) 0.4901(4) 0.0683(8) Uani 1 1 d . . . . .
H5 H 0.8445 0.7660 0.4374 0.082 Uiso 1 1 calc R . . . .
C6 C 0.6881(3) 0.74656(12) 0.5686(4) 0.0584(6) Uani 1 1 d . . . . .
C7 C 0.7039(3) 0.67398(13) 0.5594(5) 0.0661(7) Uani 1 1 d . . . . .
H7 H 0.7793 0.6582 0.5198 0.079 Uiso 1 1 calc R . . . .
C8 C 0.6188(3) 0.62802(14) 0.6034(4) 0.0672(7) Uani 1 1 d . . . . .
H8 H 0.5448 0.6434 0.6486 0.081 Uiso 1 1 calc R . . . .
C9 C 0.6339(3) 0.55671(14) 0.5853(5) 0.0717(8) Uani 1 1 d . . . . .
C10 C 0.5420(4) 0.51567(17) 0.6204(6) 0.0855(10) Uani 1 1 d . . . . .
H10 H 0.4693 0.5342 0.6613 0.103 Uiso 1 1 calc R . . . .
C11 C 0.5470(3) 0.44426(15) 0.5997(5) 0.0785(9) Uani 1 1 d . . . . .
C12 C 0.5479(3) 0.38529(16) 0.5855(5) 0.0744(8) Uani 1 1 d . . . . .
C13 C 0.5575(3) 0.31379(13) 0.5755(4) 0.0626(7) Uani 1 1 d . . . . .
C14 C 0.4695(3) 0.27464(16) 0.6549(4) 0.0678(7) Uani 1 1 d . . . . .
H14 H 0.4033 0.2948 0.7106 0.081 Uiso 1 1 calc R . . . .
C15 C 0.4785(4) 0.20688(17) 0.6525(5) 0.0770(9) Uani 1 1 d . . . . .
H15 H 0.4181 0.1811 0.7058 0.092 Uiso 1 1 calc R . . . .
C16 C 0.5754(4) 0.17635(16) 0.5726(5) 0.0806(9) Uani 1 1 d . . . . .
H16 H 0.5823 0.1301 0.5733 0.097 Uiso 1 1 calc R . . . .
C17 C 0.6637(4) 0.2153(2) 0.4901(5) 0.0828(10) Uani 1 1 d . . . . .
H17 H 0.7293 0.1949 0.4336 0.099 Uiso 1 1 calc R . . . .
C18 C 0.6547(3) 0.28310(19) 0.4916(4) 0.0758(9) Uani 1 1 d . . . . .
H18 H 0.7142 0.3088 0.4361 0.091 Uiso 1 1 calc R . . . .
C19A C 0.755(2) 0.5298(11) 0.554(3) 0.092(5) Uani 0.42(3) 1 d . U P A 1
C19B C 0.7515(15) 0.5285(8) 0.5022(18) 0.081(3) Uani 0.58(3) 1 d . U P A 2
C20A C 0.8259(15) 0.5119(10) 0.703(4) 0.113(5) Uani 0.42(3) 1 d . U P A 1
H20A H 0.8312 0.5493 0.7815 0.169 Uiso 0.42(3) 1 calc GR . P A 1
H20B H 0.9069 0.4991 0.6669 0.169 Uiso 0.42(3) 1 calc GR . P A 1
H20C H 0.7874 0.4751 0.7622 0.169 Uiso 0.42(3) 1 calc GR . P A 1
C20B C 0.8412(11) 0.4947(8) 0.611(3) 0.118(4) Uani 0.58(3) 1 d . U P A 2
H20D H 0.8586 0.5214 0.7123 0.176 Uiso 0.58(3) 1 calc GR . P A 2
H20E H 0.9152 0.4879 0.5453 0.176 Uiso 0.58(3) 1 calc GR . P A 2
H20F H 0.8090 0.4523 0.6474 0.176 Uiso 0.58(3) 1 calc GR . P A 2
C21A C 0.795(2) 0.5196(13) 0.387(3) 0.136(7) Uani 0.42(3) 1 d . U P A 1
H21A H 0.8708 0.5001 0.3673 0.163 Uiso 0.42(3) 1 calc R . P A 1
H21B H 0.7455 0.5321 0.2935 0.163 Uiso 0.42(3) 1 calc R . P A 1
C21B C 0.7731(11) 0.5395(5) 0.3338(16) 0.089(3) Uani 0.58(3) 1 d . U P A 2
H21C H 0.8465 0.5254 0.2840 0.106 Uiso 0.58(3) 1 calc R . P A 2
H21D H 0.7149 0.5613 0.2656 0.106 Uiso 0.58(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.367(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.362(5) . ?
C3 C4 1.366(5) . ?
C4 C5 1.378(5) . ?
C5 C6 1.389(4) . ?
C6 C7 1.465(3) . ?
C7 C8 1.350(4) . ?
C8 C9 1.444(4) . ?
C9 C10 1.323(5) . ?
C9 C19A 1.45(2) . ?
C9 C19B 1.538(16) . ?
C10 C11 1.440(4) . ?
C11 C12 1.186(4) . ?
C12 C13 1.438(4) . ?
C13 C14 1.379(4) . ?
C13 C18 1.383(5) . ?
C14 C15 1.361(4) . ?
C15 C16 1.365(5) . ?
C16 C17 1.389(6) . ?
C17 C18 1.362(5) . ?
C19A C20A 1.42(2) . ?
C19A C21A 1.36(3) . ?
C19B C20B 1.451(16) . ?
C19B C21B 1.326(16) . ?

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
C2 C1 C6 120.2(3) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C3 C4 119.7(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C5 C6 121.2(3) . . ?
C1 C6 C7 124.9(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 117.6(3) . . ?
C8 C7 C6 125.7(3) . . ?
C7 C8 C9 124.9(3) . . ?
C8 C9 C19A 119.2(10) . . ?
C8 C9 C19B 119.8(7) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 C19A 119.6(10) . . ?
C10 C9 C19B 119.1(7) . . ?
C9 C10 C11 124.5(4) . . ?
C12 C11 C10 178.0(4) . . ?
C11 C12 C13 175.7(4) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 C18 118.9(3) . . ?
C18 C13 C12 121.5(3) . . ?
C15 C14 C13 120.7(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C17 119.2(3) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C13 120.1(3) . . ?
C20A C19A C9 117.2(17) . . ?
C21A C19A C9 119.9(17) . . ?
C21A C19A C20A 122.9(18) . . ?
C20B C19B C9 119.8(11) . . ?
C21B C19B C9 119.2(11) . . ?
C21B C19B C20B 120.9(14) . . ?

_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_she18_11sn
_database_code_depnum_ccdc_archive 'CCDC 1902663'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;The Australian National University
Australia
;
# publcif _publ_body_element loop end

_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
#Added by publCIF




_symmetry_space_group_name_hall  'P 2ac 2ab'
_publcif_datablock.id            {91481bf8-c914-43ff-8bf4-ade9ae44ccf1}

#
# add machine specifics from crysalis pro
# ban16_pc38sn_scaled.cif
#
_audit_creation_date             2018-02-09
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_cell_length_a                   5.79782(9)
_cell_length_b                   7.59133(14)
_cell_length_c                   63.3743(11)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2789.30(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    15596
_cell_measurement_theta_min      4.1750
_cell_measurement_theta_max      73.4060
#
# skip _cell_oxdiff_length_a  etc
#
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.054
#
# add _exptl_crystal_description manually if not present
#
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
#
# skip _exptl_crystal_face_index_h etc
#
_exptl_absorpt_correction_T_min  0.85183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#
# skip _oxdiff_exptl_absorpt_empirical_full_min   etc
#
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.2595
_diffrn_reflns_number            55300
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -79
_diffrn_reflns_limit_l_max       78
_diffrn_reflns_theta_min         3.4870
_diffrn_reflns_theta_max         74.1587
_diffrn_measured_fraction_theta_max 0.9951
_diffrn_reflns_theta_full        74.3338
_diffrn_measured_fraction_theta_full 0.9915
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2224993000
_diffrn_orient_matrix_UB_12      -0.1108636000
_diffrn_orient_matrix_UB_13      -0.0004803000
_diffrn_orient_matrix_UB_21      0.0084219000
_diffrn_orient_matrix_UB_22      -0.0025460000
_diffrn_orient_matrix_UB_23      -0.0242950000
_diffrn_orient_matrix_UB_31      0.1450631000
_diffrn_orient_matrix_UB_32      -0.1699407000
_diffrn_orient_matrix_UB_33      0.0006765000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -10.50   0.75    0.75    --  -36.95 -77.00 -60.00  126
  2  ω   -104.00 -20.00   0.75    0.75    --  -36.95 -57.00  60.00  112
  3  ω     23.00  89.00   0.75    0.75    --   36.95-125.00 -90.00   88
  4  ω     23.00  89.00   0.75    0.75    --   36.95-125.00  30.00   88
  5  ω     18.00 105.00   0.75    0.75    --   36.95  38.00 -60.00  116
  6  ω    -31.00  63.50   0.75    0.75    --   36.95 -77.00-120.00  126
  7  ω     20.00 104.00   0.75    0.75    --   36.95  57.00  90.00  112
  8  ω    -32.00 106.00   0.75    0.75    --   36.95   0.00-150.00  184
  9  ω    -30.00  54.00   0.75    0.75    --   36.95 -57.00  90.00  112
 10  ω     23.00  89.00   0.75    0.75    --   36.95-125.00 150.00   88
 11  ω     18.00 105.00   0.75    0.75    --   36.95  38.00  60.00  116
 12  ω    -30.00  54.00   0.75    0.75    --   36.95 -57.00 150.00  112
 13  ω      1.00  76.00   0.75    0.75    --   36.95 -99.00  30.00  100
 14  ω     57.00 150.00   0.75    0.99    --  111.00 178.00  30.00  124
 15  ω     91.00 178.00   0.75    0.99    --  111.00  64.00 -60.00  116
 16  ω     43.00 127.00   0.75    0.99    --  111.00 -50.00-120.00  112
 17  ω     41.00 116.00   0.75    0.99    --  111.00-111.00-150.00  100
 18  ω     43.00 127.00   0.75    0.99    --  111.00 -50.00 -60.00  112
 19  ω     42.00 145.50   0.75    0.99    --  111.00 -92.00-180.00  138
 20  ω    100.00 178.00   0.75    0.99    --  111.00 111.00  60.00  104
 21  ω     94.00 178.00   0.75    0.99    --  111.00  50.00-150.00  112
 22  ω     86.00 177.50   0.75    0.99    --  111.00  25.00 -90.00  122
 23  ω     42.00 129.00   0.75    0.99    --  111.00 -38.00   0.00  116
 24  ω     44.00 126.50   0.75    0.99    --  111.00 -55.00 164.49  110
 25  ω     65.00 177.50   0.75    0.99    --  111.00  12.00 120.00  150
 26  ω     41.00 116.00   0.75    0.99    --  111.00-111.00 -30.00  100
 27  ω     41.00 116.00   0.75    0.99    --  111.00-111.00   0.00  100
 28  ω     57.00 150.00   0.75    0.99    --  111.00 178.00-180.00  124
 29  ω     43.00 127.00   0.75    0.99    --  111.00 -50.00  30.00  112
 30  ω     43.00 137.50   0.75    0.99    --  111.00 -77.00-180.00  126
 31  ω     44.00 131.00   0.75    0.99    --  111.00 -64.00  60.00  116
 32  ω     92.00 177.50   0.75    0.99    --  111.00  38.00-180.00  114
 33  ω     92.00 177.50   0.75    0.99    --  111.00  38.00-150.00  114
 34  ω     44.00 131.00   0.75    0.99    --  111.00 -64.00 -30.00  116
 35  ω     41.00 134.00   0.75    0.99    --  111.00 -26.00 -18.19  124
 36  ω    100.00 178.00   0.75    0.99    --  111.00 111.00-120.00  104
 37  ω     91.00 178.00   0.75    0.99    --  111.00  64.00 -30.00  116
 38  ω     44.00 131.00   0.75    0.99    --  111.00 -64.00  90.00  116
 39  ω     57.00 150.00   0.75    0.99    --  111.00 178.00 -30.00  124
 40  ω     42.00 143.25   0.75    0.99    --  111.00 -92.00  30.00  135
 41  ω    117.00 151.50   0.75    0.99    --  111.00  64.00 120.00   46
 42  ω    133.00 170.50   0.75    0.99    --  111.00  25.00   0.00   50
 43  ω     53.00 102.50   0.75    0.99    --  111.00-111.00 -60.00   66
 44  ω     95.00 139.25   0.75    0.99    --  111.00  50.00 -90.00   59
 45  ω     99.00 126.00   0.75    0.99    --  111.00  25.00   0.00   36
 46  ω     41.00  90.50   0.75    0.99    --  111.00-111.00  60.00   66
 47  ω     71.00  98.00   0.75    0.99    --  111.00 -92.00  90.00   36
 48  ω     97.00 123.25   0.75    0.99    --  111.00 -92.00-120.00   35
 49  ω     96.00 174.00   0.75    0.99    --  111.00  50.00 150.00  104
 50  ω     89.00 123.50   0.75    0.99    --  111.00 -50.00 120.00   46
 51  ω     75.00 101.25   0.75    0.99    --  111.00 -64.00 -90.00   35
 52  ω    117.00 149.25   0.75    0.99    --  111.00 178.00 -90.00   43
 53  ω     41.75 116.00   0.75    0.99    --  111.00-111.00  30.00   99
 54  ω     75.00 101.25   0.75    0.99    --  111.00 -42.00-167.26   35
 55  ω     53.00  97.25   0.75    0.99    --  111.00 -32.00 162.81   59
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_space_group_IT_number           19
_space_group_crystal_system      orthorhombic
#
# skip intenisty data and ins header
# finished with crysalis pro cif file
#
#------------------------------------------------------------------------
#
# data from SHELX
#
# skip first few lines
#
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20

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'
#
# already have cell_setting and H-M space group so skip
#
loop_
_symmetry_equiv_pos_as_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'
#
# skip some lines we already have
#
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    3.913
#
# skip some more
#
_reflns_number_total             5656
_reflns_number_gt                5612
_reflns_threshold_expression     >2sigma(I)
#
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015)'
#
# add graphics and publication software to keep publcif happy
#
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_molecular_graphics    'SHELXLE (C. B. HÃ1/4bschle et al.,2011)'
#
# rest of shelx cif file 
#
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+14.1183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_number_reflns         5656
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_restrained_S_all      1.311
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6924(11) 0.1799(10) 0.62442(10) 0.0332(14) Uani 1 1 d . . .
H1 H 0.7838 0.1272 0.6351 0.040 Uiso 1 1 calc R . .
C2 C 0.7568(11) 0.1624(9) 0.60341(10) 0.0301(14) Uani 1 1 d . . .
H2 H 0.8913 0.0972 0.5999 0.036 Uiso 1 1 calc R . .
C3 C 0.6275(11) 0.2387(8) 0.58752(10) 0.0274(13) Uani 1 1 d . . .
C4 C 0.4286(11) 0.3297(9) 0.59257(11) 0.0305(14) Uani 1 1 d . . .
H4 H 0.3383 0.3805 0.5816 0.037 Uiso 1 1 calc R . .
C5 C 0.3595(11) 0.3477(8) 0.61337(11) 0.0298(14) Uani 1 1 d . . .
H5 H 0.2214 0.4093 0.6166 0.036 Uiso 1 1 calc R . .
C6 C 0.4952(9) 0.2738(7) 0.62993(11) 0.0241(13) Uani 1 1 d . . .
C7 C 0.4138(10) 0.3172(10) 0.65121(10) 0.0318(14) Uani 1 1 d . . .
H7 H 0.2641 0.3681 0.6511 0.038 Uiso 1 1 calc R . .
C9 C 0.3836(11) 0.3703(8) 0.68904(11) 0.0295(14) Uani 1 1 d . . .
H9 H 0.2383 0.4244 0.6866 0.035 Uiso 1 1 calc R . .
C8 C 0.4984(10) 0.3029(10) 0.67072(11) 0.0324(14) Uani 1 1 d . . .
C10 C 0.4538(12) 0.3674(9) 0.70923(11) 0.0320(15) Uani 1 1 d . . .
H10 H 0.5996 0.3147 0.7119 0.038 Uiso 1 1 calc R . .
C11 C 0.3307(11) 0.4363(8) 0.72756(11) 0.0290(14) Uani 1 1 d . . .
C12 C 0.1120(12) 0.5165(10) 0.72600(11) 0.0346(16) Uani 1 1 d . . .
H12 H 0.0399 0.5276 0.7126 0.042 Uiso 1 1 calc R . .
C13 C 0.0015(12) 0.5792(9) 0.74386(11) 0.0338(16) Uani 1 1 d . . .
H13 H -0.1443 0.6352 0.7425 0.041 Uiso 1 1 calc R . .
C14 C 0.1006(12) 0.5613(9) 0.76376(12) 0.0351(16) Uani 1 1 d . . .
H14 H 0.0239 0.6048 0.7759 0.042 Uiso 1 1 calc R . .
C15 C 0.3143(13) 0.4785(9) 0.76550(12) 0.0371(16) Uani 1 1 d . . .
H15 H 0.3828 0.4642 0.7790 0.045 Uiso 1 1 calc R . .
C16 C 0.4282(11) 0.4166(9) 0.74766(12) 0.0336(16) Uani 1 1 d . . .
H16 H 0.5736 0.3602 0.7491 0.040 Uiso 1 1 calc R . .
Br17 Br 0.78888(13) 0.19220(13) 0.675996(12) 0.0440(2) Uani 1 1 d . . .
O18 O 0.6829(9) 0.2319(6) 0.56644(7) 0.0352(11) Uani 1 1 d . . .
C19 C 0.8939(12) 0.1485(10) 0.56097(11) 0.0378(17) Uani 1 1 d . . .
H19A H 0.8772 0.0206 0.5625 0.057 Uiso 1 1 calc R . .
H19B H 1.0167 0.1902 0.5703 0.057 Uiso 1 1 calc R . .
H19C H 0.9333 0.1770 0.5463 0.057 Uiso 1 1 calc R . .
C21 C 0.1873(11) 0.8170(11) 0.62749(10) 0.0351(14) Uani 1 1 d . . .
H21 H 0.3016 0.8604 0.6181 0.042 Uiso 1 1 calc R . .
C22 C 0.2157(11) 0.8439(9) 0.64906(10) 0.0300(14) Uani 1 1 d . . .
H22 H 0.3447 0.9078 0.6542 0.036 Uiso 1 1 calc R . .
C23 C 0.0527(11) 0.7760(8) 0.66295(10) 0.0274(14) Uani 1 1 d . . .
C24 C -0.1391(11) 0.6940(9) 0.65529(10) 0.0311(13) Uani 1 1 d . . .
H24 H -0.2549 0.6545 0.6648 0.037 Uiso 1 1 calc R . .
C25 C -0.1671(11) 0.6676(9) 0.63378(10) 0.0320(14) Uani 1 1 d . . .
H25 H -0.2998 0.6072 0.6288 0.038 Uiso 1 1 calc R . .
C26 C -0.0027(10) 0.7287(8) 0.61924(11) 0.0260(13) Uani 1 1 d . . .
C27 C -0.0460(10) 0.6819(9) 0.59735(10) 0.0278(13) Uani 1 1 d . . .
H27 H -0.1908 0.6257 0.5954 0.033 Uiso 1 1 calc R . .
C28 C 0.0720(10) 0.7000(8) 0.57916(10) 0.0257(12) Uani 1 1 d . . .
C29 C -0.0126(11) 0.6294(8) 0.55922(11) 0.0263(14) Uani 1 1 d . . .
H29 H -0.1581 0.5720 0.5597 0.032 Uiso 1 1 calc R . .
C30 C 0.0908(10) 0.6362(8) 0.54036(10) 0.0258(13) Uani 1 1 d . . .
H30 H 0.2365 0.6934 0.5399 0.031 Uiso 1 1 calc R . .
C31 C 0.0053(12) 0.5654(9) 0.52029(11) 0.0292(14) Uani 1 1 d . . .
C32 C -0.2049(11) 0.4730(8) 0.51780(10) 0.0258(13) Uani 1 1 d . . .
H32 H -0.3011 0.4527 0.5297 0.031 Uiso 1 1 calc R . .
C33 C -0.2705(12) 0.4128(9) 0.49833(11) 0.0322(15) Uani 1 1 d . . .
H33 H -0.4100 0.3481 0.4970 0.039 Uiso 1 1 calc R . .
C34 C -0.1370(14) 0.4445(9) 0.48056(11) 0.0365(16) Uani 1 1 d . . .
H34 H -0.1856 0.4032 0.4671 0.044 Uiso 1 1 calc R . .
C35 C 0.0637(12) 0.5352(9) 0.48253(11) 0.0323(15) Uani 1 1 d . . .
H35 H 0.1534 0.5591 0.4703 0.039 Uiso 1 1 calc R . .
C36 C 0.1419(12) 0.5948(9) 0.50248(11) 0.0304(14) Uani 1 1 d . . .
H36 H 0.2855 0.6541 0.5037 0.037 Uiso 1 1 calc R . .
Br37 Br 0.35990(12) 0.82138(10) 0.577500(11) 0.03395(16) Uani 1 1 d . . .
O38 O 0.0638(8) 0.7873(7) 0.68453(7) 0.0365(12) Uani 1 1 d . . .
C39 C 0.2692(14) 0.8667(10) 0.69332(11) 0.0401(18) Uani 1 1 d . . .
H39A H 0.4054 0.8018 0.6885 0.060 Uiso 1 1 calc R . .
H39B H 0.2614 0.8626 0.7088 0.060 Uiso 1 1 calc R . .
H39C H 0.2800 0.9896 0.6887 0.060 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(9) . ?
C1 C6 1.392(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(8) . ?
C2 H2 0.9500 . ?
C3 O18 1.375(8) . ?
C3 C4 1.382(9) . ?
C4 C5 1.384(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.426(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.466(9) . ?
C7 C8 1.335(9) . ?
C7 H7 0.9500 . ?
C9 C10 1.343(9) . ?
C9 C8 1.433(9) . ?
C9 H9 0.9500 . ?
C8 Br17 1.911(7) . ?
C10 C11 1.461(9) . ?
C10 H10 0.9500 . ?
C11 C16 1.401(10) . ?
C11 C12 1.410(9) . ?
C12 C13 1.385(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O18 C19 1.420(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.392(9) . ?
C21 C26 1.392(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.364(9) . ?
C23 O38 1.372(8) . ?
C24 C25 1.387(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.454(9) . ?
C27 C28 1.347(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.458(9) . ?
C28 Br37 1.910(6) . ?
C29 C30 1.339(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.466(9) . ?
C30 H30 0.9500 . ?
C31 C36 1.397(9) . ?
C31 C32 1.415(9) . ?
C32 C33 1.369(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.358(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.417(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O38 C39 1.446(9) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C2 C1 C6 120.7(6) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
O18 C3 C4 116.0(6) . . ?
O18 C3 C2 124.4(6) . . ?
C4 C3 C2 119.5(6) . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.0(6) . . ?
C1 C6 C7 127.6(6) . . ?
C5 C6 C7 114.3(6) . . ?
C8 C7 C6 135.7(6) . . ?
C8 C7 H7 112.2 . . ?
C6 C7 H7 112.2 . . ?
C10 C9 C8 128.7(6) . . ?
C10 C9 H9 115.7 . . ?
C8 C9 H9 115.7 . . ?
C7 C8 C9 123.4(6) . . ?
C7 C8 Br17 121.4(5) . . ?
C9 C8 Br17 115.1(5) . . ?
C9 C10 C11 127.1(6) . . ?
C9 C10 H10 116.4 . . ?
C11 C10 H10 116.4 . . ?
C16 C11 C12 118.2(7) . . ?
C16 C11 C10 119.2(6) . . ?
C12 C11 C10 122.6(7) . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.0(7) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.8(7) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.7(7) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.7(7) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C3 O18 C19 117.1(5) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 122.2(6) . . ?
C22 C21 H21 118.9 . . ?
C26 C21 H21 118.9 . . ?
C21 C22 C23 119.2(6) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 O38 115.0(6) . . ?
C24 C23 C22 119.9(6) . . ?
O38 C23 C22 125.2(6) . . ?
C23 C24 C25 120.7(6) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C26 121.2(6) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 116.7(6) . . ?
C21 C26 C27 127.8(6) . . ?
C25 C26 C27 115.4(6) . . ?
C28 C27 C26 134.7(6) . . ?
C28 C27 H27 112.6 . . ?
C26 C27 H27 112.6 . . ?
C27 C28 C29 122.2(6) . . ?
C27 C28 Br37 122.7(5) . . ?
C29 C28 Br37 115.1(5) . . ?
C30 C29 C28 127.6(6) . . ?
C30 C29 H29 116.2 . . ?
C28 C29 H29 116.2 . . ?
C29 C30 C31 127.5(6) . . ?
C29 C30 H30 116.2 . . ?
C31 C30 H30 116.2 . . ?
C36 C31 C32 118.5(6) . . ?
C36 C31 C30 116.8(6) . . ?
C32 C31 C30 124.7(6) . . ?
C33 C32 C31 120.4(6) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 121.2(7) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 119.4(7) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 121.2(7) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 119.3(7) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C23 O38 C39 116.7(5) . . ?
O38 C39 H39A 109.5 . . ?
O38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_refine_diff_density_max         0.586
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_JG-E139_scale
_database_code_depnum_ccdc_archive 'CCDC 1902664'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;The Australian National University
Australia
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
_audit_creation_date             2018-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20'
_chemical_formula_sum            'C21 H20'
_chemical_formula_weight         272.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.59440(10)
_cell_length_b                   5.93120(10)
_cell_length_c                   16.3498(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.5470(10)
_cell_angle_gamma                90
_cell_volume                     806.71(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6721
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      5.2920
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 10 0.0238
0 0 -10 0.0238
-1 4 1 0.1424
1 -4 -1 0.1318
-6 0 3 0.0787
5 0 -4 0.0669

_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.048
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
0.0008 -0.0017 9.9965 0.0025 0.8426 0.4871
-0.0008 0.0017 -9.9965 -0.0025 -0.8426 -0.4871
-1.0013 3.9997 1.0027 1.0490 -0.0125 0.1182
1.0013 -3.9997 -1.0027 -1.0490 0.0125 -0.1182
-6.0016 -0.0013 3.0012 0.2911 0.5292 -0.8901
5.0012 0.0014 -4.0004 -0.2430 -0.5674 0.6687

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9802
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.744
_diffrn_reflns_theta_min         5.317
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  30.00   1.00    1.00    --  -36.95  57.00 -60.00   84
  2  ω     10.00 105.00   1.00    1.00    --   36.95  77.00 -30.00   95
  3  ω     23.00  90.00   1.00    1.00    --   36.95-125.00-120.00   67
  4  ω    -34.00  66.00   1.00    1.00    --   36.95 -19.00   0.00  100
  5  ω     20.00 104.00   1.00    1.00    --   36.95  57.00-180.00   84
  6  ω    -31.00  64.00   1.00    1.00    --   36.95 -77.00  60.00   95
  7  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00-120.00   75
  8  ω    -31.00  64.00   1.00    1.00    --   36.95 -77.00 -30.00   95
  9  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 120.00   67
 10  ω     41.00 116.00   1.00    5.00    --  111.00-111.00 120.00   75
 11  ω     42.00 130.00   1.00    5.00    --  111.00 -38.00-180.00   88
 12  ω     44.00 131.00   1.00    5.00    --  111.00 -64.00-180.00   87
 13  ω     43.00 138.00   1.00    5.00    --  111.00 -77.00  60.00   95
 14  ω     91.00 178.00   1.00    5.00    --  111.00  64.00 -90.00   87
 15  ω     41.00 116.00   1.00    5.00    --  111.00-111.00-180.00   75
 16  ω     92.00 178.00   1.00    5.00    --  111.00  38.00  90.00   86
 17  ω     42.00 178.00   1.00    5.00    --  111.00   0.00-120.00  136
 18  ω     91.00 178.00   1.00    5.00    --  111.00  64.00-120.00   87
 19  ω     94.00 175.00   1.00    5.00    --  111.00  50.00 -90.00   81
 20  ω     82.00 128.00   1.00    5.00    --  111.00 -64.00 -60.00   46
 21  ω     65.00 136.00   1.00    5.00    --  111.00 -77.00 150.00   71
 22  ω     98.00 126.00   1.00    5.00    --  111.00 -64.00  30.00   28
 23  ω     82.00 114.00   1.00    5.00    --  111.00-111.00 -90.00   32
 24  ω     46.00  76.00   1.00    5.00    --  111.00 -64.00 -60.00   30
 25  ω     41.00  70.00   1.00    5.00    --  111.00-111.00  90.00   29
 26  ω     78.00 115.00   1.00    5.00    --  111.00-111.00  90.00   37
 27  ω     42.00  99.00   1.00    5.00    --  111.00 -12.00 -30.00   57
 28  ω     86.00 116.00   1.00    5.00    --  111.00-111.00  30.00   30
 29  ω     64.00 121.00   1.00    5.00    --  111.00 -92.00 -30.00   57
 30  ω     85.00 123.00   1.00    5.00    --  111.00 -38.00 -90.00   38
 31  ω     46.00  71.00   1.00    5.00    --  111.00 -38.00 -90.00   25
 32  ω    127.00 155.00   1.00    5.00    --  111.00 -12.00 -30.00   28
 33  ω     47.00  72.00   1.00    5.00    --  111.00-111.00 150.00   25
 34  ω    101.00 157.00   1.00    5.00    --  111.00 111.00 -30.00   56
 35  ω     61.00 102.00   1.00    5.00    --  111.00 -25.00 120.00   41
 36  ω    143.00 170.00   1.00    5.00    --  111.00  50.00 120.00   27
 37  ω     67.00  93.00   1.00    5.00    --  111.00 -64.00 -30.00   26
 38  ω     74.00 100.00   1.00    5.00    --  111.00 -42.00-132.08   26
 39  ω    102.00 127.00   1.00    5.00    --  111.00 -42.00-132.08   25
 40  ω     46.00  94.00   1.00    5.00    --  111.00 -38.00  90.00   48
 41  ω     82.00 108.00   1.00    5.00    --  111.00 -92.00  90.00   26
 42  ω     41.00  68.00   1.00    5.00    --  111.00-111.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0484189000
_diffrn_orient_matrix_UB_12      0.2500651000
_diffrn_orient_matrix_UB_13      0.0002945000
_diffrn_orient_matrix_UB_21      -0.0460252000
_diffrn_orient_matrix_UB_22      -0.0357861000
_diffrn_orient_matrix_UB_23      0.0842846000
_diffrn_orient_matrix_UB_31      0.1726580000
_diffrn_orient_matrix_UB_32      0.0605602000
_diffrn_orient_matrix_UB_33      0.0487198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                3018
_reflns_number_total             3077
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.073
_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)+(0.0621P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1270
_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. Rigid bond restraints
 C1A, C3A, C1B, C3B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C1A \\sim C3A \\sim C1B \\sim C3B: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.b X=CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3B(H3BA,H3BB)
5.c Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_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
C1A C 0.441(2) 0.134(3) 0.2500(15) 0.054(7) Uani 0.52(4) 1 d . U P A 1
H1AA H 0.4645 0.0948 0.3088 0.080 Uiso 0.52(4) 1 calc GR . P A 1
H1AB H 0.5071 0.0463 0.2226 0.080 Uiso 0.52(4) 1 calc GR . P A 1
H1AC H 0.3299 0.1051 0.2240 0.080 Uiso 0.52(4) 1 calc GR . P A 1
C2 C 0.4741(3) 0.3689(5) 0.24197(17) 0.0371(6) Uani 1 1 d . . . . .
C3A C 0.590(3) 0.441(7) 0.2041(17) 0.051(6) Uani 0.52(4) 1 d . U P A 1
H3AA H 0.6503 0.3359 0.1827 0.061 Uiso 0.52(4) 1 calc R . P A 1
H3AB H 0.6092 0.5940 0.1997 0.061 Uiso 0.52(4) 1 calc R . P A 1
C4 C 0.3840(3) 0.5373(5) 0.28205(17) 0.0360(6) Uani 1 1 d . . . . .
C5 C 0.2256(3) 0.6119(5) 0.23277(16) 0.0336(5) Uani 1 1 d . . . . .
H5 H 0.1763 0.7272 0.2556 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1467(3) 0.5303(5) 0.15905(17) 0.0378(6) Uani 1 1 d . . . . .
H6 H 0.1974 0.4177 0.1357 0.045 Uiso 1 1 calc R . . . .
C7 C -0.0153(3) 0.6007(5) 0.10973(15) 0.0359(6) Uani 1 1 d . . . . .
C8 C -0.0980(3) 0.4582(5) 0.04673(17) 0.0382(6) Uani 1 1 d . . . . .
H8 H -0.0513 0.3220 0.0377 0.046 Uiso 1 1 calc R . . . .
C9 C -0.2487(3) 0.5134(6) -0.00322(18) 0.0471(7) Uani 1 1 d . . . . .
H9 H -0.3027 0.4149 -0.0450 0.057 Uiso 1 1 calc R . . . .
C10 C -0.3187(3) 0.7194(7) 0.00987(19) 0.0498(8) Uani 1 1 d . . . . .
H10 H -0.4195 0.7600 -0.0231 0.060 Uiso 1 1 calc R . . . .
C11 C -0.2346(4) 0.8614(6) 0.07307(19) 0.0459(7) Uani 1 1 d . . . . .
H11 H -0.2801 0.9980 0.0827 0.055 Uiso 1 1 calc R . . . .
C12 C -0.0850(3) 0.8032(5) 0.12177(17) 0.0409(6) Uani 1 1 d . . . . .
H12 H -0.0303 0.9018 0.1634 0.049 Uiso 1 1 calc R . . . .
C13 C 0.4479(3) 0.6136(5) 0.36085(16) 0.0367(6) Uani 1 1 d . . . . .
H13 H 0.3899 0.7226 0.3815 0.044 Uiso 1 1 calc R . . . .
C14 C 0.5966(3) 0.5425(5) 0.41552(16) 0.0326(5) Uani 1 1 d . . . . .
H14 H 0.6540 0.4295 0.3966 0.039 Uiso 1 1 calc R . . . .
C15 C 0.6588(3) 0.6301(5) 0.49346(16) 0.0366(6) Uani 1 1 d . . . . .
H15 H 0.5986 0.7421 0.5109 0.044 Uiso 1 1 calc R . . . .
C16 C 0.8098(3) 0.5683(5) 0.55311(15) 0.0354(6) Uani 1 1 d . . . . .
C17 C 0.8816(4) 0.7156(5) 0.61797(18) 0.0415(6) Uani 1 1 d . . . . .
H17 H 0.8303 0.8503 0.6241 0.050 Uiso 1 1 calc R . . . .
C18 C 1.0265(4) 0.6659(6) 0.67298(19) 0.0518(8) Uani 1 1 d . . . . .
H18 H 1.0731 0.7683 0.7151 0.062 Uiso 1 1 calc R . . . .
C19 C 1.1022(3) 0.4692(7) 0.66650(19) 0.0510(8) Uani 1 1 d . . . . .
H19 H 1.2007 0.4377 0.7038 0.061 Uiso 1 1 calc R . . . .
C20 C 1.0344(3) 0.3169(6) 0.60545(17) 0.0439(7) Uani 1 1 d . . . . .
H20 H 1.0866 0.1809 0.6026 0.053 Uiso 1 1 calc R . . . .
C21 C 0.8897(3) 0.3605(5) 0.54768(16) 0.0388(6) Uani 1 1 d . . . . .
H21 H 0.8453 0.2557 0.5060 0.047 Uiso 1 1 calc R . . . .
C1B C 0.579(2) 0.466(6) 0.1934(18) 0.039(4) Uani 0.48(4) 1 d . U P A 2
H1BA H 0.5187 0.5685 0.1521 0.058 Uiso 0.48(4) 1 calc GR . P A 2
H1BB H 0.6216 0.3471 0.1654 0.058 Uiso 0.48(4) 1 calc GR . P A 2
H1BC H 0.6659 0.5447 0.2308 0.058 Uiso 0.48(4) 1 calc GR . P A 2
C3B C 0.443(2) 0.143(4) 0.2477(16) 0.053(7) Uani 0.48(4) 1 d . U P A 2
H3BA H 0.4913 0.0386 0.2193 0.064 Uiso 0.48(4) 1 calc R . P A 2
H3BB H 0.3749 0.0948 0.2801 0.064 Uiso 0.48(4) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2 1.431(19) . ?
C2 C3A 1.37(3) . ?
C2 C4 1.510(4) . ?
C2 C1B 1.46(2) . ?
C2 C3B 1.37(2) . ?
C4 C5 1.466(4) . ?
C4 C13 1.346(4) . ?
C5 C6 1.318(4) . ?
C6 C7 1.483(4) . ?
C7 C8 1.383(4) . ?
C7 C12 1.378(4) . ?
C8 C9 1.386(4) . ?
C9 C10 1.402(5) . ?
C10 C11 1.387(5) . ?
C11 C12 1.375(4) . ?
C13 C14 1.427(4) . ?
C14 C15 1.356(4) . ?
C15 C16 1.461(4) . ?
C16 C17 1.393(4) . ?
C16 C21 1.425(4) . ?
C17 C18 1.373(4) . ?
C18 C19 1.353(5) . ?
C19 C20 1.363(5) . ?
C20 C21 1.384(4) . ?

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
C1A C2 C4 117.9(8) . . ?
C3A C2 C1A 121.8(18) . . ?
C3A C2 C4 120.2(16) . . ?
C1B C2 C4 115.5(13) . . ?
C3B C2 C4 119.2(11) . . ?
C3B C2 C1B 125.2(17) . . ?
C5 C4 C2 117.9(2) . . ?
C13 C4 C2 120.5(2) . . ?
C13 C4 C5 121.6(3) . . ?
C6 C5 C4 125.8(3) . . ?
C5 C6 C7 126.2(3) . . ?
C8 C7 C6 118.0(3) . . ?
C12 C7 C6 123.4(3) . . ?
C12 C7 C8 118.6(3) . . ?
C7 C8 C9 121.6(3) . . ?
C8 C9 C10 119.3(3) . . ?
C11 C10 C9 118.6(3) . . ?
C12 C11 C10 121.0(3) . . ?
C11 C12 C7 120.8(3) . . ?
C4 C13 C14 125.9(3) . . ?
C15 C14 C13 123.7(2) . . ?
C14 C15 C16 127.3(2) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 C21 117.5(2) . . ?
C21 C16 C15 122.5(2) . . ?
C18 C17 C16 121.3(3) . . ?
C19 C18 C17 120.6(3) . . ?
C18 C19 C20 120.2(3) . . ?
C19 C20 C21 121.4(3) . . ?
C20 C21 C16 118.9(3) . . ?


_ins_header                      
;
TITL JG-E139_scale in P2(1)/m 
REM P2(1)/m (#11 in standard setting)
CELL 1.54184   8.594375   5.931151  16.349805  90.0000 104.5472  90.0000
ZERR    2.00   0.000118   0.000074   0.000235   0.0000   0.0014   0.0000
LATT  1
SYMM -x, y+1/2,-z 
SFAC C H
UNIT 42.00 40.00
TREF
HKLF 4
END
;
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.732
