# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mw10
_database_code_depnum_ccdc_archive 'CCDC 1515156'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2016-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 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      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                   19.9896(4)
_cell_length_b                   7.31234(10)
_cell_length_c                   20.2663(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.1392(19)
_cell_angle_gamma                90
_cell_volume                     2845.58(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25466
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.6080
_cell_measurement_theta_min      4.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (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    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_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            51643
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.674
_diffrn_reflns_theta_min         4.486
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00 -30.00   99
  2  ω   -130.00  46.00   1.00    1.00    --  -41.82   0.00 150.00  176
  3  ω     23.00  98.00   1.00    1.00    --   41.82-125.00  60.00   75
  4  ω     23.00  98.00   1.00    1.00    --   41.82-125.00 -60.00   75
  5  ω     34.00 133.00   1.00    4.00    --  107.00 -45.00-180.00   99
  6  ω     33.00 131.00   1.00    4.00    --  107.00 -37.00  73.00   98
  7  ω     31.00 140.00   1.00    4.00    --  107.00 -77.00   0.00  109
  8  ω     24.00 109.00   1.00    4.00    --  107.00 -94.00  90.00   85
  9  ω     34.00 121.00   1.00    4.00    --  107.00-125.00   0.00   87
 10  ω     54.00 178.00   1.00    4.00    --  107.00  15.00  90.00  124
 11  ω     74.00 178.00   1.00    4.00    --  107.00  77.00-120.00  104
 12  ω     31.00 135.00   1.00    4.00    --  107.00 -30.00 -90.00  104
 13  ω     27.00 111.00   1.00    4.00    --  107.00-100.00-133.00   84
 14  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00 120.00  109
 15  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-180.00  100
 16  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00   0.00  100
 17  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00 -90.00  109
 18  ω     74.00 178.00   1.00    4.00    --  107.00  77.00 -90.00  104
 19  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
 20  ω     79.00 178.00   1.00    4.00    --  107.00  30.00-180.00   99
 21  ω     74.00 178.00   1.00    4.00    --  107.00  77.00  30.00  104
 22  ω     79.00 178.00   1.00    4.00    --  107.00  30.00 -30.00   99
 23  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 24  ω     74.00 178.00   1.00    4.00    --  107.00  77.00 -30.00  104
 25  ω     74.00 178.00   1.00    4.00    --  107.00  77.00  90.00  104
 26  ω    -70.00  31.00   1.00    1.00    --  -41.82  57.00-150.00  101
 27  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00  60.00  109
 28  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00-180.00  109
 29  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00   0.00  109
 30  ω     74.00 178.00   1.00    4.00    --  107.00  77.00  60.00  104
 31  ω     74.00 178.00   1.00    4.00    --  107.00  77.00 120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590079000
_diffrn_orient_matrix_UB_12      0.0348393000
_diffrn_orient_matrix_UB_13      0.0337667000
_diffrn_orient_matrix_UB_21      -0.0260237000
_diffrn_orient_matrix_UB_22      -0.1975675000
_diffrn_orient_matrix_UB_23      -0.0166970000
_diffrn_orient_matrix_UB_31      0.0477289000
_diffrn_orient_matrix_UB_32      -0.0643491000
_diffrn_orient_matrix_UB_33      0.0695839000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5302
_reflns_number_total             5691
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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         0.352
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.125
_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)+(0.0417P)²+8.7778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1841
_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 Secondary CH2 refined with riding coordinates:
 C209(H20D,H20E), C212(H21A,H21B), C109(H10D,H10E), C112(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C205(H205), C206(H206), C215(H215), C216(H216), C217(H217), C218(H218),
 C221(H221), C105(H105), C106(H106), C115(H115), C116(H116), C117(H117),
 C118(H118), C121(H121)
2.c Idealised Me refined as rotating group:
 C201(H20A,H20B,H20C), C101(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C201 C 0.59921(18) 0.8895(6) 0.54277(16) 0.0342(8) Uani 1 1 d . . . . .
H20A H 0.6200 0.7982 0.5191 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.6186 1.0104 0.5380 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.5486 0.8917 0.5224 0.051 Uiso 1 1 calc GR . . . .
O202 O 0.61458(11) 0.8427(3) 0.61476(11) 0.0256(5) Uani 1 1 d . . . . .
C203 C 0.68197(15) 0.8131(4) 0.64698(16) 0.0236(6) Uani 1 1 d . . . . .
O203 O 0.72709(12) 0.8120(4) 0.61760(12) 0.0372(6) Uani 1 1 d . . . . .
C204 C 0.69447(15) 0.7809(4) 0.72191(15) 0.0196(6) Uani 1 1 d . . . . .
C205 C 0.76106(15) 0.7360(4) 0.76132(16) 0.0216(6) Uani 1 1 d . . . . .
H205 H 0.7977 0.7214 0.7403 0.026 Uiso 1 1 calc R . . . .
C206 C 0.77372(15) 0.7124(4) 0.83150(16) 0.0214(6) Uani 1 1 d . . . . .
H206 H 0.8187 0.6770 0.8585 0.026 Uiso 1 1 calc R . . . .
C207 C 0.72085(14) 0.7405(4) 0.86245(14) 0.0178(6) Uani 1 1 d . . . . .
O208 O 0.73532(10) 0.7260(3) 0.93340(10) 0.0205(4) Uani 1 1 d . . . . .
C209 C 0.73608(14) 0.5400(4) 0.95770(15) 0.0199(6) Uani 1 1 d . . . . .
H20D H 0.7404 0.5397 1.0076 0.024 Uiso 1 1 calc R . . . .
H20E H 0.7765 0.4737 0.9501 0.024 Uiso 1 1 calc R . . . .
C210 C 0.67115(14) 0.4489(4) 0.92027(14) 0.0176(6) Uani 1 1 d . . . . .
C211 C 0.61688(15) 0.4055(4) 0.88165(15) 0.0188(6) Uani 1 1 d . . . . .
C212 C 0.54778(15) 0.3915(4) 0.83185(16) 0.0218(6) Uani 1 1 d . . . . .
H21A H 0.5475 0.2893 0.7997 0.026 Uiso 1 1 calc R . . . .
H21B H 0.5123 0.3656 0.8563 0.026 Uiso 1 1 calc R . . . .
O213 O 0.53078(10) 0.5600(3) 0.79383(10) 0.0200(4) Uani 1 1 d . . . . .
C214 C 0.53429(14) 0.7119(4) 0.83640(14) 0.0172(5) Uani 1 1 d . . . . .
C215 C 0.47650(15) 0.7544(4) 0.85916(16) 0.0238(6) Uani 1 1 d . . . . .
H215 H 0.4358 0.6810 0.8457 0.029 Uiso 1 1 calc R . . . .
C216 C 0.47877(16) 0.9045(5) 0.90154(17) 0.0277(7) Uani 1 1 d . . . . .
H216 H 0.4391 0.9366 0.9161 0.033 Uiso 1 1 calc R . . . .
C217 C 0.53936(18) 1.0076(4) 0.92257(17) 0.0282(7) Uani 1 1 d . . . . .
H217 H 0.5416 1.1080 0.9529 0.034 Uiso 1 1 calc R . . . .
C218 C 0.59673(16) 0.9645(4) 0.89940(16) 0.0229(6) Uani 1 1 d . . . . .
H218 H 0.6380 1.0357 0.9142 0.027 Uiso 1 1 calc R . . . .
C219 C 0.59455(14) 0.8178(4) 0.85468(14) 0.0163(5) Uani 1 1 d . . . . .
C220 C 0.65342(14) 0.7854(4) 0.82379(15) 0.0166(5) Uani 1 1 d . . . . .
C221 C 0.64104(14) 0.8041(4) 0.75320(15) 0.0191(6) Uani 1 1 d . . . . .
H221 H 0.5955 0.8330 0.7258 0.023 Uiso 1 1 calc R . . . .
C101 C 0.23912(19) 0.8840(6) 0.93908(17) 0.0378(8) Uani 1 1 d . . . . .
H10A H 0.2603 1.0058 0.9435 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.2751 0.7926 0.9585 0.057 Uiso 1 1 calc GR . . . .
H10C H 0.2035 0.8806 0.9639 0.057 Uiso 1 1 calc GR . . . .
O102 O 0.20745(11) 0.8439(4) 0.86731(11) 0.0321(5) Uani 1 1 d . . . . .
C103 C 0.25036(15) 0.7889(4) 0.83079(16) 0.0223(6) Uani 1 1 d . . . . .
O103 O 0.31215(12) 0.7682(4) 0.85617(13) 0.0399(6) Uani 1 1 d . . . . .
C104 C 0.21344(14) 0.7582(4) 0.75744(15) 0.0188(6) Uani 1 1 d . . . . .
C105 C 0.25305(15) 0.7157(4) 0.71258(16) 0.0220(6) Uani 1 1 d . . . . .
H105 H 0.3023 0.7075 0.7292 0.026 Uiso 1 1 calc R . . . .
C106 C 0.22019(15) 0.6855(4) 0.64392(16) 0.0208(6) Uani 1 1 d . . . . .
H106 H 0.2470 0.6546 0.6135 0.025 Uiso 1 1 calc R . . . .
C107 C 0.14821(15) 0.7000(4) 0.61904(15) 0.0180(6) Uani 1 1 d . . . . .
O108 O 0.11678(10) 0.6715(3) 0.54960(10) 0.0204(4) Uani 1 1 d . . . . .
C109 C 0.10533(15) 0.4801(4) 0.53130(15) 0.0196(6) Uani 1 1 d . . . . .
H10D H 0.1506 0.4169 0.5388 0.024 Uiso 1 1 calc R . . . .
H10E H 0.0796 0.4688 0.4821 0.024 Uiso 1 1 calc R . . . .
C110 C 0.06527(15) 0.3955(4) 0.57360(15) 0.0197(6) Uani 1 1 d . . . . .
C111 C 0.03660(15) 0.3552(4) 0.61598(15) 0.0213(6) Uani 1 1 d . . . . .
C112 C 0.00055(17) 0.3468(4) 0.66963(16) 0.0254(7) Uani 1 1 d . . . . .
H11A H -0.0495 0.3215 0.6487 0.030 Uiso 1 1 calc R . . . .
H11B H 0.0201 0.2464 0.7020 0.030 Uiso 1 1 calc R . . . .
O113 O 0.00856(11) 0.5184(3) 0.70625(10) 0.0214(4) Uani 1 1 d . . . . .
C114 C -0.01577(14) 0.6666(4) 0.66286(14) 0.0170(5) Uani 1 1 d . . . . .
C115 C -0.08663(15) 0.7070(4) 0.64487(15) 0.0233(6) Uani 1 1 d . . . . .
H115 H -0.1174 0.6347 0.6623 0.028 Uiso 1 1 calc R . . . .
C116 C -0.11216(16) 0.8529(5) 0.60156(16) 0.0279(7) Uani 1 1 d . . . . .
H116 H -0.1601 0.8841 0.5910 0.033 Uiso 1 1 calc R . . . .
C117 C -0.06790(16) 0.9530(4) 0.57375(17) 0.0273(7) Uani 1 1 d . . . . .
H117 H -0.0858 1.0491 0.5422 0.033 Uiso 1 1 calc R . . . .
C118 C 0.00297(15) 0.9125(4) 0.59216(15) 0.0209(6) Uani 1 1 d . . . . .
H118 H 0.0332 0.9822 0.5731 0.025 Uiso 1 1 calc R . . . .
C119 C 0.03046(14) 0.7714(4) 0.63799(14) 0.0167(5) Uani 1 1 d . . . . .
C120 C 0.10735(14) 0.7442(4) 0.66297(15) 0.0172(6) Uani 1 1 d . . . . .
C121 C 0.14123(14) 0.7714(4) 0.73204(15) 0.0187(6) Uani 1 1 d . . . . .
H121 H 0.1145 0.7997 0.7628 0.022 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
C201 H20A 0.9800 . ?
C201 H20B 0.9800 . ?
C201 H20C 0.9800 . ?
C201 O202 1.446(4) . ?
O202 C203 1.341(4) . ?
C203 O203 1.211(4) . ?
C203 C204 1.488(4) . ?
C204 C205 1.388(4) . ?
C204 C221 1.396(4) . ?
C205 H205 0.9500 . ?
C205 C206 1.384(4) . ?
C206 H206 0.9500 . ?
C206 C207 1.386(4) . ?
C207 O208 1.390(3) . ?
C207 C220 1.397(4) . ?
O208 C209 1.445(3) . ?
C209 H20D 0.9900 . ?
C209 H20E 0.9900 . ?
C209 C210 1.469(4) . ?
C210 C211 1.191(4) . ?
C211 C212 1.470(4) . ?
C212 H21A 0.9900 . ?
C212 H21B 0.9900 . ?
C212 O213 1.443(3) . ?
O213 C214 1.396(3) . ?
C214 C215 1.393(4) . ?
C214 C219 1.393(4) . ?
C215 H215 0.9500 . ?
C215 C216 1.386(5) . ?
C216 H216 0.9500 . ?
C216 C217 1.390(5) . ?
C217 H217 0.9500 . ?
C217 C218 1.391(4) . ?
C218 H218 0.9500 . ?
C218 C219 1.397(4) . ?
C219 C220 1.497(4) . ?
C220 C221 1.389(4) . ?
C221 H221 0.9500 . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C101 O102 1.446(4) . ?
O102 C103 1.341(4) . ?
C103 O103 1.208(4) . ?
C103 C104 1.481(4) . ?
C104 C105 1.397(4) . ?
C104 C121 1.395(4) . ?
C105 H105 0.9500 . ?
C105 C106 1.381(4) . ?
C106 H106 0.9500 . ?
C106 C107 1.390(4) . ?
C107 O108 1.388(4) . ?
C107 C120 1.403(4) . ?
O108 C109 1.450(3) . ?
C109 H10D 0.9900 . ?
C109 H10E 0.9900 . ?
C109 C110 1.463(4) . ?
C110 C111 1.194(4) . ?
C111 C112 1.463(4) . ?
C112 H11A 0.9900 . ?
C112 H11B 0.9900 . ?
C112 O113 1.444(4) . ?
O113 C114 1.395(3) . ?
C114 C115 1.393(4) . ?
C114 C119 1.398(4) . ?
C115 H115 0.9500 . ?
C115 C116 1.385(5) . ?
C116 H116 0.9500 . ?
C116 C117 1.384(5) . ?
C117 H117 0.9500 . ?
C117 C118 1.393(4) . ?
C118 H118 0.9500 . ?
C118 C119 1.395(4) . ?
C119 C120 1.492(4) . ?
C120 C121 1.390(4) . ?
C121 H121 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
H20A C201 H20B 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
O202 C201 H20A 109.5 . . ?
O202 C201 H20B 109.5 . . ?
O202 C201 H20C 109.5 . . ?
C203 O202 C201 115.6(2) . . ?
O202 C203 C204 112.5(2) . . ?
O203 C203 O202 123.1(3) . . ?
O203 C203 C204 124.3(3) . . ?
C205 C204 C203 119.1(3) . . ?
C205 C204 C221 120.0(3) . . ?
C221 C204 C203 120.8(3) . . ?
C204 C205 H205 120.2 . . ?
C206 C205 C204 119.5(3) . . ?
C206 C205 H205 120.2 . . ?
C205 C206 H206 119.9 . . ?
C205 C206 C207 120.1(3) . . ?
C207 C206 H206 119.9 . . ?
C206 C207 O208 119.4(2) . . ?
C206 C207 C220 121.3(3) . . ?
O208 C207 C220 119.3(2) . . ?
C207 O208 C209 113.8(2) . . ?
O208 C209 H20D 109.9 . . ?
O208 C209 H20E 109.9 . . ?
O208 C209 C210 109.1(2) . . ?
H20D C209 H20E 108.3 . . ?
C210 C209 H20D 109.9 . . ?
C210 C209 H20E 109.9 . . ?
C211 C210 C209 166.7(3) . . ?
C210 C211 C212 168.6(3) . . ?
C211 C212 H21A 109.6 . . ?
C211 C212 H21B 109.6 . . ?
H21A C212 H21B 108.2 . . ?
O213 C212 C211 110.1(2) . . ?
O213 C212 H21A 109.6 . . ?
O213 C212 H21B 109.6 . . ?
C214 O213 C212 112.7(2) . . ?
C215 C214 O213 118.6(3) . . ?
C219 C214 O213 119.9(2) . . ?
C219 C214 C215 121.5(3) . . ?
C214 C215 H215 120.2 . . ?
C216 C215 C214 119.6(3) . . ?
C216 C215 H215 120.2 . . ?
C215 C216 H216 120.2 . . ?
C215 C216 C217 119.7(3) . . ?
C217 C216 H216 120.2 . . ?
C216 C217 H217 119.9 . . ?
C216 C217 C218 120.2(3) . . ?
C218 C217 H217 119.9 . . ?
C217 C218 H218 119.6 . . ?
C217 C218 C219 120.9(3) . . ?
C219 C218 H218 119.6 . . ?
C214 C219 C218 117.9(3) . . ?
C214 C219 C220 121.5(3) . . ?
C218 C219 C220 120.4(3) . . ?
C207 C220 C219 123.4(3) . . ?
C221 C220 C207 117.9(3) . . ?
C221 C220 C219 118.6(2) . . ?
C204 C221 H221 119.5 . . ?
C220 C221 C204 121.1(3) . . ?
C220 C221 H221 119.5 . . ?
H10A C101 H10B 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O102 C101 H10A 109.5 . . ?
O102 C101 H10B 109.5 . . ?
O102 C101 H10C 109.5 . . ?
C103 O102 C101 116.6(2) . . ?
O102 C103 C104 112.5(2) . . ?
O103 C103 O102 122.5(3) . . ?
O103 C103 C104 125.0(3) . . ?
C105 C104 C103 118.2(3) . . ?
C121 C104 C103 122.4(3) . . ?
C121 C104 C105 119.4(3) . . ?
C104 C105 H105 120.2 . . ?
C106 C105 C104 119.6(3) . . ?
C106 C105 H105 120.2 . . ?
C105 C106 H106 119.7 . . ?
C105 C106 C107 120.5(3) . . ?
C107 C106 H106 119.7 . . ?
C106 C107 C120 120.9(3) . . ?
O108 C107 C106 119.2(3) . . ?
O108 C107 C120 119.9(2) . . ?
C107 O108 C109 113.5(2) . . ?
O108 C109 H10D 109.8 . . ?
O108 C109 H10E 109.8 . . ?
O108 C109 C110 109.4(2) . . ?
H10D C109 H10E 108.2 . . ?
C110 C109 H10D 109.8 . . ?
C110 C109 H10E 109.8 . . ?
C111 C110 C109 167.4(3) . . ?
C110 C111 C112 168.1(3) . . ?
C111 C112 H11A 109.7 . . ?
C111 C112 H11B 109.7 . . ?
H11A C112 H11B 108.2 . . ?
O113 C112 C111 109.8(2) . . ?
O113 C112 H11A 109.7 . . ?
O113 C112 H11B 109.7 . . ?
C114 O113 C112 112.4(2) . . ?
O113 C114 C119 120.2(2) . . ?
C115 C114 O113 118.7(3) . . ?
C115 C114 C119 121.0(3) . . ?
C114 C115 H115 120.1 . . ?
C116 C115 C114 119.9(3) . . ?
C116 C115 H115 120.1 . . ?
C115 C116 H116 120.0 . . ?
C117 C116 C115 120.1(3) . . ?
C117 C116 H116 120.0 . . ?
C116 C117 H117 120.1 . . ?
C116 C117 C118 119.7(3) . . ?
C118 C117 H117 120.1 . . ?
C117 C118 H118 119.4 . . ?
C117 C118 C119 121.3(3) . . ?
C119 C118 H118 119.4 . . ?
C114 C119 C120 121.8(3) . . ?
C118 C119 C114 117.9(3) . . ?
C118 C119 C120 120.2(3) . . ?
C107 C120 C119 122.8(3) . . ?
C121 C120 C107 117.7(2) . . ?
C121 C120 C119 119.4(2) . . ?
C104 C121 H121 119.1 . . ?
C120 C121 C104 121.8(3) . . ?
C120 C121 H121 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C201 O202 C203 O203 -5.2(5) . . . . ?
C201 O202 C203 C204 175.2(3) . . . . ?
O202 C203 C204 C205 175.6(3) . . . . ?
O202 C203 C204 C221 -7.5(4) . . . . ?
C203 C204 C205 C206 177.6(3) . . . . ?
C203 C204 C221 C220 -175.9(3) . . . . ?
O203 C203 C204 C205 -3.9(5) . . . . ?
O203 C203 C204 C221 173.0(3) . . . . ?
C204 C205 C206 C207 -2.5(4) . . . . ?
C205 C204 C221 C220 0.9(4) . . . . ?
C205 C206 C207 O208 -176.5(3) . . . . ?
C205 C206 C207 C220 2.6(4) . . . . ?
C206 C207 O208 C209 -81.3(3) . . . . ?
C206 C207 C220 C219 -179.8(3) . . . . ?
C206 C207 C220 C221 -1.0(4) . . . . ?
C207 O208 C209 C210 -52.0(3) . . . . ?
C207 C220 C221 C204 -0.8(4) . . . . ?
O208 C207 C220 C219 -0.6(4) . . . . ?
O208 C207 C220 C221 178.2(2) . . . . ?
O208 C209 C210 C211 11.4(14) . . . . ?
C209 C210 C211 C212 -26(3) . . . . ?
C210 C211 C212 O213 18.2(17) . . . . ?
C211 C212 O213 C214 -55.7(3) . . . . ?
C212 O213 C214 C215 -84.6(3) . . . . ?
C212 O213 C214 C219 96.0(3) . . . . ?
O213 C214 C215 C216 179.9(3) . . . . ?
O213 C214 C219 C218 -177.7(2) . . . . ?
O213 C214 C219 C220 6.7(4) . . . . ?
C214 C215 C216 C217 -1.9(5) . . . . ?
C214 C219 C220 C207 -120.3(3) . . . . ?
C214 C219 C220 C221 61.0(4) . . . . ?
C215 C214 C219 C218 2.9(4) . . . . ?
C215 C214 C219 C220 -172.8(3) . . . . ?
C215 C216 C217 C218 2.2(5) . . . . ?
C216 C217 C218 C219 0.2(5) . . . . ?
C217 C218 C219 C214 -2.6(4) . . . . ?
C217 C218 C219 C220 173.0(3) . . . . ?
C218 C219 C220 C207 64.2(4) . . . . ?
C218 C219 C220 C221 -114.6(3) . . . . ?
C219 C214 C215 C216 -0.6(4) . . . . ?
C219 C220 C221 C204 178.0(3) . . . . ?
C220 C207 O208 C209 99.5(3) . . . . ?
C221 C204 C205 C206 0.7(4) . . . . ?
C101 O102 C103 O103 2.0(5) . . . . ?
C101 O102 C103 C104 -177.8(3) . . . . ?
O102 C103 C104 C105 174.6(3) . . . . ?
O102 C103 C104 C121 -5.0(4) . . . . ?
C103 C104 C105 C106 179.7(3) . . . . ?
C103 C104 C121 C120 179.3(3) . . . . ?
O103 C103 C104 C105 -5.2(5) . . . . ?
O103 C103 C104 C121 175.2(3) . . . . ?
C104 C105 C106 C107 1.0(4) . . . . ?
C105 C104 C121 C120 -0.3(4) . . . . ?
C105 C106 C107 O108 179.1(3) . . . . ?
C105 C106 C107 C120 -0.4(4) . . . . ?
C106 C107 O108 C109 82.7(3) . . . . ?
C106 C107 C120 C119 176.5(3) . . . . ?
C106 C107 C120 C121 -0.5(4) . . . . ?
C107 O108 C109 C110 55.0(3) . . . . ?
C107 C120 C121 C104 0.9(4) . . . . ?
O108 C107 C120 C119 -3.0(4) . . . . ?
O108 C107 C120 C121 180.0(2) . . . . ?
O108 C109 C110 C111 -17.9(15) . . . . ?
C109 C110 C111 C112 30(3) . . . . ?
C110 C111 C112 O113 -19.4(17) . . . . ?
C111 C112 O113 C114 57.1(3) . . . . ?
C112 O113 C114 C115 83.4(3) . . . . ?
C112 O113 C114 C119 -96.4(3) . . . . ?
O113 C114 C115 C116 -179.7(3) . . . . ?
O113 C114 C119 C118 177.0(2) . . . . ?
O113 C114 C119 C120 -7.4(4) . . . . ?
C114 C115 C116 C117 2.9(5) . . . . ?
C114 C119 C120 C107 121.8(3) . . . . ?
C114 C119 C120 C121 -61.2(4) . . . . ?
C115 C114 C119 C118 -2.9(4) . . . . ?
C115 C114 C119 C120 172.7(3) . . . . ?
C115 C116 C117 C118 -3.2(5) . . . . ?
C116 C117 C118 C119 0.4(5) . . . . ?
C117 C118 C119 C114 2.6(4) . . . . ?
C117 C118 C119 C120 -173.1(3) . . . . ?
C118 C119 C120 C107 -62.7(4) . . . . ?
C118 C119 C120 C121 114.3(3) . . . . ?
C119 C114 C115 C116 0.2(4) . . . . ?
C119 C120 C121 C104 -176.2(3) . . . . ?
C120 C107 O108 C109 -97.8(3) . . . . ?
C121 C104 C105 C106 -0.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.410
_oxdiff_exptl_absorpt_empirical_full_min 0.365
####################################################################### 
# 
# 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_mw9
_database_code_depnum_ccdc_archive 'CCDC 1515155'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2016-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O2'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.81826(15)
_cell_length_b                   9.23296(10)
_cell_length_c                   8.32936(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1216.50(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9170
_cell_measurement_theta_min      5.3140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.260
_diffrn_reflns_theta_min         5.548
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.71 -38.00   0.00   99
  2  ω     18.00  98.00   1.00    1.00    --   41.71-125.00  60.00   80
  3  ω    100.00 178.00   1.00    4.00    --  114.00 111.00 -60.00   78
  4  ω    100.00 178.00   1.00    4.00    --  114.00 111.00   0.00   78
  5  ω     85.00 178.00   1.00    4.00    --  114.00  61.00 120.00   93
  6  ω     32.00 109.00   1.00    4.00    --  114.00 -95.00 120.00   77
  7  ω     38.00 116.00   1.00    4.00    --  114.00-111.00-120.00   78
  8  ω     86.00 178.00   1.00    4.00    --  114.00  30.00-180.00   92
  9  ω   -115.00 -14.00   1.00    1.00    --  -41.71 -57.00 -90.00  101
 10  ω   -118.00  -9.00   1.00    1.00    --  -41.71 -77.00 150.00  109
 11  ω     -4.00  83.00   1.00    1.00    --   41.71 -99.00 150.00   87
 12  ω     38.00 147.00   1.00    4.00    --  114.00 -77.00 -60.00  109
 13  ω     81.00 178.00   1.00    4.00    --  114.00  77.00  60.00   97
 14  ω     86.00 178.00   1.00    4.00    --  114.00  30.00   0.00   92
 15  ω     85.00 178.00   1.00    4.00    --  114.00  61.00 -60.00   93
 16  ω     85.00 110.00   1.00    4.00    --  114.00  61.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0728392000
_diffrn_orient_matrix_UB_12      -0.1051419000
_diffrn_orient_matrix_UB_13      -0.0386359000
_diffrn_orient_matrix_UB_21      0.0491588000
_diffrn_orient_matrix_UB_22      -0.1241992000
_diffrn_orient_matrix_UB_23      0.0807608000
_diffrn_orient_matrix_UB_31      -0.0419259000
_diffrn_orient_matrix_UB_32      0.0368569000
_diffrn_orient_matrix_UB_33      0.1619084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1242
_reflns_number_total             1299
_reflns_odcompleteness_completeness 99.86
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.239
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.109
_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)+(0.0591P)²+0.2644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O7 O 0.42583(5) 0.60894(8) 0.17529(9) 0.0280(2) Uani 1 1 d . . . . .
C6 C 0.40020(7) 0.72440(11) 0.26567(13) 0.0277(3) Uani 1 1 d . . . . .
C5 C 0.31969(7) 0.72959(13) 0.33465(14) 0.0332(3) Uani 1 1 d . . . . .
H5 H 0.2818 0.6508 0.3204 0.040 Uiso 1 1 calc R . . . .
C8 C 0.39580(7) 0.46862(11) 0.22557(13) 0.0297(3) Uani 1 1 d . . . . .
H8A H 0.3433 0.4444 0.1668 0.036 Uiso 1 1 calc R . . . .
H8B H 0.3826 0.4707 0.3417 0.036 Uiso 1 1 calc R . . . .
C1 C 0.45641(7) 0.84092(11) 0.28390(12) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.46216(7) 0.35454(11) 0.19281(13) 0.0308(3) Uani 1 1 d . . . . .
H9A H 0.4834 0.3681 0.0820 0.037 Uiso 1 1 calc R . . . .
H9B H 0.4348 0.2582 0.1978 0.037 Uiso 1 1 calc R . . . .
C2 C 0.42764(8) 0.96238(12) 0.36820(15) 0.0356(3) Uani 1 1 d . . . . .
H2 H 0.4634 1.0447 0.3765 0.043 Uiso 1 1 calc R . . . .
C4 C 0.29483(8) 0.84917(14) 0.42382(15) 0.0400(3) Uani 1 1 d . . . . .
H4 H 0.2408 0.8505 0.4737 0.048 Uiso 1 1 calc R . . . .
C3 C 0.34851(8) 0.96645(14) 0.44013(15) 0.0414(3) Uani 1 1 d . . . . .
H3 H 0.3314 1.0490 0.5000 0.050 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
O7 C6 1.3666(13) . ?
O7 C8 1.4420(12) . ?
C6 C5 1.3980(16) . ?
C6 C1 1.4039(15) . ?
C5 H5 0.9500 . ?
C5 C4 1.3875(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5119(15) . ?
C1 C1 1.490(2) 3_655 ?
C1 C2 1.3992(15) . ?
C9 C9 1.530(2) 3_655 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3882(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(2) . ?
C3 H3 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
C6 O7 C8 116.31(8) . . ?
O7 C6 C5 121.56(10) . . ?
O7 C6 C1 118.00(10) . . ?
C5 C6 C1 120.41(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.36(11) . . ?
C4 C5 H5 119.8 . . ?
O7 C8 H8A 109.6 . . ?
O7 C8 H8B 109.6 . . ?
O7 C8 C9 110.17(8) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C6 C1 C1 123.03(8) . 3_655 ?
C2 C1 C6 117.54(10) . . ?
C2 C1 C1 119.42(8) . 3_655 ?
C8 C9 C9 115.52(9) . 3_655 ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C9 C9 H9A 108.4 3_655 . ?
C9 C9 H9B 108.4 3_655 . ?
H9A C9 H9B 107.5 . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.11(11) . . ?
C3 C2 H2 118.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.11(12) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.35(11) . . ?
C4 C3 H3 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A O7 0.99 2.59 3.5572(14) 166.0 5_665

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
O7 C6 C5 C4 -179.00(10) . . . . ?
O7 C6 C1 C1 -3.03(17) . . . 3_655 ?
O7 C6 C1 C2 176.10(9) . . . . ?
O7 C8 C9 C9 74.56(12) . . . 3_655 ?
C6 O7 C8 C9 -145.81(9) . . . . ?
C6 C5 C4 C3 2.36(17) . . . . ?
C6 C1 C2 C3 3.70(16) . . . . ?
C5 C6 C1 C1 178.79(11) . . . 3_655 ?
C5 C6 C1 C2 -2.07(15) . . . . ?
C5 C4 C3 C2 -0.79(18) . . . . ?
C8 O7 C6 C5 -35.67(13) . . . . ?
C8 O7 C6 C1 146.18(9) . . . . ?
C1 C6 C5 C4 -0.89(16) . . . . ?
C1 C1 C2 C3 -177.12(11) 3_655 . . . ?
C1 C2 C3 C4 -2.31(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.833
####################################################################### 
# 
# 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_adg9
_database_code_depnum_ccdc_archive 'CCDC 1515154'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2016-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O4'
_chemical_formula_sum            'C17 H12 O4'
_chemical_formula_weight         280.27
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   23.6448(5)
_cell_length_b                   7.08950(10)
_cell_length_c                   18.3229(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.266(2)
_cell_angle_gamma                90
_cell_volume                     2679.42(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4773
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.6670
_cell_measurement_theta_min      4.2070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7620
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.865
_diffrn_reflns_theta_min         4.287
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_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  32.00   1.00    8.50    --  -41.46  38.00-150.00   88
  2  ω    -70.00  32.00   1.00    8.50    --  -41.46  57.00 -60.00  102
  3  ω   -113.00 -12.00   1.00    8.50    --  -41.46 -69.00  67.00  101
  4  ω     27.00  83.00   1.00    8.50    --   41.46  38.00 -30.00   56
  5  ω     91.00 176.00   1.00   34.00    --  114.00  45.00-120.00   85
  6  ω     90.00 160.00   1.00   34.00    --  114.00  30.00 -60.00   70
  7  ω     37.00 100.00   1.00   34.00    --  114.00 -95.00  90.00   63
  8  ω    146.00 174.00   1.00   34.00    --  114.00  61.00 -60.00   28
  9  ω     85.00 114.00   1.00   34.00    --  114.00  61.00 -60.00   29
 10  ω     86.00 161.00   1.00   34.00    --  114.00  61.00-180.00   75
 11  ω     86.00 167.00   1.00   34.00    --  114.00  61.00 150.00   81
 12  ω     43.00 138.00   1.00   34.00    --  114.00 -30.00-150.00   95
 13  ω     76.00 176.00   1.00   34.00    --  114.00  15.00 120.00  100
 14  ω     67.00  92.00   1.00   34.00    --  114.00  15.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0690161000
_diffrn_orient_matrix_UB_12      0.1177154000
_diffrn_orient_matrix_UB_13      -0.0040696000
_diffrn_orient_matrix_UB_21      0.0051349000
_diffrn_orient_matrix_UB_22      -0.1217192000
_diffrn_orient_matrix_UB_23      -0.0573319000
_diffrn_orient_matrix_UB_31      -0.0550996000
_diffrn_orient_matrix_UB_32      0.1360948000
_diffrn_orient_matrix_UB_33      -0.0477281000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2538
_reflns_number_total             2804
_reflns_odcompleteness_completeness 98.82
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.312
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.054
_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)+(0.0634P)²+0.9878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1072
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O 0.54241(5) -0.01387(12) 0.43938(6) 0.0347(2) Uani 1 1 d . . . . .
H1 H 0.5161(9) -0.076(3) 0.4531(12) 0.052 Uiso 1 1 d R . . . .
C2 C 0.55588(6) 0.15148(16) 0.47638(7) 0.0266(2) Uani 1 1 d . . . . .
O2 O 0.53513(5) 0.20447(13) 0.52260(6) 0.0348(2) Uani 1 1 d . . . . .
C3 C 0.59850(5) 0.27193(16) 0.45794(7) 0.0244(2) Uani 1 1 d . . . . .
C4 C 0.62492(5) 0.43484(17) 0.50541(7) 0.0276(2) Uani 1 1 d . . . . .
H4 H 0.6167 0.4651 0.5498 0.033 Uiso 1 1 calc R . . . .
C5 C 0.66325(5) 0.55202(17) 0.48727(7) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.6812 0.6636 0.5190 0.034 Uiso 1 1 calc R . . . .
C6 C 0.67550(5) 0.50598(15) 0.42241(7) 0.0245(2) Uani 1 1 d . . . . .
O7 O 0.71426(4) 0.62396(11) 0.40540(5) 0.0279(2) Uani 1 1 d . . . . .
C8 C 0.68099(6) 0.79474(16) 0.36206(8) 0.0321(3) Uani 1 1 d . . . . .
H8A H 0.7096 0.8712 0.3484 0.039 Uiso 1 1 calc R . . . .
H8B H 0.6697 0.8710 0.3984 0.039 Uiso 1 1 calc R . . . .
C9 C 0.62207(6) 0.74337(17) 0.28516(8) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.57769(6) 0.66144(18) 0.23034(8) 0.0322(3) Uani 1 1 d . . . . .
C11 C 0.53094(6) 0.52728(19) 0.17027(8) 0.0333(3) Uani 1 1 d . . . . .
H11A H 0.4870 0.5564 0.1610 0.040 Uiso 1 1 calc R . . . .
H11B H 0.5303 0.5386 0.1160 0.040 Uiso 1 1 calc R . . . .
O12 O 0.54857(4) 0.33710(12) 0.20178(5) 0.0295(2) Uani 1 1 d . . . . .
C13 C 0.61090(6) 0.28556(16) 0.22086(7) 0.0266(2) Uani 1 1 d . . . . .
C14 C 0.62251(7) 0.22153(18) 0.15770(8) 0.0334(3) Uani 1 1 d . . . . .
H14 H 0.5881 0.2172 0.1016 0.040 Uiso 1 1 calc R . . . .
C15 C 0.68416(7) 0.16393(18) 0.17624(9) 0.0367(3) Uani 1 1 d . . . . .
H15 H 0.6916 0.1169 0.1332 0.044 Uiso 1 1 calc R . . . .
C16 C 0.73486(7) 0.17506(17) 0.25773(9) 0.0342(3) Uani 1 1 d . . . . .
H16 H 0.7773 0.1383 0.2704 0.041 Uiso 1 1 calc R . . . .
C17 C 0.72334(6) 0.23996(16) 0.32055(8) 0.0288(3) Uani 1 1 d . . . . .
H17 H 0.7584 0.2489 0.3761 0.035 Uiso 1 1 calc R . . . .
C18 C 0.66111(5) 0.29256(15) 0.30373(7) 0.0239(2) Uani 1 1 d . . . . .
C19 C 0.64885(5) 0.34459(15) 0.37346(7) 0.0231(2) Uani 1 1 d . . . . .
C20 C 0.60983(5) 0.22891(15) 0.39209(7) 0.0236(2) Uani 1 1 d . . . . .
H20 H 0.5907 0.1193 0.3594 0.028 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
O1 H1 0.89(2) . ?
O1 C2 1.3130(15) . ?
C2 O2 1.2270(15) . ?
C2 C3 1.4805(15) . ?
C3 C4 1.3962(16) . ?
C3 C20 1.3915(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3846(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3925(17) . ?
C6 O7 1.3843(13) . ?
C6 C19 1.3993(16) . ?
O7 C8 1.4508(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.4627(18) . ?
C9 C10 1.1904(19) . ?
C10 C11 1.4658(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O12 1.4457(15) . ?
O12 C13 1.3869(14) . ?
C13 C14 1.3898(17) . ?
C13 C18 1.3981(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3847(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3985(16) . ?
C18 C19 1.4882(16) . ?
C19 C20 1.3960(15) . ?
C20 H20 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 O1 H1 108.9(13) . . ?
O1 C2 C3 114.68(10) . . ?
O2 C2 O1 123.49(11) . . ?
O2 C2 C3 121.83(11) . . ?
C4 C3 C2 118.82(10) . . ?
C20 C3 C2 120.82(10) . . ?
C20 C3 C4 120.29(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.52(11) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.87(11) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C19 121.49(10) . . ?
O7 C6 C5 119.17(10) . . ?
O7 C6 C19 119.34(10) . . ?
C6 O7 C8 112.70(9) . . ?
O7 C8 H8A 109.9 . . ?
O7 C8 H8B 109.9 . . ?
O7 C8 C9 109.01(10) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C10 C9 C8 165.01(13) . . ?
C9 C10 C11 168.64(13) . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O12 C11 C10 109.93(10) . . ?
O12 C11 H11A 109.7 . . ?
O12 C11 H11B 109.7 . . ?
C13 O12 C11 114.20(9) . . ?
O12 C13 C14 119.62(11) . . ?
O12 C13 C18 119.86(10) . . ?
C14 C13 C18 120.49(11) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.27(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.93(12) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.74(12) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.25(12) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 118.25(11) . . ?
C13 C18 C19 121.52(10) . . ?
C17 C18 C19 120.16(10) . . ?
C6 C19 C18 122.50(10) . . ?
C20 C19 C6 117.90(10) . . ?
C20 C19 C18 119.59(10) . . ?
C3 C20 C19 120.91(10) . . ?
C3 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.89(2) 1.74(2) 2.6307(12) 178(2) 5_656

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -168.67(10) . . . . ?
O1 C2 C3 C20 14.24(16) . . . . ?
C2 C3 C4 C5 -178.02(10) . . . . ?
C2 C3 C20 C19 178.58(10) . . . . ?
O2 C2 C3 C4 11.47(17) . . . . ?
O2 C2 C3 C20 -165.63(11) . . . . ?
C3 C4 C5 C6 -0.44(17) . . . . ?
C4 C3 C20 C19 1.52(17) . . . . ?
C4 C5 C6 O7 -179.58(10) . . . . ?
C4 C5 C6 C19 1.22(17) . . . . ?
C5 C6 O7 C8 -75.63(13) . . . . ?
C5 C6 C19 C18 179.89(10) . . . . ?
C5 C6 C19 C20 -0.62(16) . . . . ?
C6 O7 C8 C9 -56.37(13) . . . . ?
C6 C19 C20 C3 -0.75(16) . . . . ?
O7 C6 C19 C18 0.69(16) . . . . ?
O7 C6 C19 C20 -179.81(9) . . . . ?
O7 C8 C9 C10 9.1(6) . . . . ?
C8 C9 C10 C11 -17.5(12) . . . . ?
C9 C10 C11 O12 14.5(8) . . . . ?
C10 C11 O12 C13 -56.25(13) . . . . ?
C11 O12 C13 C14 -83.14(13) . . . . ?
C11 O12 C13 C18 98.92(12) . . . . ?
O12 C13 C14 C15 -177.98(11) . . . . ?
O12 C13 C18 C17 -179.86(10) . . . . ?
O12 C13 C18 C19 3.31(16) . . . . ?
C13 C14 C15 C16 -1.78(19) . . . . ?
C13 C18 C19 C6 -116.55(12) . . . . ?
C13 C18 C19 C20 63.96(14) . . . . ?
C14 C13 C18 C17 2.22(17) . . . . ?
C14 C13 C18 C19 -174.61(11) . . . . ?
C14 C15 C16 C17 1.38(19) . . . . ?
C15 C16 C17 C18 0.86(18) . . . . ?
C16 C17 C18 C13 -2.63(17) . . . . ?
C16 C17 C18 C19 174.24(10) . . . . ?
C17 C18 C19 C6 66.68(14) . . . . ?
C17 C18 C19 C20 -112.81(12) . . . . ?
C18 C13 C14 C15 -0.05(19) . . . . ?
C18 C19 C20 C3 178.76(10) . . . . ?
C19 C6 O7 C8 103.58(12) . . . . ?
C20 C3 C4 C5 -0.91(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.851
####################################################################### 
# 
# 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_adg4
_database_code_depnum_ccdc_archive 'CCDC 1515152'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Br2 O2'
_chemical_formula_sum            'C16 H10 Br2 O2'
_chemical_formula_weight         394.06
_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'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.16761(6)
_cell_length_b                   7.46338(4)
_cell_length_c                   28.10737(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.6158(4)
_cell_angle_gamma                90
_cell_volume                     2888.50(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22067
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.0400
_cell_measurement_theta_min      3.1950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            27581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.157
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    3.00    --  -41.71 -38.00 -90.00   99
  2  ω   -116.00 -17.00   1.00    3.00    --  -41.71 -38.00   0.00   99
  3  ω     21.00 100.00   1.00    3.00    --   41.71-128.00 -73.00   79
  4  ω     38.00 142.00   1.00    9.00    --  114.00 -30.00  90.00  104
  5  ω     61.00 178.00   1.00    9.00    --  114.00  15.00-120.00  117
  6  ω     38.00 116.00   1.00    9.00    --  114.00-111.00 -30.00   78
  7  ω     88.00 178.00   1.00    9.00    --  114.00  45.00  90.00   90
  8  ω     38.00 147.00   1.00    9.00    --  114.00 -77.00 -30.00  109
  9  ω   -118.00  -9.00   1.00    3.00    --  -41.71 -77.00-180.00  109
 10  ω      9.00 118.00   1.00    3.00    --   41.71  77.00  90.00  109
 11  ω     -4.00  83.00   1.00    3.00    --   41.71 -99.00  30.00   87
 12  ω     85.00 178.00   1.00    9.00    --  114.00  61.00  30.00   93
 13  ω     32.00 109.00   1.00    9.00    --  114.00 -95.00 150.00   77
 14  ω     81.00 178.00   1.00    9.00    --  114.00  77.00 120.00   97
 15  ω     38.00 142.00   1.00    9.00    --  114.00 -30.00 -30.00  104
 16  ω     86.00 178.00   1.00    9.00    --  114.00  30.00   0.00   92
 17  ω     86.00 178.00   1.00    9.00    --  114.00  30.00 -60.00   92
 18  ω   -114.00 -63.00   1.00    3.00    --  -41.71-142.00 115.00   51
 19  ω   -118.00  -9.00   1.00    3.00    --  -41.71 -77.00 -90.00  109
 20  ω    -70.00  31.00   1.00    3.00    --  -41.71  57.00 150.00  101
 21  ω     85.00 178.00   1.00    9.00    --  114.00  61.00 -60.00   93
 22  ω     85.00 178.00   1.00    9.00    --  114.00  61.00-120.00   93
 23  ω     81.00 178.00   1.00    9.00    --  114.00  77.00  90.00   97
 24  ω     85.00 178.00   1.00    9.00    --  114.00  61.00  60.00   93
 25  ω     85.00 178.00   1.00    9.00    --  114.00  61.00   0.00   93
 26  ω     32.00 109.00   1.00    9.00    --  114.00 -95.00-120.00   77
 27  ω     18.00  98.00   1.00    3.00    --   41.71-125.00 -30.00   80
 28  ω     14.00 115.00   1.00    3.00    --   41.71  57.00  30.00  101
 29  ω      9.00 118.00   1.00    3.00    --   41.71  77.00-180.00  109
 30  ω     38.00 116.00   1.00    9.00    --  114.00-111.00 120.00   78
 31  ω     81.00 178.00   1.00    9.00    --  114.00  77.00 150.00   97
 32  ω     42.00 143.00   1.00    9.00    --  114.00 -61.00 150.00  101
 33  ω     85.00 178.00   1.00    9.00    --  114.00  61.00 -30.00   93
 34  ω     81.00 178.00   1.00    9.00    --  114.00  77.00 -90.00   97
 35  ω     85.00 178.00   1.00    9.00    --  114.00  61.00-150.00   93
 36  ω     14.00  56.00   1.00    3.00    --   41.71  57.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0435549000
_diffrn_orient_matrix_UB_12      -0.0061635000
_diffrn_orient_matrix_UB_13      0.0453024000
_diffrn_orient_matrix_UB_21      -0.1030343000
_diffrn_orient_matrix_UB_22      0.0083571000
_diffrn_orient_matrix_UB_23      -0.0334914000
_diffrn_orient_matrix_UB_31      -0.0028302000
_diffrn_orient_matrix_UB_32      -0.2060907000
_diffrn_orient_matrix_UB_33      -0.0027177000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3051
_reflns_number_total             3075
_reflns_odcompleteness_completeness 99.94
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.083
_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)+(0.0474P)²+5.2427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0801
_refine_special_details          ?
_olex2_refinement_description    
;

There is a B alert for a short contact in the Platon cifcheck.
This is a halogen bond
O1 - Br10_$1 3.0467 (0.0015)  Angstroms

Symmetry operator used to generate symmetry equivalent atoms in 
above contact were $1 1.5-X,1.5-Y,1.5-Z

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.79913(12) 0.7796(2) 0.62172(6) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.8850(2) 0.8366(3) 0.60618(9) 0.0332(5) Uani 1 1 d . . . . .
H2A H 0.9162 0.9379 0.6267 0.040 Uiso 1 1 calc R . . . .
H2B H 0.8667 0.8775 0.5717 0.040 Uiso 1 1 calc R . . . .
C3 C 0.95292(17) 0.6864(3) 0.61084(8) 0.0289(5) Uani 1 1 d . . . . .
C4 C 0.99233(16) 0.5433(3) 0.61564(8) 0.0279(5) Uani 1 1 d . . . . .
C5 C 1.02255(15) 0.3573(3) 0.62561(9) 0.0295(5) Uani 1 1 d . . . . .
H5A H 1.0439 0.3069 0.5973 0.035 Uiso 1 1 calc R . . . .
H5B H 1.0779 0.3516 0.6546 0.035 Uiso 1 1 calc R . . . .
O6 O 0.94204(10) 0.2541(2) 0.63448(6) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.90740(14) 0.3168(3) 0.67370(8) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.95484(16) 0.2681(3) 0.72093(8) 0.0277(4) Uani 1 1 d . . . . .
H8 H 1.0115 0.1957 0.7261 0.033 Uiso 1 1 calc R . . . .
C9 C 0.91983(17) 0.3249(3) 0.76067(8) 0.0279(5) Uani 1 1 d . . . . .
H9 H 0.9513 0.2904 0.7931 0.033 Uiso 1 1 calc R . . . .
Br10 Br 0.78974(2) 0.51932(3) 0.80513(2) 0.03085(10) Uani 1 1 d . . . . .
C10 C 0.83835(15) 0.4324(3) 0.75194(7) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.79015(15) 0.4821(3) 0.70506(8) 0.0210(4) Uani 1 1 d . . . . .
H11 H 0.7343 0.5564 0.7002 0.025 Uiso 1 1 calc R . . . .
C12 C 0.82373(14) 0.4229(3) 0.66481(7) 0.0189(4) Uani 1 1 d . . . . .
C13 C 0.76573(14) 0.4625(3) 0.61434(7) 0.0192(4) Uani 1 1 d . . . . .
C14 C 0.71797(14) 0.3213(3) 0.58593(8) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.7264 0.2020 0.5980 0.026 Uiso 1 1 calc R . . . .
Br15 Br 0.59175(2) 0.16138(4) 0.50346(2) 0.03753(10) Uani 1 1 d . . . . .
C15 C 0.65835(15) 0.3555(3) 0.54021(8) 0.0231(4) Uani 1 1 d . . . . .
C16 C 0.64353(15) 0.5269(3) 0.52126(8) 0.0253(4) Uani 1 1 d . . . . .
H16 H 0.6014 0.5480 0.4901 0.030 Uiso 1 1 calc R . . . .
C17 C 0.69196(16) 0.6674(3) 0.54912(8) 0.0256(4) Uani 1 1 d . . . . .
H17 H 0.6836 0.7861 0.5367 0.031 Uiso 1 1 calc R . . . .
C18 C 0.75255(15) 0.6360(3) 0.59502(7) 0.0215(4) 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
O1 C2 1.450(3) . ?
O1 C18 1.384(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.463(4) . ?
C3 C4 1.198(4) . ?
C4 C5 1.460(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 O6 1.446(3) . ?
O6 C7 1.389(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
Br10 C10 1.901(2) . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.397(3) . ?
C13 C18 1.399(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
Br15 C15 1.896(2) . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(3) . ?

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
C18 O1 C2 113.00(16) . . ?
O1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
O1 C2 C3 109.22(18) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C4 C3 C2 166.5(2) . . ?
C3 C4 C5 167.7(2) . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O6 C5 C4 109.39(18) . . ?
O6 C5 H5A 109.8 . . ?
O6 C5 H5B 109.8 . . ?
C7 O6 C5 113.43(16) . . ?
O6 C7 C12 119.46(18) . . ?
C8 C7 O6 119.27(19) . . ?
C8 C7 C12 121.2(2) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 Br10 120.08(16) . . ?
C9 C10 C11 122.0(2) . . ?
C11 C10 Br10 117.93(16) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.00(19) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C13 122.41(18) . . ?
C11 C12 C7 118.03(18) . . ?
C11 C12 C13 119.38(18) . . ?
C14 C13 C12 118.58(19) . . ?
C14 C13 C18 118.27(19) . . ?
C18 C13 C12 123.06(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 Br15 118.76(17) . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 Br15 119.08(16) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.10(19) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
O1 C18 C13 120.22(18) . . ?
O1 C18 C17 118.94(19) . . ?
C17 C18 C13 120.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 13.8(12) . . . . ?
C2 O1 C18 C13 100.6(2) . . . . ?
C2 O1 C18 C17 -80.0(2) . . . . ?
C2 C3 C4 C5 -17(2) . . . . ?
C3 C4 C5 O6 13.8(12) . . . . ?
C4 C5 O6 C7 -59.3(2) . . . . ?
C5 O6 C7 C8 -81.8(2) . . . . ?
C5 O6 C7 C12 100.2(2) . . . . ?
O6 C7 C8 C9 -178.1(2) . . . . ?
O6 C7 C12 C11 179.27(18) . . . . ?
O6 C7 C12 C13 4.1(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C7 C12 C13 C14 65.7(3) . . . . ?
C7 C12 C13 C18 -117.9(2) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C8 C7 C12 C13 -173.9(2) . . . . ?
C8 C9 C10 Br10 -178.19(17) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
Br10 C10 C11 C12 179.40(15) . . . . ?
C10 C11 C12 C7 -1.3(3) . . . . ?
C10 C11 C12 C13 174.06(19) . . . . ?
C11 C12 C13 C14 -109.5(2) . . . . ?
C11 C12 C13 C18 67.0(3) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C12 C13 C14 C15 175.70(18) . . . . ?
C12 C13 C18 O1 4.1(3) . . . . ?
C12 C13 C18 C17 -175.20(19) . . . . ?
C13 C14 C15 Br15 -178.20(15) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C13 C18 O1 -179.44(17) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
Br15 C15 C16 C17 179.07(16) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 O1 -179.70(19) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 O1 C2 C3 -58.5(2) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.876
_oxdiff_exptl_absorpt_empirical_full_min 0.674
####################################################################### 
# 
# 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_adg
_database_code_depnum_ccdc_archive 'CCDC 1515150'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2016-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N3 O2'
_chemical_formula_sum            'C23 H19 N3 O2'
_chemical_formula_weight         369.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.54430(10)
_cell_length_b                   19.2006(2)
_cell_length_c                   20.0739(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3678.66(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10595
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.6100
_cell_measurement_theta_min      4.5770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.023
_diffrn_reflns_theta_min         4.405
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   33.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega -115.00  -14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7109 -125.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega   41.00   71.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7109 -125.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00   80.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -95.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   90.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   79.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  138.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega   61.00   87.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -95.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   59.00  147.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   98.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00  161.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -15.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
 13 omega   92.00  157.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 14 omega  -50.00   33.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 15 omega -118.00   -9.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -77.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
 16 omega -115.00  -14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  120.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0544165000
_diffrn_orient_matrix_UB_12      0.0534480000
_diffrn_orient_matrix_UB_13      0.0510604000
_diffrn_orient_matrix_UB_21      0.0239266000
_diffrn_orient_matrix_UB_22      -0.0529628000
_diffrn_orient_matrix_UB_23      0.0565137000
_diffrn_orient_matrix_UB_31      0.1500750000
_diffrn_orient_matrix_UB_32      0.0278289000
_diffrn_orient_matrix_UB_33      0.0094643000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                7153
_reflns_number_total             7685
_reflns_odcompleteness_completeness 99.93
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.268
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2943 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
The molecule have crystallised in an achiral space group
Flack x: -0.05(8) Shelx 2014
Hooft y: -0.03(8) Olex2

;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7685
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.6946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          ?
_olex2_refinement_description    
;

SIMU restraints were used to give the nitrogens and benzylic carbons of one of the 
triazines (C107 N108 N109 N110 C111 C128) similar thermal parameters to chemically 
equivalent atoms.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C227 \\sim C228 \\sim N208 \\sim N209 \\sim N210 \\sim C211 \\sim C212 \\sim
C207 \\sim C206: within 1.7A with sigma of 0.001 and sigma for terminal atoms
of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C112(H11A,H11B), C127(H12A,H12B), C207(H20A,H20B), C212(H21A,
 H21B), C227(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105), C115(H115),
 C116(H116), C117(H117), C118(H118), C121(H121), C122(H122), C123(H123),
 C124(H124), C201(H201), C202(H202), C203(H203), C204(H204), C205(H205),
 C215(H215), C216(H216), C217(H217), C218(H218), C221(H221), C222(H222),
 C223(H223), C224(H224)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C101 C 0.5227(3) 0.31545(14) 0.55331(16) 0.0458(6) Uani 1 1 d . . . . .
H101 H 0.4432 0.3055 0.5801 0.055 Uiso 1 1 calc R . . . .
C102 C 0.5437(3) 0.27909(15) 0.49430(17) 0.0536(7) Uani 1 1 d . . . . .
H102 H 0.4781 0.2446 0.4808 0.064 Uiso 1 1 calc R . . . .
C103 C 0.6587(3) 0.29278(15) 0.45543(14) 0.0493(7) Uani 1 1 d . . . . .
H103 H 0.6724 0.2679 0.4151 0.059 Uiso 1 1 calc R . . . .
C104 C 0.7542(3) 0.34253(14) 0.47486(13) 0.0417(6) Uani 1 1 d . . . . .
H104 H 0.8343 0.3516 0.4481 0.050 Uiso 1 1 calc R . . . .
C105 C 0.7336(3) 0.37950(13) 0.53357(12) 0.0357(5) Uani 1 1 d . . . . .
H105 H 0.7993 0.4141 0.5465 0.043 Uiso 1 1 calc R . . . .
C106 C 0.6178(3) 0.36638(12) 0.57333(12) 0.0338(5) Uani 1 1 d . . . . .
C107 C 0.5925(3) 0.40573(13) 0.63751(12) 0.0384(5) Uani 1 1 d . . . . .
H10A H 0.4907 0.4137 0.6431 0.046 Uiso 1 1 calc R . . . .
H10B H 0.6252 0.3772 0.6755 0.046 Uiso 1 1 calc R . . . .
N108 N 0.6654(2) 0.47259(11) 0.63816(9) 0.0340(4) Uani 1 1 d . . . . .
N109 N 0.7954(2) 0.47535(11) 0.66433(11) 0.0400(5) Uani 1 1 d . . . . .
N110 N 0.8462(2) 0.53750(11) 0.65132(10) 0.0380(5) Uani 1 1 d . . . . .
C111 C 0.7484(2) 0.57436(12) 0.61681(11) 0.0310(5) Uani 1 1 d . . . . .
C112 C 0.7713(2) 0.64625(12) 0.59215(11) 0.0316(5) Uani 1 1 d . . . . .
H11A H 0.6880 0.6754 0.6015 0.038 Uiso 1 1 calc R . . . .
H11B H 0.8533 0.6673 0.6146 0.038 Uiso 1 1 calc R . . . .
O113 O 0.79550(16) 0.64235(8) 0.52093(7) 0.0308(3) Uani 1 1 d . . . . .
C114 C 0.7414(2) 0.69738(12) 0.48518(11) 0.0285(4) Uani 1 1 d . . . . .
C115 C 0.7745(2) 0.76586(13) 0.50060(12) 0.0344(5) Uani 1 1 d . . . . .
H115 H 0.8323 0.7760 0.5379 0.041 Uiso 1 1 calc R . . . .
C116 C 0.7228(3) 0.81936(13) 0.46139(12) 0.0360(5) Uani 1 1 d . . . . .
H116 H 0.7436 0.8664 0.4724 0.043 Uiso 1 1 calc R . . . .
C117 C 0.6407(2) 0.80466(13) 0.40619(12) 0.0346(5) Uani 1 1 d . . . . .
H117 H 0.6064 0.8414 0.3791 0.041 Uiso 1 1 calc R . . . .
C118 C 0.6089(2) 0.73594(13) 0.39067(11) 0.0316(5) Uani 1 1 d . . . . .
H118 H 0.5535 0.7261 0.3525 0.038 Uiso 1 1 calc R . . . .
C119 C 0.6568(2) 0.68123(12) 0.43028(10) 0.0278(4) Uani 1 1 d . . . . .
C120 C 0.6205(2) 0.60770(12) 0.41412(10) 0.0271(4) Uani 1 1 d . . . . .
C121 C 0.6478(2) 0.58125(13) 0.35056(11) 0.0322(5) Uani 1 1 d . . . . .
H121 H 0.6895 0.6106 0.3181 0.039 Uiso 1 1 calc R . . . .
C122 C 0.6152(3) 0.51294(14) 0.33389(12) 0.0373(5) Uani 1 1 d . . . . .
H122 H 0.6339 0.4959 0.2903 0.045 Uiso 1 1 calc R . . . .
C123 C 0.5555(3) 0.46990(13) 0.38124(13) 0.0391(6) Uani 1 1 d . . . . .
H123 H 0.5352 0.4228 0.3704 0.047 Uiso 1 1 calc R . . . .
C124 C 0.5250(3) 0.49493(13) 0.44452(12) 0.0344(5) Uani 1 1 d . . . . .
H124 H 0.4831 0.4652 0.4767 0.041 Uiso 1 1 calc R . . . .
C125 C 0.5561(2) 0.56345(12) 0.46063(10) 0.0269(4) Uani 1 1 d . . . . .
O126 O 0.51577(16) 0.59436(8) 0.51953(7) 0.0283(3) Uani 1 1 d . . . . .
C127 C 0.4942(2) 0.55136(13) 0.57704(11) 0.0324(5) Uani 1 1 d . . . . .
H12A H 0.4445 0.5082 0.5639 0.039 Uiso 1 1 calc R . . . .
H12B H 0.4354 0.5764 0.6098 0.039 Uiso 1 1 calc R . . . .
C128 C 0.6321(3) 0.53314(12) 0.60803(10) 0.0311(5) Uani 1 1 d . . . . .
C201 C 0.3670(3) 0.58344(14) 0.91435(14) 0.0431(6) Uani 1 1 d . . . . .
H201 H 0.3559 0.6056 0.8724 0.052 Uiso 1 1 calc R . . . .
C202 C 0.3042(3) 0.61160(15) 0.97012(14) 0.0456(6) Uani 1 1 d . . . . .
H202 H 0.2506 0.6531 0.9665 0.055 Uiso 1 1 calc R . . . .
C203 C 0.3192(4) 0.57949(17) 1.03122(15) 0.0536(7) Uani 1 1 d . . . . .
H203 H 0.2762 0.5988 1.0697 0.064 Uiso 1 1 calc R . . . .
C204 C 0.3974(5) 0.51912(18) 1.03605(17) 0.0671(10) Uani 1 1 d . . . . .
H204 H 0.4071 0.4966 1.0779 0.081 Uiso 1 1 calc R . . . .
C205 C 0.4616(4) 0.49132(15) 0.98026(17) 0.0574(9) Uani 1 1 d . . . . .
H205 H 0.5165 0.4503 0.9841 0.069 Uiso 1 1 calc R . . . .
C206 C 0.4461(3) 0.52304(13) 0.91916(16) 0.0441(5) Uani 1 1 d . U . . .
C207 C 0.5136(3) 0.49221(14) 0.85752(16) 0.0487(5) Uani 1 1 d . U . . .
H20A H 0.5885 0.5239 0.8417 0.058 Uiso 1 1 calc R . . . .
H20B H 0.5576 0.4471 0.8692 0.058 Uiso 1 1 calc R . . . .
N208 N 0.4129(3) 0.48130(11) 0.80395(12) 0.0462(4) Uani 1 1 d . U . . .
N209 N 0.4235(3) 0.51688(12) 0.74587(13) 0.0545(5) Uani 1 1 d . U . . .
N210 N 0.3186(3) 0.49870(12) 0.70769(13) 0.0524(5) Uani 1 1 d . U . . .
C211 C 0.2395(3) 0.45164(13) 0.74106(13) 0.0431(4) Uani 1 1 d . U . . .
C212 C 0.1169(3) 0.41641(13) 0.71102(13) 0.0423(5) Uani 1 1 d . U . . .
H21A H 0.0406 0.4120 0.7442 0.051 Uiso 1 1 calc R . . . .
H21B H 0.0815 0.4435 0.6726 0.051 Uiso 1 1 calc R . . . .
O213 O 0.16264(19) 0.34829(9) 0.68949(8) 0.0382(4) Uani 1 1 d . . . . .
C214 C 0.0709(3) 0.29458(13) 0.70065(11) 0.0343(5) Uani 1 1 d . . . . .
C215 C -0.0664(3) 0.29610(16) 0.67720(12) 0.0444(6) Uani 1 1 d . . . . .
H215 H -0.1011 0.3365 0.6555 0.053 Uiso 1 1 calc R . . . .
C216 C -0.1525(3) 0.23868(16) 0.68557(14) 0.0491(7) Uani 1 1 d . . . . .
H216 H -0.2465 0.2399 0.6701 0.059 Uiso 1 1 calc R . . . .
C217 C -0.1014(3) 0.17957(15) 0.71650(13) 0.0439(6) Uani 1 1 d . . . . .
H217 H -0.1601 0.1400 0.7218 0.053 Uiso 1 1 calc R . . . .
C218 C 0.0359(3) 0.17802(13) 0.73985(12) 0.0357(5) Uani 1 1 d . . . . .
H218 H 0.0706 0.1370 0.7605 0.043 Uiso 1 1 calc R . . . .
C219 C 0.1228(3) 0.23563(13) 0.73337(10) 0.0319(5) Uani 1 1 d . . . . .
C220 C 0.2690(2) 0.23573(12) 0.75952(11) 0.0321(5) Uani 1 1 d . . . . .
C221 C 0.3654(3) 0.18592(13) 0.73904(14) 0.0421(6) Uani 1 1 d . . . . .
H221 H 0.3373 0.1507 0.7086 0.051 Uiso 1 1 calc R . . . .
C222 C 0.5022(3) 0.18689(15) 0.76248(17) 0.0517(7) Uani 1 1 d . . . . .
H222 H 0.5668 0.1523 0.7482 0.062 Uiso 1 1 calc R . . . .
C223 C 0.5445(3) 0.23745(14) 0.80613(17) 0.0490(7) Uani 1 1 d . . . . .
H223 H 0.6390 0.2387 0.8208 0.059 Uiso 1 1 calc R . . . .
C224 C 0.4497(3) 0.28695(13) 0.82908(14) 0.0392(5) Uani 1 1 d . . . . .
H224 H 0.4786 0.3215 0.8600 0.047 Uiso 1 1 calc R . . . .
C225 C 0.3121(2) 0.28534(11) 0.80628(11) 0.0297(4) Uani 1 1 d . . . . .
O226 O 0.20789(16) 0.32793(8) 0.83118(7) 0.0294(3) Uani 1 1 d . . . . .
C227 C 0.2489(3) 0.39385(12) 0.85789(12) 0.0345(4) Uani 1 1 d . U . . .
H22A H 0.3254 0.3873 0.8906 0.041 Uiso 1 1 calc R . . . .
H22B H 0.1685 0.4156 0.8811 0.041 Uiso 1 1 calc R . . . .
C228 C 0.2975(3) 0.44024(13) 0.80273(13) 0.0388(4) Uani 1 1 d . 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
C101 H101 0.9500 . ?
C101 C102 1.389(4) . ?
C101 C106 1.394(4) . ?
C102 H102 0.9500 . ?
C102 C103 1.372(5) . ?
C103 H103 0.9500 . ?
C103 C104 1.377(4) . ?
C104 H104 0.9500 . ?
C104 C105 1.390(4) . ?
C105 H105 0.9500 . ?
C105 C106 1.386(4) . ?
C106 C107 1.513(3) . ?
C107 H10A 0.9900 . ?
C107 H10B 0.9900 . ?
C107 N108 1.460(3) . ?
N108 N109 1.349(3) . ?
N108 C128 1.349(3) . ?
N109 N110 1.314(3) . ?
N110 C111 1.361(3) . ?
C111 C112 1.483(3) . ?
C111 C128 1.375(3) . ?
C112 H11A 0.9900 . ?
C112 H11B 0.9900 . ?
C112 O113 1.450(3) . ?
O113 C114 1.378(3) . ?
C114 C115 1.387(3) . ?
C114 C119 1.401(3) . ?
C115 H115 0.9500 . ?
C115 C116 1.385(4) . ?
C116 H116 0.9500 . ?
C116 C117 1.386(3) . ?
C117 H117 0.9500 . ?
C117 C118 1.389(3) . ?
C118 H118 0.9500 . ?
C118 C119 1.395(3) . ?
C119 C120 1.489(3) . ?
C120 C121 1.398(3) . ?
C120 C125 1.404(3) . ?
C121 H121 0.9500 . ?
C121 C122 1.389(4) . ?
C122 H122 0.9500 . ?
C122 C123 1.383(4) . ?
C123 H123 0.9500 . ?
C123 C124 1.389(3) . ?
C124 H124 0.9500 . ?
C124 C125 1.387(3) . ?
C125 O126 1.378(3) . ?
O126 C127 1.434(3) . ?
C127 H12A 0.9900 . ?
C127 H12B 0.9900 . ?
C127 C128 1.497(3) . ?
C201 H201 0.9500 . ?
C201 C202 1.380(4) . ?
C201 C206 1.387(4) . ?
C202 H202 0.9500 . ?
C202 C203 1.380(4) . ?
C203 H203 0.9500 . ?
C203 C204 1.382(5) . ?
C204 H204 0.9500 . ?
C204 C205 1.384(5) . ?
C205 H205 0.9500 . ?
C205 C206 1.377(4) . ?
C206 C207 1.516(4) . ?
C207 H20A 0.9900 . ?
C207 H20B 0.9900 . ?
C207 N208 1.458(4) . ?
N208 N209 1.355(3) . ?
N208 C228 1.355(3) . ?
N209 N210 1.308(4) . ?
N210 C211 1.354(3) . ?
C211 C212 1.481(4) . ?
C211 C228 1.373(4) . ?
C212 H21A 0.9900 . ?
C212 H21B 0.9900 . ?
C212 O213 1.445(3) . ?
O213 C214 1.371(3) . ?
C214 C215 1.393(4) . ?
C214 C219 1.400(3) . ?
C215 H215 0.9500 . ?
C215 C216 1.385(5) . ?
C216 H216 0.9500 . ?
C216 C217 1.382(4) . ?
C217 H217 0.9500 . ?
C217 C218 1.392(4) . ?
C218 H218 0.9500 . ?
C218 C219 1.389(4) . ?
C219 C220 1.491(3) . ?
C220 C221 1.389(3) . ?
C220 C225 1.399(3) . ?
C221 H221 0.9500 . ?
C221 C222 1.388(4) . ?
C222 H222 0.9500 . ?
C222 C223 1.368(4) . ?
C223 H223 0.9500 . ?
C223 C224 1.391(4) . ?
C224 H224 0.9500 . ?
C224 C225 1.391(3) . ?
C225 O226 1.381(3) . ?
O226 C227 1.429(3) . ?
C227 H22A 0.9900 . ?
C227 H22B 0.9900 . ?
C227 C228 1.495(3) . ?

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
C102 C101 H101 119.9 . . ?
C102 C101 C106 120.3(3) . . ?
C106 C101 H101 119.9 . . ?
C101 C102 H102 119.9 . . ?
C103 C102 C101 120.3(3) . . ?
C103 C102 H102 119.9 . . ?
C102 C103 H103 120.0 . . ?
C102 C103 C104 120.1(3) . . ?
C104 C103 H103 120.0 . . ?
C103 C104 H104 120.0 . . ?
C103 C104 C105 120.1(3) . . ?
C105 C104 H104 120.0 . . ?
C104 C105 H105 119.7 . . ?
C106 C105 C104 120.6(2) . . ?
C106 C105 H105 119.7 . . ?
C101 C106 C107 119.5(2) . . ?
C105 C106 C101 118.7(2) . . ?
C105 C106 C107 121.8(2) . . ?
C106 C107 H10A 109.3 . . ?
C106 C107 H10B 109.3 . . ?
H10A C107 H10B 107.9 . . ?
N108 C107 C106 111.7(2) . . ?
N108 C107 H10A 109.3 . . ?
N108 C107 H10B 109.3 . . ?
N109 N108 C107 118.4(2) . . ?
C128 N108 C107 129.9(2) . . ?
C128 N108 N109 111.0(2) . . ?
N110 N109 N108 107.31(19) . . ?
N109 N110 C111 108.7(2) . . ?
N110 C111 C112 123.6(2) . . ?
N110 C111 C128 108.7(2) . . ?
C128 C111 C112 127.7(2) . . ?
C111 C112 H11A 110.2 . . ?
C111 C112 H11B 110.2 . . ?
H11A C112 H11B 108.5 . . ?
O113 C112 C111 107.73(18) . . ?
O113 C112 H11A 110.2 . . ?
O113 C112 H11B 110.2 . . ?
C114 O113 C112 114.47(17) . . ?
O113 C114 C115 121.71(19) . . ?
O113 C114 C119 117.13(19) . . ?
C115 C114 C119 121.1(2) . . ?
C114 C115 H115 120.2 . . ?
C116 C115 C114 119.7(2) . . ?
C116 C115 H115 120.2 . . ?
C115 C116 H116 119.8 . . ?
C115 C116 C117 120.3(2) . . ?
C117 C116 H116 119.8 . . ?
C116 C117 H117 120.1 . . ?
C116 C117 C118 119.8(2) . . ?
C118 C117 H117 120.1 . . ?
C117 C118 H118 119.5 . . ?
C117 C118 C119 121.0(2) . . ?
C119 C118 H118 119.5 . . ?
C114 C119 C120 121.02(19) . . ?
C118 C119 C114 118.1(2) . . ?
C118 C119 C120 120.88(19) . . ?
C121 C120 C119 120.0(2) . . ?
C121 C120 C125 117.9(2) . . ?
C125 C120 C119 122.06(19) . . ?
C120 C121 H121 119.3 . . ?
C122 C121 C120 121.4(2) . . ?
C122 C121 H121 119.3 . . ?
C121 C122 H122 120.3 . . ?
C123 C122 C121 119.4(2) . . ?
C123 C122 H122 120.3 . . ?
C122 C123 H123 119.7 . . ?
C122 C123 C124 120.6(2) . . ?
C124 C123 H123 119.7 . . ?
C123 C124 H124 120.1 . . ?
C125 C124 C123 119.8(2) . . ?
C125 C124 H124 120.1 . . ?
C124 C125 C120 120.8(2) . . ?
O126 C125 C120 115.61(19) . . ?
O126 C125 C124 123.3(2) . . ?
C125 O126 C127 118.88(17) . . ?
O126 C127 H12A 109.6 . . ?
O126 C127 H12B 109.6 . . ?
O126 C127 C128 110.07(18) . . ?
H12A C127 H12B 108.2 . . ?
C128 C127 H12A 109.6 . . ?
C128 C127 H12B 109.6 . . ?
N108 C128 C111 104.4(2) . . ?
N108 C128 C127 126.5(2) . . ?
C111 C128 C127 129.0(2) . . ?
C202 C201 H201 119.8 . . ?
C202 C201 C206 120.5(3) . . ?
C206 C201 H201 119.8 . . ?
C201 C202 H202 120.0 . . ?
C203 C202 C201 120.0(3) . . ?
C203 C202 H202 120.0 . . ?
C202 C203 H203 120.2 . . ?
C202 C203 C204 119.6(3) . . ?
C204 C203 H203 120.2 . . ?
C203 C204 H204 119.8 . . ?
C203 C204 C205 120.4(3) . . ?
C205 C204 H204 119.8 . . ?
C204 C205 H205 119.9 . . ?
C206 C205 C204 120.2(3) . . ?
C206 C205 H205 119.9 . . ?
C201 C206 C207 120.1(3) . . ?
C205 C206 C201 119.3(3) . . ?
C205 C206 C207 120.6(3) . . ?
C206 C207 H20A 109.2 . . ?
C206 C207 H20B 109.2 . . ?
H20A C207 H20B 107.9 . . ?
N208 C207 C206 112.2(2) . . ?
N208 C207 H20A 109.2 . . ?
N208 C207 H20B 109.2 . . ?
N209 N208 C207 120.9(2) . . ?
C228 N208 C207 129.3(2) . . ?
C228 N208 N209 109.8(3) . . ?
N210 N209 N208 108.2(2) . . ?
N209 N210 C211 108.3(3) . . ?
N210 C211 C212 122.9(3) . . ?
N210 C211 C228 109.1(3) . . ?
C228 C211 C212 127.8(2) . . ?
C211 C212 H21A 110.3 . . ?
C211 C212 H21B 110.3 . . ?
H21A C212 H21B 108.5 . . ?
O213 C212 C211 107.2(2) . . ?
O213 C212 H21A 110.3 . . ?
O213 C212 H21B 110.3 . . ?
C214 O213 C212 116.02(18) . . ?
O213 C214 C215 122.0(2) . . ?
O213 C214 C219 117.3(2) . . ?
C215 C214 C219 120.6(3) . . ?
C214 C215 H215 120.0 . . ?
C216 C215 C214 120.0(3) . . ?
C216 C215 H215 120.0 . . ?
C215 C216 H216 120.0 . . ?
C217 C216 C215 119.9(3) . . ?
C217 C216 H216 120.0 . . ?
C216 C217 H217 120.0 . . ?
C216 C217 C218 120.0(3) . . ?
C218 C217 H217 120.0 . . ?
C217 C218 H218 119.5 . . ?
C219 C218 C217 120.9(2) . . ?
C219 C218 H218 119.5 . . ?
C214 C219 C220 119.7(2) . . ?
C218 C219 C214 118.5(2) . . ?
C218 C219 C220 121.8(2) . . ?
C221 C220 C219 121.0(2) . . ?
C221 C220 C225 118.2(2) . . ?
C225 C220 C219 120.8(2) . . ?
C220 C221 H221 119.6 . . ?
C222 C221 C220 120.9(3) . . ?
C222 C221 H221 119.6 . . ?
C221 C222 H222 119.9 . . ?
C223 C222 C221 120.2(3) . . ?
C223 C222 H222 119.9 . . ?
C222 C223 H223 119.8 . . ?
C222 C223 C224 120.4(3) . . ?
C224 C223 H223 119.8 . . ?
C223 C224 H224 120.3 . . ?
C223 C224 C225 119.3(2) . . ?
C225 C224 H224 120.3 . . ?
C224 C225 C220 120.9(2) . . ?
O226 C225 C220 115.8(2) . . ?
O226 C225 C224 123.2(2) . . ?
C225 O226 C227 117.58(18) . . ?
O226 C227 H22A 109.8 . . ?
O226 C227 H22B 109.8 . . ?
O226 C227 C228 109.56(19) . . ?
H22A C227 H22B 108.2 . . ?
C228 C227 H22A 109.8 . . ?
C228 C227 H22B 109.8 . . ?
N208 C228 C211 104.5(2) . . ?
N208 C228 C227 125.9(3) . . ?
C211 C228 C227 129.6(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
C101 C102 C103 C104 0.2(5) . . . . ?
C101 C106 C107 N108 -157.6(2) . . . . ?
C102 C101 C106 C105 -0.5(4) . . . . ?
C102 C101 C106 C107 179.6(2) . . . . ?
C102 C103 C104 C105 -0.6(4) . . . . ?
C103 C104 C105 C106 0.5(4) . . . . ?
C104 C105 C106 C101 0.0(4) . . . . ?
C104 C105 C106 C107 180.0(2) . . . . ?
C105 C106 C107 N108 22.4(3) . . . . ?
C106 C101 C102 C103 0.4(4) . . . . ?
C106 C107 N108 N109 -92.0(3) . . . . ?
C106 C107 N108 C128 77.7(3) . . . . ?
C107 N108 N109 N110 171.6(2) . . . . ?
C107 N108 C128 C111 -170.4(2) . . . . ?
C107 N108 C128 C127 13.7(4) . . . . ?
N108 N109 N110 C111 0.0(3) . . . . ?
N109 N108 C128 C111 -0.1(2) . . . . ?
N109 N108 C128 C127 -176.0(2) . . . . ?
N109 N110 C111 C112 -178.3(2) . . . . ?
N109 N110 C111 C128 -0.1(3) . . . . ?
N110 C111 C112 O113 104.4(2) . . . . ?
N110 C111 C128 N108 0.1(2) . . . . ?
N110 C111 C128 C127 175.9(2) . . . . ?
C111 C112 O113 C114 144.61(19) . . . . ?
C112 C111 C128 N108 178.3(2) . . . . ?
C112 C111 C128 C127 -6.0(4) . . . . ?
C112 O113 C114 C115 54.4(3) . . . . ?
C112 O113 C114 C119 -128.7(2) . . . . ?
O113 C114 C115 C116 177.0(2) . . . . ?
O113 C114 C119 C118 -175.68(19) . . . . ?
O113 C114 C119 C120 3.6(3) . . . . ?
C114 C115 C116 C117 -1.3(4) . . . . ?
C114 C119 C120 C121 -125.8(2) . . . . ?
C114 C119 C120 C125 55.6(3) . . . . ?
C115 C114 C119 C118 1.2(3) . . . . ?
C115 C114 C119 C120 -179.5(2) . . . . ?
C115 C116 C117 C118 0.8(4) . . . . ?
C116 C117 C118 C119 0.7(4) . . . . ?
C117 C118 C119 C114 -1.7(3) . . . . ?
C117 C118 C119 C120 179.0(2) . . . . ?
C118 C119 C120 C121 53.5(3) . . . . ?
C118 C119 C120 C125 -125.1(2) . . . . ?
C119 C114 C115 C116 0.3(3) . . . . ?
C119 C120 C121 C122 180.0(2) . . . . ?
C119 C120 C125 C124 -179.2(2) . . . . ?
C119 C120 C125 O126 6.4(3) . . . . ?
C120 C121 C122 C123 -0.5(4) . . . . ?
C120 C125 O126 C127 -159.09(18) . . . . ?
C121 C120 C125 C124 2.2(3) . . . . ?
C121 C120 C125 O126 -172.25(18) . . . . ?
C121 C122 C123 C124 1.5(4) . . . . ?
C122 C123 C124 C125 -0.7(4) . . . . ?
C123 C124 C125 C120 -1.2(3) . . . . ?
C123 C124 C125 O126 172.8(2) . . . . ?
C124 C125 O126 C127 26.6(3) . . . . ?
C125 C120 C121 C122 -1.3(3) . . . . ?
C125 O126 C127 C128 79.1(2) . . . . ?
O126 C127 C128 N108 -145.1(2) . . . . ?
O126 C127 C128 C111 40.0(3) . . . . ?
C128 N108 N109 N110 0.1(3) . . . . ?
C128 C111 C112 O113 -73.5(3) . . . . ?
C201 C202 C203 C204 0.0(5) . . . . ?
C201 C206 C207 N208 -53.2(3) . . . . ?
C202 C201 C206 C205 0.0(4) . . . . ?
C202 C201 C206 C207 179.5(3) . . . . ?
C202 C203 C204 C205 0.7(5) . . . . ?
C203 C204 C205 C206 -1.1(5) . . . . ?
C204 C205 C206 C201 0.8(5) . . . . ?
C204 C205 C206 C207 -178.8(3) . . . . ?
C205 C206 C207 N208 126.3(3) . . . . ?
C206 C201 C202 C203 -0.3(4) . . . . ?
C206 C207 N208 N209 115.6(3) . . . . ?
C206 C207 N208 C228 -61.4(3) . . . . ?
C207 N208 N209 N210 -178.3(2) . . . . ?
C207 N208 C228 C211 178.1(2) . . . . ?
C207 N208 C228 C227 -1.8(4) . . . . ?
N208 N209 N210 C211 0.3(3) . . . . ?
N209 N208 C228 C211 0.8(3) . . . . ?
N209 N208 C228 C227 -179.1(2) . . . . ?
N209 N210 C211 C212 -176.0(2) . . . . ?
N209 N210 C211 C228 0.2(3) . . . . ?
N210 C211 C212 O213 99.1(3) . . . . ?
N210 C211 C228 N208 -0.6(3) . . . . ?
N210 C211 C228 C227 179.3(2) . . . . ?
C211 C212 O213 C214 139.4(2) . . . . ?
C212 C211 C228 N208 175.3(2) . . . . ?
C212 C211 C228 C227 -4.8(4) . . . . ?
C212 O213 C214 C215 55.2(3) . . . . ?
C212 O213 C214 C219 -128.5(2) . . . . ?
O213 C214 C215 C216 175.5(2) . . . . ?
O213 C214 C219 C218 -174.15(19) . . . . ?
O213 C214 C219 C220 5.2(3) . . . . ?
C214 C215 C216 C217 -0.8(4) . . . . ?
C214 C219 C220 C221 -122.3(3) . . . . ?
C214 C219 C220 C225 58.9(3) . . . . ?
C215 C214 C219 C218 2.1(3) . . . . ?
C215 C214 C219 C220 -178.5(2) . . . . ?
C215 C216 C217 C218 0.7(4) . . . . ?
C216 C217 C218 C219 0.9(4) . . . . ?
C217 C218 C219 C214 -2.3(3) . . . . ?
C217 C218 C219 C220 178.4(2) . . . . ?
C218 C219 C220 C221 57.0(3) . . . . ?
C218 C219 C220 C225 -121.8(2) . . . . ?
C219 C214 C215 C216 -0.7(4) . . . . ?
C219 C220 C221 C222 178.8(3) . . . . ?
C219 C220 C225 C224 -177.9(2) . . . . ?
C219 C220 C225 O226 6.8(3) . . . . ?
C220 C221 C222 C223 -0.3(5) . . . . ?
C220 C225 O226 C227 -156.83(19) . . . . ?
C221 C220 C225 C224 3.3(3) . . . . ?
C221 C220 C225 O226 -172.1(2) . . . . ?
C221 C222 C223 C224 2.1(5) . . . . ?
C222 C223 C224 C225 -1.2(4) . . . . ?
C223 C224 C225 C220 -1.6(4) . . . . ?
C223 C224 C225 O226 173.4(2) . . . . ?
C224 C225 O226 C227 28.0(3) . . . . ?
C225 C220 C221 C222 -2.3(4) . . . . ?
C225 O226 C227 C228 69.4(3) . . . . ?
O226 C227 C228 N208 -135.9(2) . . . . ?
O226 C227 C228 C211 44.2(3) . . . . ?
C228 N208 N209 N210 -0.7(3) . . . . ?
C228 C211 C212 O213 -76.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_adg5
_database_code_depnum_ccdc_archive 'CCDC 1515153'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2015-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H8 Br4 O2'
_chemical_formula_sum            'C16 H8 Br4 O2'
_chemical_formula_weight         551.86
_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'
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/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                   7.84858(5)
_cell_length_b                   15.11182(7)
_cell_length_c                   13.51546(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.0480(6)
_cell_angle_gamma                90
_cell_volume                     1573.310(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16640
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      77.9180
_cell_measurement_theta_min      3.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    2.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.889
_diffrn_reflns_theta_min         4.435
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      175(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    2.50    --  -41.71  38.00-120.00   99
  2  ω   -118.00  -9.00   1.00    2.50    --  -41.71 -77.00-150.00  109
  3  ω   -122.00  -1.00   1.00    2.50    --  -41.71 -19.00  60.00  121
  4  ω     38.00 147.00   1.00   10.00    --  114.00 -77.00   0.00  109
  5  ω     85.00 178.00   1.00   10.00    --  114.00  61.00  90.00   93
  6  ω     38.00 116.00   1.00   10.00    --  114.00-111.00-180.00   78
  7  ω     41.00 140.00   1.00   10.00    --  114.00 -45.00 150.00   99
  8  ω     86.00 178.00   1.00   10.00    --  114.00  30.00 150.00   92
  9  ω     38.00 147.00   1.00   10.00    --  114.00 -77.00-180.00  109
 10  ω     38.00 116.00   1.00   10.00    --  114.00-111.00  60.00   78
 11  ω     88.00 178.00   1.00   10.00    --  114.00  45.00   0.00   90
 12  ω     38.00 116.00   1.00   10.00    --  114.00-111.00 -90.00   78
 13  ω     81.00 178.00   1.00   10.00    --  114.00  77.00-150.00   97
 14  ω     88.00 178.00   1.00   10.00    --  114.00  45.00  30.00   90
 15  ω     88.00 178.00   1.00   10.00    --  114.00  45.00 -30.00   90
 16  ω   -118.00  -9.00   1.00    2.50    --  -41.71 -77.00  60.00  109
 17  ω   -115.00 -14.00   1.00    2.50    --  -41.71 -57.00 -60.00  101
 18  ω     18.00  98.00   1.00    2.50    --   41.71-125.00  60.00   80
 19  ω    -30.00  70.00   1.00    2.50    --   41.71 -57.00  60.00  100
 20  ω     85.00 178.00   1.00   10.00    --  114.00  61.00  30.00   93
 21  ω     85.00 178.00   1.00   10.00    --  114.00  61.00  60.00   93
 22  ω     85.00 178.00   1.00   10.00    --  114.00  61.00-180.00   93
 23  ω     85.00 178.00   1.00   10.00    --  114.00  61.00 150.00   93
 24  ω     85.00 159.00   1.00   10.00    --  114.00  61.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0052641000
_diffrn_orient_matrix_UB_12      0.0910208000
_diffrn_orient_matrix_UB_13      -0.0518749000
_diffrn_orient_matrix_UB_21      -0.1528771000
_diffrn_orient_matrix_UB_22      0.0277531000
_diffrn_orient_matrix_UB_23      0.0496318000
_diffrn_orient_matrix_UB_31      0.1288542000
_diffrn_orient_matrix_UB_32      0.0365494000
_diffrn_orient_matrix_UB_33      0.0912864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3283
_reflns_number_total             3343
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.445
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.173
_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)+(0.0357P)²+0.9267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br8 Br -0.25202(3) 0.69173(2) 0.57812(2) 0.02614(8) Uani 1 1 d . . . . .
Br10 Br 0.26993(3) 0.58631(2) 0.36811(2) 0.02430(8) Uani 1 1 d . . . . .
Br15 Br 0.15510(3) 0.29024(2) 0.92142(2) 0.02087(8) Uani 1 1 d . . . . .
Br17 Br 0.79025(3) 0.46767(2) 0.92433(2) 0.02472(8) Uani 1 1 d . . . . .
O1 O 0.5611(2) 0.57606(11) 0.75723(13) 0.0178(3) Uani 1 1 d . . . . .
O6 O -0.0055(2) 0.60519(11) 0.75533(13) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.5707(3) 0.65745(15) 0.81502(19) 0.0202(4) Uani 1 1 d . . . . .
H2A H 0.6250 0.7045 0.7806 0.024 Uiso 1 1 calc R . . . .
H2B H 0.6431 0.6482 0.8827 0.024 Uiso 1 1 calc R . . . .
C3 C 0.3945(3) 0.68480(15) 0.82502(18) 0.0198(5) Uani 1 1 d . . . . .
C4 C 0.2447(4) 0.69038(16) 0.82742(19) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.0547(3) 0.68454(18) 0.8116(2) 0.0256(5) Uani 1 1 d . . . . .
H5A H 0.0176 0.6833 0.8776 0.031 Uiso 1 1 calc R . . . .
H5B H 0.0024 0.7373 0.7742 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0529(3) 0.59684(14) 0.66621(17) 0.0143(4) Uani 1 1 d . . . . .
C8 C -0.0391(3) 0.63384(14) 0.57718(18) 0.0147(4) Uani 1 1 d . . . . .
C9 C 0.0206(3) 0.62894(14) 0.48682(17) 0.0159(4) Uani 1 1 d . . . . .
H9 H -0.0440 0.6536 0.4265 0.019 Uiso 1 1 calc R . . . .
C10 C 0.1776(3) 0.58680(13) 0.48805(17) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.2695(3) 0.54577(14) 0.57307(17) 0.0147(4) Uani 1 1 d . . . . .
H11 H 0.3747 0.5155 0.5706 0.018 Uiso 1 1 calc R . . . .
C12 C 0.2057(3) 0.54926(14) 0.66328(16) 0.0140(4) Uani 1 1 d . . . . .
C13 C 0.2937(3) 0.49699(14) 0.75169(16) 0.0147(4) Uani 1 1 d . . . . .
C14 C 0.2005(3) 0.43143(14) 0.79100(17) 0.0160(4) Uani 1 1 d . . . . .
H14 H 0.0805 0.4231 0.7644 0.019 Uiso 1 1 calc R . . . .
C15 C 0.2843(3) 0.37869(14) 0.86904(17) 0.0157(4) Uani 1 1 d . . . . .
C16 C 0.4596(3) 0.38780(15) 0.90998(17) 0.0174(4) Uani 1 1 d . . . . .
H16 H 0.5154 0.3500 0.9625 0.021 Uiso 1 1 calc R . . . .
C17 C 0.5509(3) 0.45467(15) 0.87116(17) 0.0161(4) Uani 1 1 d . . . . .
C18 C 0.4702(3) 0.50991(14) 0.79351(17) 0.0152(4) 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
Br8 C8 1.889(2) . ?
Br10 C10 1.898(2) . ?
Br15 C15 1.895(2) . ?
Br17 C17 1.889(2) . ?
O1 C2 1.451(3) . ?
O1 C18 1.372(3) . ?
O6 C5 1.450(3) . ?
O6 C7 1.374(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.474(4) . ?
C3 C4 1.185(4) . ?
C4 C5 1.469(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.396(3) . ?
C7 C12 1.405(3) . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.405(3) . ?
C12 C13 1.487(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.406(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(3) . ?
C17 C18 1.395(3) . ?

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
C18 O1 C2 113.68(17) . . ?
C7 O6 C5 113.97(18) . . ?
O1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
O1 C2 C3 109.55(18) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C4 C3 C2 167.2(2) . . ?
C3 C4 C5 167.7(3) . . ?
O6 C5 C4 110.2(2) . . ?
O6 C5 H5A 109.6 . . ?
O6 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O6 C7 C8 121.0(2) . . ?
O6 C7 C12 120.1(2) . . ?
C8 C7 C12 118.9(2) . . ?
C7 C8 Br8 119.47(17) . . ?
C9 C8 Br8 118.54(16) . . ?
C9 C8 C7 122.0(2) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 Br10 118.44(17) . . ?
C11 C10 Br10 118.99(16) . . ?
C11 C10 C9 122.6(2) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C11 119.4(2) . . ?
C7 C12 C13 121.1(2) . . ?
C11 C12 C13 119.3(2) . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 C18 119.5(2) . . ?
C18 C13 C12 121.3(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 Br15 118.74(17) . . ?
C14 C15 C16 122.5(2) . . ?
C16 C15 Br15 118.79(17) . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.5(2) . . ?
C17 C16 H16 121.2 . . ?
C16 C17 Br17 118.46(17) . . ?
C18 C17 Br17 119.96(17) . . ?
C18 C17 C16 121.6(2) . . ?
O1 C18 C13 119.8(2) . . ?
O1 C18 C17 120.8(2) . . ?
C17 C18 C13 119.3(2) . . ?

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
Br8 C8 C9 C10 179.52(15) . . . . ?
Br10 C10 C11 C12 177.21(16) . . . . ?
Br15 C15 C16 C17 -178.82(16) . . . . ?
Br17 C17 C18 O1 -2.3(3) . . . . ?
Br17 C17 C18 C13 177.26(16) . . . . ?
O1 C2 C3 C4 16.0(13) . . . . ?
O6 C7 C8 Br8 -2.8(3) . . . . ?
O6 C7 C8 C9 177.7(2) . . . . ?
O6 C7 C12 C11 -176.18(19) . . . . ?
O6 C7 C12 C13 8.4(3) . . . . ?
C2 O1 C18 C13 95.7(2) . . . . ?
C2 O1 C18 C17 -84.7(3) . . . . ?
C2 C3 C4 C5 -36(2) . . . . ?
C3 C4 C5 O6 21.8(14) . . . . ?
C5 O6 C7 C8 -88.2(3) . . . . ?
C5 O6 C7 C12 92.9(2) . . . . ?
C7 O6 C5 C4 -53.7(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C7 C12 C13 C14 56.7(3) . . . . ?
C7 C12 C13 C18 -126.0(2) . . . . ?
C8 C7 C12 C11 4.9(3) . . . . ?
C8 C7 C12 C13 -170.47(19) . . . . ?
C8 C9 C10 Br10 -175.69(16) . . . . ?
C8 C9 C10 C11 3.9(3) . . . . ?
C9 C10 C11 C12 -2.4(3) . . . . ?
C10 C11 C12 C7 -2.1(3) . . . . ?
C10 C11 C12 C13 173.33(19) . . . . ?
C11 C12 C13 C14 -118.7(2) . . . . ?
C11 C12 C13 C18 58.7(3) . . . . ?
C12 C7 C8 Br8 176.13(15) . . . . ?
C12 C7 C8 C9 -3.4(3) . . . . ?
C12 C13 C14 C15 175.9(2) . . . . ?
C12 C13 C18 O1 4.7(3) . . . . ?
C12 C13 C18 C17 -174.9(2) . . . . ?
C13 C14 C15 Br15 179.87(16) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C13 C18 O1 -178.01(19) . . . . ?
C14 C13 C18 C17 2.4(3) . . . . ?
C14 C15 C16 C17 1.5(3) . . . . ?
C15 C16 C17 Br17 -179.24(16) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 O1 179.1(2) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C18 O1 C2 C3 -52.6(3) . . . . ?
C18 C13 C14 C15 -1.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.408
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_adg1
_database_code_depnum_ccdc_archive 'CCDC 1515151'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2015-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 O2'
_chemical_formula_sum            'C24 H16 O2'
_chemical_formula_weight         336.37
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O2'
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      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   13.54378(8)
_cell_length_b                   13.54378(8)
_cell_length_c                   48.3660(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7683.33(10)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    28020
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7950
_cell_measurement_theta_min      3.6410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            42875
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.962
_diffrn_reflns_theta_min         3.655
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   32.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00    3.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  125.0000 -150.0000 132

#__ type_ start__ end____ width___ exp.time_
  3 omega -111.00  -81.75   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   26.50   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109   38.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -16.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -90.0000 132

#__ type_ start__ end____ width___ exp.time_
  6 omega  -70.00  -16.00   0.7500   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7109  -57.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   82.25   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   96.50   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  146.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.50  116.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   90.50   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  167.25   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -120.0000 107

#__ type_ start__ end____ width___ exp.time_
 13 omega   94.00  178.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega  112.00  166.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 15 omega   54.50   92.00   0.7500   80.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -60.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0618576000
_diffrn_orient_matrix_UB_12      0.0213464000
_diffrn_orient_matrix_UB_13      -0.0239960000
_diffrn_orient_matrix_UB_21      0.0452656000
_diffrn_orient_matrix_UB_22      -0.0558343000
_diffrn_orient_matrix_UB_23      -0.0202768000
_diffrn_orient_matrix_UB_31      -0.1066615000
_diffrn_orient_matrix_UB_32      -0.1169032000
_diffrn_orient_matrix_UB_33      0.0053029000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                10491
_reflns_number_total             10592
_reflns_odcompleteness_completeness 99.91
_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, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 4938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         10592
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.041
_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)+(0.0636P)²+0.1283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          
;
 Refined as a 2-component twin.

Merohedral twin refined with 
TWIN 0 1 0 1 0 0 0 0 -1 2
BASF 0.667

;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.3330(14) 0.6670(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C302(H30A,H30B), C305(H30C,H30D), C202(H20A,H20B), C205(H20C,H20D), C102(H10A,
 H10B), C105(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 C308(H308), C309(H309), C311(H311), C312(H312), C313(H313), C314(H314),
 C319(H319), C320(H320), C321(H321), C322(H322), C324(H324), C325(H325),
 C208(H208), C209(H209), C211(H211), C212(H212), C213(H213), C214(H214),
 C219(H219), C220(H220), C221(H221), C222(H222), C224(H224), C225(H225),
 C108(H108), C109(H109), C111(H111), C112(H112), C113(H113), C114(H114),
 C119(H119), C120(H120), C121(H121), C122(H122), C124(H124), C125(H125)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O301 O 0.83475(15) 0.25427(15) -0.15282(3) 0.0270(4) Uani 1 1 d . . . . .
C302 C 0.8592(2) 0.1616(2) -0.15283(6) 0.0324(5) Uani 1 1 d . . . . .
H30A H 0.8479 0.1284 -0.1716 0.039 Uiso 1 1 calc R . . . .
H30B H 0.8074 0.1010 -0.1399 0.039 Uiso 1 1 calc R . . . .
C303 C 0.9782(2) 0.2083(2) -0.14410(6) 0.0320(5) Uani 1 1 d . . . . .
C304 C 1.0721(3) 0.2685(2) -0.13541(6) 0.0326(5) Uani 1 1 d . . . . .
C305 C 1.1807(2) 0.3645(3) -0.12618(6) 0.0337(6) Uani 1 1 d . . . . .
H30C H 1.2065 0.3432 -0.1092 0.040 Uiso 1 1 calc R . . . .
H30D H 1.2394 0.3843 -0.1406 0.040 Uiso 1 1 calc R . . . .
O306 O 1.16652(14) 0.46147(16) -0.12067(3) 0.0259(3) Uani 1 1 d . . . . .
C307 C 1.1341(2) 0.5006(2) -0.14379(5) 0.0242(4) Uani 1 1 d . . . . .
C308 C 1.2192(2) 0.5684(2) -0.16325(5) 0.0284(5) Uani 1 1 d . . . . .
H308 H 1.2948 0.5821 -0.1611 0.034 Uiso 1 1 calc R . . . .
C309 C 1.1924(2) 0.6141(2) -0.18516(5) 0.0302(5) Uani 1 1 d . . . . .
H309 H 1.2502 0.6611 -0.1980 0.036 Uiso 1 1 calc R . . . .
C310 C 1.0795(2) 0.5925(2) -0.18907(5) 0.0264(5) Uani 1 1 d . . . . .
C311 C 1.0496(3) 0.6385(2) -0.21187(5) 0.0354(6) Uani 1 1 d . . . . .
H311 H 1.1062 0.6848 -0.2250 0.042 Uiso 1 1 calc R . . . .
C312 C 0.9410(3) 0.6173(3) -0.21516(5) 0.0418(7) Uani 1 1 d . . . . .
H312 H 0.9222 0.6486 -0.2305 0.050 Uiso 1 1 calc R . . . .
C313 C 0.8561(3) 0.5488(3) -0.19577(5) 0.0366(6) Uani 1 1 d . . . . .
H313 H 0.7803 0.5340 -0.1982 0.044 Uiso 1 1 calc R . . . .
C314 C 0.8820(2) 0.5035(2) -0.17343(5) 0.0280(5) Uani 1 1 d . . . . .
H314 H 0.8239 0.4575 -0.1606 0.034 Uiso 1 1 calc R . . . .
C315 C 0.9942(2) 0.52433(19) -0.16931(4) 0.0219(4) Uani 1 1 d . . . . .
C316 C 1.02436(19) 0.47900(18) -0.14616(4) 0.0202(4) Uani 1 1 d . . . . .
C317 C 0.93884(19) 0.4173(2) -0.12387(4) 0.0205(4) Uani 1 1 d . . . . .
C318 C 0.9477(2) 0.4749(2) -0.09841(4) 0.0232(4) Uani 1 1 d . . . . .
C319 C 1.0354(2) 0.5881(2) -0.09351(5) 0.0272(5) Uani 1 1 d . . . . .
H319 H 1.0902 0.6284 -0.1075 0.033 Uiso 1 1 calc R . . . .
C320 C 1.0424(3) 0.6407(2) -0.06864(5) 0.0345(6) Uani 1 1 d . . . . .
H320 H 1.1011 0.7173 -0.0658 0.041 Uiso 1 1 calc R . . . .
C321 C 0.9638(3) 0.5822(3) -0.04744(6) 0.0397(6) Uani 1 1 d . . . . .
H321 H 0.9709 0.6186 -0.0302 0.048 Uiso 1 1 calc R . . . .
C322 C 0.8777(3) 0.4738(3) -0.05154(5) 0.0394(6) Uani 1 1 d . . . . .
H322 H 0.8240 0.4355 -0.0372 0.047 Uiso 1 1 calc R . . . .
C323 C 0.8666(2) 0.4168(2) -0.07700(5) 0.0297(5) Uani 1 1 d . . . . .
C324 C 0.7788(2) 0.3018(3) -0.08148(6) 0.0377(6) Uani 1 1 d . . . . .
H324 H 0.7252 0.2618 -0.0672 0.045 Uiso 1 1 calc R . . . .
C325 C 0.7709(2) 0.2490(2) -0.10596(5) 0.0338(6) Uani 1 1 d . . . . .
H325 H 0.7120 0.1724 -0.1087 0.041 Uiso 1 1 calc R . . . .
C326 C 0.8500(2) 0.3074(2) -0.12733(5) 0.0252(5) Uani 1 1 d . . . . .
O201 O 0.49190(14) 0.61490(15) -0.14626(4) 0.0273(3) Uani 1 1 d . . . . .
C202 C 0.4868(2) 0.5071(2) -0.14166(6) 0.0333(5) Uani 1 1 d . . . . .
H20A H 0.4597 0.4600 -0.1586 0.040 Uiso 1 1 calc R . . . .
H20B H 0.4324 0.4652 -0.1265 0.040 Uiso 1 1 calc R . . . .
C203 C 0.6006(2) 0.5275(2) -0.13426(6) 0.0313(5) Uani 1 1 d . . . . .
C204 C 0.6967(2) 0.5652(2) -0.12700(5) 0.0311(5) Uani 1 1 d . . . . .
C205 C 0.8161(2) 0.6435(2) -0.11986(6) 0.0316(5) Uani 1 1 d . . . . .
H20C H 0.8335 0.6244 -0.1014 0.038 Uiso 1 1 calc R . . . .
H20D H 0.8670 0.6373 -0.1336 0.038 Uiso 1 1 calc R . . . .
O206 O 0.83382(15) 0.75819(15) -0.11976(3) 0.0269(3) Uani 1 1 d . . . . .
C207 C 0.80764(19) 0.7926(2) -0.14441(5) 0.0248(4) Uani 1 1 d . . . . .
C208 C 0.8807(2) 0.8160(3) -0.16743(5) 0.0375(6) Uani 1 1 d . . . . .
H208 H 0.9418 0.8005 -0.1664 0.045 Uiso 1 1 calc R . . . .
C209 C 0.8640(2) 0.8602(3) -0.19087(5) 0.0411(7) Uani 1 1 d . . . . .
H209 H 0.9125 0.8741 -0.2063 0.049 Uiso 1 1 calc R . . . .
C210 C 0.7749(2) 0.8861(2) -0.19265(5) 0.0323(6) Uani 1 1 d . . . . .
C211 C 0.7590(3) 0.9378(3) -0.21658(5) 0.0432(7) Uani 1 1 d . . . . .
H211 H 0.8095 0.9560 -0.2318 0.052 Uiso 1 1 calc R . . . .
C212 C 0.6735(3) 0.9616(3) -0.21799(6) 0.0467(8) Uani 1 1 d . . . . .
H212 H 0.6643 0.9963 -0.2341 0.056 Uiso 1 1 calc R . . . .
C213 C 0.5974(3) 0.9348(2) -0.19546(6) 0.0407(6) Uani 1 1 d . . . . .
H213 H 0.5382 0.9529 -0.1964 0.049 Uiso 1 1 calc R . . . .
C214 C 0.6087(2) 0.8827(2) -0.17227(5) 0.0306(5) Uani 1 1 d . . . . .
H214 H 0.5556 0.8627 -0.1576 0.037 Uiso 1 1 calc R . . . .
C215 C 0.6983(2) 0.8585(2) -0.17011(4) 0.0248(5) Uani 1 1 d . . . . .
C216 C 0.71545(19) 0.80838(19) -0.14566(4) 0.0214(4) Uani 1 1 d . . . . .
C217 C 0.6343(2) 0.7797(2) -0.12205(4) 0.0207(4) Uani 1 1 d . . . . .
C218 C 0.6648(2) 0.8551(2) -0.09898(4) 0.0216(4) Uani 1 1 d . . . . .
C219 C 0.7750(2) 0.9526(2) -0.09624(5) 0.0276(5) Uani 1 1 d . . . . .
H219 H 0.8312 0.9680 -0.1099 0.033 Uiso 1 1 calc R . . . .
C220 C 0.8014(3) 1.0246(2) -0.07421(5) 0.0365(6) Uani 1 1 d . . . . .
H220 H 0.8755 1.0895 -0.0727 0.044 Uiso 1 1 calc R . . . .
C221 C 0.7180(3) 1.0026(3) -0.05353(6) 0.0409(6) Uani 1 1 d . . . . .
H221 H 0.7364 1.0532 -0.0383 0.049 Uiso 1 1 calc R . . . .
C222 C 0.6133(3) 0.9103(3) -0.05543(5) 0.0343(6) Uani 1 1 d . . . . .
H222 H 0.5590 0.8960 -0.0413 0.041 Uiso 1 1 calc R . . . .
C223 C 0.5822(2) 0.8339(2) -0.07799(4) 0.0260(5) Uani 1 1 d . . . . .
C224 C 0.4715(2) 0.7388(2) -0.08076(5) 0.0302(5) Uani 1 1 d . . . . .
H224 H 0.4154 0.7254 -0.0672 0.036 Uiso 1 1 calc R . . . .
C225 C 0.4437(2) 0.6657(2) -0.10261(5) 0.0299(5) Uani 1 1 d . . . . .
H225 H 0.3694 0.6010 -0.1039 0.036 Uiso 1 1 calc R . . . .
C226 C 0.5258(2) 0.6865(2) -0.12329(4) 0.0228(4) Uani 1 1 d . . . . .
O101 O 0.15782(15) -0.04200(16) -0.14864(4) 0.0291(4) Uani 1 1 d . . . . .
C102 C 0.1480(3) -0.1517(2) -0.14376(6) 0.0374(6) Uani 1 1 d . . . . .
H10A H 0.1284 -0.1957 -0.1612 0.045 Uiso 1 1 calc R . . . .
H10B H 0.0865 -0.1953 -0.1302 0.045 Uiso 1 1 calc R . . . .
C103 C 0.2571(3) -0.1345(2) -0.13308(6) 0.0371(6) Uani 1 1 d . . . . .
C104 C 0.3500(3) -0.0979(3) -0.12400(6) 0.0376(6) Uani 1 1 d . . . . .
C105 C 0.4669(3) -0.0218(3) -0.11435(6) 0.0375(6) Uani 1 1 d . . . . .
H10C H 0.4770 -0.0447 -0.0956 0.045 Uiso 1 1 calc R . . . .
H10D H 0.5219 -0.0267 -0.1269 0.045 Uiso 1 1 calc R . . . .
O106 O 0.48709(15) 0.09336(17) -0.11381(3) 0.0304(4) Uani 1 1 d . . . . .
C107 C 0.4734(2) 0.1332(2) -0.13910(5) 0.0280(5) Uani 1 1 d . . . . .
C108 C 0.5582(2) 0.1623(3) -0.15954(6) 0.0399(6) Uani 1 1 d . . . . .
H108 H 0.6206 0.1506 -0.1561 0.048 Uiso 1 1 calc R . . . .
C109 C 0.5503(2) 0.2072(3) -0.18415(6) 0.0447(7) Uani 1 1 d . . . . .
H109 H 0.6074 0.2262 -0.1978 0.054 Uiso 1 1 calc R . . . .
C110 C 0.4584(2) 0.2258(2) -0.18951(5) 0.0343(6) Uani 1 1 d . . . . .
C111 C 0.4478(3) 0.2716(3) -0.21513(5) 0.0436(7) Uani 1 1 d . . . . .
H111 H 0.5038 0.2903 -0.2291 0.052 Uiso 1 1 calc R . . . .
C112 C 0.3590(3) 0.2890(3) -0.21988(6) 0.0454(8) Uani 1 1 d . . . . .
H112 H 0.3524 0.3183 -0.2372 0.055 Uiso 1 1 calc R . . . .
C113 C 0.2763(3) 0.2636(2) -0.19915(5) 0.0375(6) Uani 1 1 d . . . . .
H113 H 0.2159 0.2786 -0.2024 0.045 Uiso 1 1 calc R . . . .
C114 C 0.2822(2) 0.2175(2) -0.17439(5) 0.0285(5) Uani 1 1 d . . . . .
H114 H 0.2250 0.1993 -0.1608 0.034 Uiso 1 1 calc R . . . .
C115 C 0.3730(2) 0.1967(2) -0.16896(4) 0.0245(5) Uani 1 1 d . . . . .
C116 C 0.3816(2) 0.1480(2) -0.14339(4) 0.0222(4) Uani 1 1 d . . . . .
C117 C 0.29220(19) 0.1172(2) -0.12179(4) 0.0210(4) Uani 1 1 d . . . . .
C118 C 0.3175(2) 0.1864(2) -0.09761(5) 0.0228(4) Uani 1 1 d . . . . .
C119 C 0.4275(2) 0.2808(2) -0.09267(5) 0.0299(5) Uani 1 1 d . . . . .
H119 H 0.4858 0.3016 -0.1061 0.036 Uiso 1 1 calc R . . . .
C120 C 0.4506(3) 0.3427(2) -0.06861(6) 0.0411(6) Uani 1 1 d . . . . .
H120 H 0.5247 0.4060 -0.0656 0.049 Uiso 1 1 calc R . . . .
C121 C 0.3655(3) 0.3133(3) -0.04844(6) 0.0461(7) Uani 1 1 d . . . . .
H121 H 0.3830 0.3551 -0.0316 0.055 Uiso 1 1 calc R . . . .
C122 C 0.2584(3) 0.2252(3) -0.05290(5) 0.0387(6) Uani 1 1 d . . . . .
H122 H 0.2012 0.2073 -0.0393 0.046 Uiso 1 1 calc R . . . .
C123 C 0.2302(2) 0.1593(2) -0.07759(5) 0.0274(5) Uani 1 1 d . . . . .
C124 C 0.1195(2) 0.0675(2) -0.08269(5) 0.0316(5) Uani 1 1 d . . . . .
H124 H 0.0601 0.0519 -0.0699 0.038 Uiso 1 1 calc R . . . .
C125 C 0.0963(2) 0.0008(2) -0.10560(5) 0.0289(5) Uani 1 1 d . . . . .
H125 H 0.0218 -0.0618 -0.1085 0.035 Uiso 1 1 calc R . . . .
C126 C 0.1842(2) 0.0257(2) -0.12498(5) 0.0239(4) 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
O301 C302 1.449(3) . ?
O301 C326 1.390(3) . ?
C302 H30A 0.9900 . ?
C302 H30B 0.9900 . ?
C302 C303 1.469(4) . ?
C303 C304 1.193(4) . ?
C304 C305 1.463(4) . ?
C305 H30C 0.9900 . ?
C305 H30D 0.9900 . ?
C305 O306 1.444(3) . ?
O306 C307 1.399(3) . ?
C307 C308 1.414(3) . ?
C307 C316 1.369(3) . ?
C308 H308 0.9500 . ?
C308 C309 1.365(4) . ?
C309 H309 0.9500 . ?
C309 C310 1.418(4) . ?
C310 C311 1.422(4) . ?
C310 C315 1.426(3) . ?
C311 H311 0.9500 . ?
C311 C312 1.359(5) . ?
C312 H312 0.9500 . ?
C312 C313 1.413(4) . ?
C313 H313 0.9500 . ?
C313 C314 1.372(3) . ?
C314 H314 0.9500 . ?
C314 C315 1.414(4) . ?
C315 C316 1.431(3) . ?
C316 C317 1.495(3) . ?
C317 C318 1.431(3) . ?
C317 C326 1.378(3) . ?
C318 C319 1.414(4) . ?
C318 C323 1.426(3) . ?
C319 H319 0.9500 . ?
C319 C320 1.377(3) . ?
C320 H320 0.9500 . ?
C320 C321 1.403(4) . ?
C321 H321 0.9500 . ?
C321 C322 1.358(5) . ?
C322 H322 0.9500 . ?
C322 C323 1.421(4) . ?
C323 C324 1.426(4) . ?
C324 H324 0.9500 . ?
C324 C325 1.360(4) . ?
C325 H325 0.9500 . ?
C325 C326 1.412(3) . ?
O201 C202 1.444(3) . ?
O201 C226 1.393(3) . ?
C202 H20A 0.9900 . ?
C202 H20B 0.9900 . ?
C202 C203 1.469(4) . ?
C203 C204 1.189(4) . ?
C204 C205 1.464(4) . ?
C205 H20C 0.9900 . ?
C205 H20D 0.9900 . ?
C205 O206 1.449(3) . ?
O206 C207 1.389(3) . ?
C207 C208 1.416(3) . ?
C207 C216 1.369(3) . ?
C208 H208 0.9500 . ?
C208 C209 1.354(4) . ?
C209 H209 0.9500 . ?
C209 C210 1.417(4) . ?
C210 C211 1.424(4) . ?
C210 C215 1.420(3) . ?
C211 H211 0.9500 . ?
C211 C212 1.350(5) . ?
C212 H212 0.9500 . ?
C212 C213 1.417(5) . ?
C213 H213 0.9500 . ?
C213 C214 1.374(4) . ?
C214 H214 0.9500 . ?
C214 C215 1.410(4) . ?
C215 C216 1.439(3) . ?
C216 C217 1.495(3) . ?
C217 C218 1.427(3) . ?
C217 C226 1.379(3) . ?
C218 C219 1.421(4) . ?
C218 C223 1.430(3) . ?
C219 H219 0.9500 . ?
C219 C220 1.366(4) . ?
C220 H220 0.9500 . ?
C220 C221 1.424(4) . ?
C221 H221 0.9500 . ?
C221 C222 1.346(5) . ?
C222 H222 0.9500 . ?
C222 C223 1.414(3) . ?
C223 C224 1.412(4) . ?
C224 H224 0.9500 . ?
C224 C225 1.366(4) . ?
C225 H225 0.9500 . ?
C225 C226 1.415(3) . ?
O101 C102 1.443(3) . ?
O101 C126 1.396(3) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C102 C103 1.470(4) . ?
C103 C104 1.183(4) . ?
C104 C105 1.467(4) . ?
C105 H10C 0.9900 . ?
C105 H10D 0.9900 . ?
C105 O106 1.443(4) . ?
O106 C107 1.386(3) . ?
C107 C108 1.413(3) . ?
C107 C116 1.370(3) . ?
C108 H108 0.9500 . ?
C108 C109 1.364(4) . ?
C109 H109 0.9500 . ?
C109 C110 1.412(5) . ?
C110 C111 1.425(4) . ?
C110 C115 1.423(3) . ?
C111 H111 0.9500 . ?
C111 C112 1.355(5) . ?
C112 H112 0.9500 . ?
C112 C113 1.412(5) . ?
C113 H113 0.9500 . ?
C113 C114 1.371(3) . ?
C114 H114 0.9500 . ?
C114 C115 1.417(4) . ?
C115 C116 1.433(3) . ?
C116 C117 1.492(3) . ?
C117 C118 1.430(3) . ?
C117 C126 1.374(3) . ?
C118 C119 1.416(4) . ?
C118 C123 1.427(3) . ?
C119 H119 0.9500 . ?
C119 C120 1.376(4) . ?
C120 H120 0.9500 . ?
C120 C121 1.407(5) . ?
C121 H121 0.9500 . ?
C121 C122 1.357(5) . ?
C122 H122 0.9500 . ?
C122 C123 1.424(4) . ?
C123 C124 1.410(4) . ?
C124 H124 0.9500 . ?
C124 C125 1.363(4) . ?
C125 H125 0.9500 . ?
C125 C126 1.417(3) . ?

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
C326 O301 C302 114.19(19) . . ?
O301 C302 H30A 110.2 . . ?
O301 C302 H30B 110.2 . . ?
O301 C302 C303 107.7(2) . . ?
H30A C302 H30B 108.5 . . ?
C303 C302 H30A 110.2 . . ?
C303 C302 H30B 110.2 . . ?
C304 C303 C302 164.0(3) . . ?
C303 C304 C305 165.9(3) . . ?
C304 C305 H30C 109.8 . . ?
C304 C305 H30D 109.8 . . ?
H30C C305 H30D 108.2 . . ?
O306 C305 C304 109.4(2) . . ?
O306 C305 H30C 109.8 . . ?
O306 C305 H30D 109.8 . . ?
C307 O306 C305 114.01(19) . . ?
O306 C307 C308 118.0(2) . . ?
C316 C307 O306 119.9(2) . . ?
C316 C307 C308 121.9(2) . . ?
C307 C308 H308 120.1 . . ?
C309 C308 C307 119.7(2) . . ?
C309 C308 H308 120.1 . . ?
C308 C309 H309 119.5 . . ?
C308 C309 C310 120.9(2) . . ?
C310 C309 H309 119.5 . . ?
C309 C310 C311 121.8(2) . . ?
C309 C310 C315 119.0(2) . . ?
C311 C310 C315 119.2(2) . . ?
C310 C311 H311 119.6 . . ?
C312 C311 C310 120.9(3) . . ?
C312 C311 H311 119.6 . . ?
C311 C312 H312 120.0 . . ?
C311 C312 C313 120.0(2) . . ?
C313 C312 H312 120.0 . . ?
C312 C313 H313 119.7 . . ?
C314 C313 C312 120.7(3) . . ?
C314 C313 H313 119.7 . . ?
C313 C314 H314 119.6 . . ?
C313 C314 C315 120.8(2) . . ?
C315 C314 H314 119.6 . . ?
C310 C315 C316 119.3(2) . . ?
C314 C315 C310 118.5(2) . . ?
C314 C315 C316 122.2(2) . . ?
C307 C316 C315 119.1(2) . . ?
C307 C316 C317 121.0(2) . . ?
C315 C316 C317 119.8(2) . . ?
C318 C317 C316 119.1(2) . . ?
C326 C317 C316 122.0(2) . . ?
C326 C317 C318 118.9(2) . . ?
C319 C318 C317 122.1(2) . . ?
C319 C318 C323 118.3(2) . . ?
C323 C318 C317 119.5(2) . . ?
C318 C319 H319 119.6 . . ?
C320 C319 C318 120.7(2) . . ?
C320 C319 H319 119.6 . . ?
C319 C320 H320 119.7 . . ?
C319 C320 C321 120.7(3) . . ?
C321 C320 H320 119.7 . . ?
C320 C321 H321 119.9 . . ?
C322 C321 C320 120.2(3) . . ?
C322 C321 H321 119.9 . . ?
C321 C322 H322 119.5 . . ?
C321 C322 C323 120.9(3) . . ?
C323 C322 H322 119.5 . . ?
C318 C323 C324 118.9(2) . . ?
C322 C323 C318 119.1(3) . . ?
C322 C323 C324 121.9(2) . . ?
C323 C324 H324 119.7 . . ?
C325 C324 C323 120.7(2) . . ?
C325 C324 H324 119.7 . . ?
C324 C325 H325 119.9 . . ?
C324 C325 C326 120.3(3) . . ?
C326 C325 H325 119.9 . . ?
O301 C326 C325 119.0(2) . . ?
C317 C326 O301 119.3(2) . . ?
C317 C326 C325 121.6(2) . . ?
C226 O201 C202 114.44(19) . . ?
O201 C202 H20A 109.8 . . ?
O201 C202 H20B 109.8 . . ?
O201 C202 C203 109.4(2) . . ?
H20A C202 H20B 108.2 . . ?
C203 C202 H20A 109.8 . . ?
C203 C202 H20B 109.8 . . ?
C204 C203 C202 166.9(3) . . ?
C203 C204 C205 163.0(3) . . ?
C204 C205 H20C 110.1 . . ?
C204 C205 H20D 110.1 . . ?
H20C C205 H20D 108.4 . . ?
O206 C205 C204 107.9(2) . . ?
O206 C205 H20C 110.1 . . ?
O206 C205 H20D 110.1 . . ?
C207 O206 C205 115.08(18) . . ?
O206 C207 C208 118.8(2) . . ?
C216 C207 O206 119.7(2) . . ?
C216 C207 C208 121.4(2) . . ?
C207 C208 H208 119.9 . . ?
C209 C208 C207 120.3(3) . . ?
C209 C208 H208 119.9 . . ?
C208 C209 H209 119.6 . . ?
C208 C209 C210 120.8(2) . . ?
C210 C209 H209 119.6 . . ?
C209 C210 C211 121.9(3) . . ?
C209 C210 C215 119.2(2) . . ?
C215 C210 C211 118.9(3) . . ?
C210 C211 H211 119.4 . . ?
C212 C211 C210 121.2(3) . . ?
C212 C211 H211 119.4 . . ?
C211 C212 H212 120.0 . . ?
C211 C212 C213 120.0(3) . . ?
C213 C212 H212 120.0 . . ?
C212 C213 H213 119.8 . . ?
C214 C213 C212 120.4(3) . . ?
C214 C213 H213 119.8 . . ?
C213 C214 H214 119.7 . . ?
C213 C214 C215 120.6(3) . . ?
C215 C214 H214 119.7 . . ?
C210 C215 C216 119.1(2) . . ?
C214 C215 C210 118.9(2) . . ?
C214 C215 C216 122.1(2) . . ?
C207 C216 C215 119.0(2) . . ?
C207 C216 C217 122.3(2) . . ?
C215 C216 C217 118.6(2) . . ?
C218 C217 C216 119.9(2) . . ?
C226 C217 C216 120.9(2) . . ?
C226 C217 C218 118.9(2) . . ?
C217 C218 C223 119.6(2) . . ?
C219 C218 C217 122.1(2) . . ?
C219 C218 C223 118.2(2) . . ?
C218 C219 H219 119.5 . . ?
C220 C219 C218 121.0(2) . . ?
C220 C219 H219 119.5 . . ?
C219 C220 H220 120.0 . . ?
C219 C220 C221 120.1(3) . . ?
C221 C220 H220 120.0 . . ?
C220 C221 H221 119.9 . . ?
C222 C221 C220 120.3(2) . . ?
C222 C221 H221 119.9 . . ?
C221 C222 H222 119.3 . . ?
C221 C222 C223 121.5(2) . . ?
C223 C222 H222 119.3 . . ?
C222 C223 C218 119.0(2) . . ?
C224 C223 C218 118.9(2) . . ?
C224 C223 C222 122.2(2) . . ?
C223 C224 H224 119.4 . . ?
C225 C224 C223 121.1(2) . . ?
C225 C224 H224 119.4 . . ?
C224 C225 H225 120.1 . . ?
C224 C225 C226 119.9(2) . . ?
C226 C225 H225 120.1 . . ?
O201 C226 C225 118.2(2) . . ?
C217 C226 O201 120.1(2) . . ?
C217 C226 C225 121.6(2) . . ?
C126 O101 C102 113.79(19) . . ?
O101 C102 H10A 109.9 . . ?
O101 C102 H10B 109.9 . . ?
O101 C102 C103 109.1(2) . . ?
H10A C102 H10B 108.3 . . ?
C103 C102 H10A 109.9 . . ?
C103 C102 H10B 109.9 . . ?
C104 C103 C102 166.3(3) . . ?
C103 C104 C105 163.8(3) . . ?
C104 C105 H10C 110.0 . . ?
C104 C105 H10D 110.0 . . ?
H10C C105 H10D 108.3 . . ?
O106 C105 C104 108.7(2) . . ?
O106 C105 H10C 110.0 . . ?
O106 C105 H10D 110.0 . . ?
C107 O106 C105 114.52(19) . . ?
O106 C107 C108 118.5(2) . . ?
C116 C107 O106 119.9(2) . . ?
C116 C107 C108 121.5(2) . . ?
C107 C108 H108 120.0 . . ?
C109 C108 C107 120.1(3) . . ?
C109 C108 H108 120.0 . . ?
C108 C109 H109 119.6 . . ?
C108 C109 C110 120.8(2) . . ?
C110 C109 H109 119.6 . . ?
C109 C110 C111 121.8(3) . . ?
C109 C110 C115 119.3(2) . . ?
C115 C110 C111 118.9(3) . . ?
C110 C111 H111 119.5 . . ?
C112 C111 C110 121.0(3) . . ?
C112 C111 H111 119.5 . . ?
C111 C112 H112 119.9 . . ?
C111 C112 C113 120.1(3) . . ?
C113 C112 H112 119.9 . . ?
C112 C113 H113 119.6 . . ?
C114 C113 C112 120.8(3) . . ?
C114 C113 H113 119.6 . . ?
C113 C114 H114 119.8 . . ?
C113 C114 C115 120.4(3) . . ?
C115 C114 H114 119.8 . . ?
C110 C115 C116 119.2(2) . . ?
C114 C115 C110 118.8(2) . . ?
C114 C115 C116 122.0(2) . . ?
C107 C116 C115 119.1(2) . . ?
C107 C116 C117 121.4(2) . . ?
C115 C116 C117 119.5(2) . . ?
C118 C117 C116 119.6(2) . . ?
C126 C117 C116 121.5(2) . . ?
C126 C117 C118 118.8(2) . . ?
C119 C118 C117 121.9(2) . . ?
C119 C118 C123 118.7(2) . . ?
C123 C118 C117 119.3(2) . . ?
C118 C119 H119 119.7 . . ?
C120 C119 C118 120.6(3) . . ?
C120 C119 H119 119.7 . . ?
C119 C120 H120 119.7 . . ?
C119 C120 C121 120.6(3) . . ?
C121 C120 H120 119.7 . . ?
C120 C121 H121 119.9 . . ?
C122 C121 C120 120.2(3) . . ?
C122 C121 H121 119.9 . . ?
C121 C122 H122 119.4 . . ?
C121 C122 C123 121.2(3) . . ?
C123 C122 H122 119.4 . . ?
C122 C123 C118 118.6(2) . . ?
C124 C123 C118 119.2(2) . . ?
C124 C123 C122 122.2(2) . . ?
C123 C124 H124 119.4 . . ?
C125 C124 C123 121.2(2) . . ?
C125 C124 H124 119.4 . . ?
C124 C125 H125 120.3 . . ?
C124 C125 C126 119.5(2) . . ?
C126 C125 H125 120.3 . . ?
O101 C126 C125 118.5(2) . . ?
C117 C126 O101 119.4(2) . . ?
C117 C126 C125 121.9(2) . . ?

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
O301 C302 C303 C304 11.2(12) . . . . ?
C302 O301 C326 C317 110.6(3) . . . . ?
C302 O301 C326 C325 -72.0(3) . . . . ?
C302 C303 C304 C305 -21(2) . . . . ?
C303 C304 C305 O306 19.3(13) . . . . ?
C304 C305 O306 C307 -61.6(3) . . . . ?
C305 O306 C307 C308 -78.6(3) . . . . ?
C305 O306 C307 C316 105.5(2) . . . . ?
O306 C307 C308 C309 -175.9(2) . . . . ?
O306 C307 C316 C315 177.1(2) . . . . ?
O306 C307 C316 C317 2.1(3) . . . . ?
C307 C308 C309 C310 -1.5(4) . . . . ?
C307 C316 C317 C318 72.6(3) . . . . ?
C307 C316 C317 C326 -109.1(3) . . . . ?
C308 C307 C316 C315 1.3(3) . . . . ?
C308 C307 C316 C317 -173.7(2) . . . . ?
C308 C309 C310 C311 -179.5(2) . . . . ?
C308 C309 C310 C315 1.6(4) . . . . ?
C309 C310 C311 C312 -179.6(3) . . . . ?
C309 C310 C315 C314 180.0(2) . . . . ?
C309 C310 C315 C316 -0.3(3) . . . . ?
C310 C311 C312 C313 0.1(4) . . . . ?
C310 C315 C316 C307 -1.1(3) . . . . ?
C310 C315 C316 C317 173.9(2) . . . . ?
C311 C310 C315 C314 1.0(3) . . . . ?
C311 C310 C315 C316 -179.3(2) . . . . ?
C311 C312 C313 C314 0.3(5) . . . . ?
C312 C313 C314 C315 0.1(4) . . . . ?
C313 C314 C315 C310 -0.7(4) . . . . ?
C313 C314 C315 C316 179.6(2) . . . . ?
C314 C315 C316 C307 178.6(2) . . . . ?
C314 C315 C316 C317 -6.4(3) . . . . ?
C315 C310 C311 C312 -0.7(4) . . . . ?
C315 C316 C317 C318 -102.3(2) . . . . ?
C315 C316 C317 C326 76.0(3) . . . . ?
C316 C307 C308 C309 0.0(4) . . . . ?
C316 C317 C318 C319 -0.6(3) . . . . ?
C316 C317 C318 C323 -180.0(2) . . . . ?
C316 C317 C326 O301 -4.0(3) . . . . ?
C316 C317 C326 C325 178.7(2) . . . . ?
C317 C318 C319 C320 -179.1(2) . . . . ?
C317 C318 C323 C322 178.5(2) . . . . ?
C317 C318 C323 C324 0.4(3) . . . . ?
C318 C317 C326 O301 174.4(2) . . . . ?
C318 C317 C326 C325 -3.0(3) . . . . ?
C318 C319 C320 C321 1.2(4) . . . . ?
C318 C323 C324 C325 -1.3(4) . . . . ?
C319 C318 C323 C322 -0.9(4) . . . . ?
C319 C318 C323 C324 -178.9(2) . . . . ?
C319 C320 C321 C322 -1.9(4) . . . . ?
C320 C321 C322 C323 1.2(5) . . . . ?
C321 C322 C323 C318 0.1(4) . . . . ?
C321 C322 C323 C324 178.1(3) . . . . ?
C322 C323 C324 C325 -179.3(3) . . . . ?
C323 C318 C319 C320 0.2(3) . . . . ?
C323 C324 C325 C326 0.1(4) . . . . ?
C324 C325 C326 O301 -175.2(3) . . . . ?
C324 C325 C326 C317 2.1(4) . . . . ?
C326 O301 C302 C303 -58.9(3) . . . . ?
C326 C317 C318 C319 -179.0(2) . . . . ?
C326 C317 C318 C323 1.6(3) . . . . ?
O201 C202 C203 C204 19.9(15) . . . . ?
C202 O201 C226 C217 104.8(2) . . . . ?
C202 O201 C226 C225 -79.8(3) . . . . ?
C202 C203 C204 C205 -21(2) . . . . ?
C203 C204 C205 O206 10.0(11) . . . . ?
C204 C205 O206 C207 -57.4(3) . . . . ?
C205 O206 C207 C208 -72.0(3) . . . . ?
C205 O206 C207 C216 111.0(3) . . . . ?
O206 C207 C208 C209 -173.6(3) . . . . ?
O206 C207 C216 C215 171.7(2) . . . . ?
O206 C207 C216 C217 -5.7(3) . . . . ?
C207 C208 C209 C210 1.3(5) . . . . ?
C207 C216 C217 C218 78.2(3) . . . . ?
C207 C216 C217 C226 -107.9(2) . . . . ?
C208 C207 C216 C215 -5.2(3) . . . . ?
C208 C207 C216 C217 177.4(2) . . . . ?
C208 C209 C210 C211 176.9(3) . . . . ?
C208 C209 C210 C215 -3.9(4) . . . . ?
C209 C210 C211 C212 179.7(3) . . . . ?
C209 C210 C215 C214 -178.8(2) . . . . ?
C209 C210 C215 C216 2.0(4) . . . . ?
C210 C211 C212 C213 -0.2(5) . . . . ?
C210 C215 C216 C207 2.4(3) . . . . ?
C210 C215 C216 C217 180.0(2) . . . . ?
C211 C210 C215 C214 0.4(4) . . . . ?
C211 C210 C215 C216 -178.7(2) . . . . ?
C211 C212 C213 C214 -1.2(4) . . . . ?
C212 C213 C214 C215 2.2(4) . . . . ?
C213 C214 C215 C210 -1.7(4) . . . . ?
C213 C214 C215 C216 177.3(2) . . . . ?
C214 C215 C216 C207 -176.7(2) . . . . ?
C214 C215 C216 C217 0.9(3) . . . . ?
C215 C210 C211 C212 0.5(4) . . . . ?
C215 C216 C217 C218 -99.3(2) . . . . ?
C215 C216 C217 C226 74.6(3) . . . . ?
C216 C207 C208 C209 3.4(4) . . . . ?
C216 C217 C218 C219 -6.1(3) . . . . ?
C216 C217 C218 C223 172.9(2) . . . . ?
C216 C217 C226 O201 2.7(3) . . . . ?
C216 C217 C226 C225 -172.6(2) . . . . ?
C217 C218 C219 C220 178.8(2) . . . . ?
C217 C218 C223 C222 -179.2(2) . . . . ?
C217 C218 C223 C224 -0.5(3) . . . . ?
C218 C217 C226 O201 176.67(19) . . . . ?
C218 C217 C226 C225 1.4(3) . . . . ?
C218 C219 C220 C221 0.0(4) . . . . ?
C218 C223 C224 C225 1.9(4) . . . . ?
C219 C218 C223 C222 -0.2(3) . . . . ?
C219 C218 C223 C224 178.5(2) . . . . ?
C219 C220 C221 C222 0.6(5) . . . . ?
C220 C221 C222 C223 -1.0(5) . . . . ?
C221 C222 C223 C218 0.8(4) . . . . ?
C221 C222 C223 C224 -177.9(3) . . . . ?
C222 C223 C224 C225 -179.4(2) . . . . ?
C223 C218 C219 C220 -0.2(4) . . . . ?
C223 C224 C225 C226 -1.6(4) . . . . ?
C224 C225 C226 O201 -175.4(2) . . . . ?
C224 C225 C226 C217 -0.1(4) . . . . ?
C226 O201 C202 C203 -61.3(3) . . . . ?
C226 C217 C218 C219 179.9(2) . . . . ?
C226 C217 C218 C223 -1.1(3) . . . . ?
O101 C102 C103 C104 10.8(15) . . . . ?
C102 O101 C126 C117 106.1(3) . . . . ?
C102 O101 C126 C125 -77.1(3) . . . . ?
C102 C103 C104 C105 -11(2) . . . . ?
C103 C104 C105 O106 9.0(13) . . . . ?
C104 C105 O106 C107 -58.7(3) . . . . ?
C105 O106 C107 C108 -74.0(3) . . . . ?
C105 O106 C107 C116 108.7(3) . . . . ?
O106 C107 C108 C109 -176.7(3) . . . . ?
O106 C107 C116 C115 175.7(2) . . . . ?
O106 C107 C116 C117 -2.8(4) . . . . ?
C107 C108 C109 C110 0.3(5) . . . . ?
C107 C116 C117 C118 72.5(3) . . . . ?
C107 C116 C117 C126 -109.8(3) . . . . ?
C108 C107 C116 C115 -1.5(4) . . . . ?
C108 C107 C116 C117 180.0(2) . . . . ?
C108 C109 C110 C111 -179.4(3) . . . . ?
C108 C109 C110 C115 -0.3(5) . . . . ?
C109 C110 C111 C112 -179.9(3) . . . . ?
C109 C110 C115 C114 179.0(3) . . . . ?
C109 C110 C115 C116 -0.7(4) . . . . ?
C110 C111 C112 C113 1.2(5) . . . . ?
C110 C115 C116 C107 1.6(3) . . . . ?
C110 C115 C116 C117 -179.9(2) . . . . ?
C111 C110 C115 C114 -1.8(4) . . . . ?
C111 C110 C115 C116 178.5(2) . . . . ?
C111 C112 C113 C114 -2.3(5) . . . . ?
C112 C113 C114 C115 1.3(4) . . . . ?
C113 C114 C115 C110 0.7(4) . . . . ?
C113 C114 C115 C116 -179.6(2) . . . . ?
C114 C115 C116 C107 -178.1(2) . . . . ?
C114 C115 C116 C117 0.5(3) . . . . ?
C115 C110 C111 C112 0.9(4) . . . . ?
C115 C116 C117 C118 -106.0(2) . . . . ?
C115 C116 C117 C126 71.6(3) . . . . ?
C116 C107 C108 C109 0.6(5) . . . . ?
C116 C117 C118 C119 -3.5(3) . . . . ?
C116 C117 C118 C123 177.4(2) . . . . ?
C116 C117 C126 O101 1.6(3) . . . . ?
C116 C117 C126 C125 -175.1(2) . . . . ?
C117 C118 C119 C120 -177.0(2) . . . . ?
C117 C118 C123 C122 176.6(2) . . . . ?
C117 C118 C123 C124 -2.6(3) . . . . ?
C118 C117 C126 O101 179.3(2) . . . . ?
C118 C117 C126 C125 2.6(3) . . . . ?
C118 C119 C120 C121 0.2(4) . . . . ?
C118 C123 C124 C125 3.6(4) . . . . ?
C119 C118 C123 C122 -2.6(3) . . . . ?
C119 C118 C123 C124 178.2(2) . . . . ?
C119 C120 C121 C122 -2.0(5) . . . . ?
C120 C121 C122 C123 1.5(5) . . . . ?
C121 C122 C123 C118 0.8(4) . . . . ?
C121 C122 C123 C124 -180.0(3) . . . . ?
C122 C123 C124 C125 -175.6(2) . . . . ?
C123 C118 C119 C120 2.1(4) . . . . ?
C123 C124 C125 C126 -1.5(4) . . . . ?
C124 C125 C126 O101 -178.4(2) . . . . ?
C124 C125 C126 C117 -1.7(4) . . . . ?
C126 O101 C102 C103 -60.2(3) . . . . ?
C126 C117 C118 C119 178.8(2) . . . . ?
C126 C117 C118 C123 -0.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3330(14)
2 0.6670(14)

