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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bob0320
_database_code_depnum_ccdc_archive 'CCDC 1921425'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H12 Br2 N2 O6'
_chemical_formula_sum            'C26 H12 Br2 N2 O6'
_chemical_formula_weight         608.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c26 h12 Br2 n2 o6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.3550(4)
_cell_length_b                   12.9923(7)
_cell_length_c                   24.5807(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2348.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    295
_cell_measurement_theta_max      23.8200
_cell_measurement_theta_min      3.1950
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    3.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26618
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.626
_diffrn_reflns_theta_min         2.891
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  96.00   1.00   30.00    --    8.25   0.00-120.00  176
  2  ω    -68.00  41.00   1.00   30.00    --    8.25 -77.00  60.00  109
  3  ω    -20.00  19.00   1.00   30.00    --   -8.02 -99.00-120.00   39
  4  ω    -66.00  33.00   1.00   30.00    --    8.25 -38.00 150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001592000
_diffrn_orient_matrix_UB_12      0.0182098000
_diffrn_orient_matrix_UB_13      0.0272019000
_diffrn_orient_matrix_UB_21      0.0544532000
_diffrn_orient_matrix_UB_22      -0.0425306000
_diffrn_orient_matrix_UB_23      0.0079588000
_diffrn_orient_matrix_UB_31      0.0796021000
_diffrn_orient_matrix_UB_32      0.0289929000
_diffrn_orient_matrix_UB_33      -0.0054004000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                3930
_reflns_number_total             5216
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.027
_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)+(0.0377P)²+1.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C17(H17), C18(H18),
 C23(H23), C24(H24), C25(H25), C26(H26)
;
_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
Br1 Br -0.33800(8) 0.74448(4) 0.81292(2) 0.06597(19) Uani 1 1 d . . . . .
Br2 Br 0.33063(14) 0.79701(7) 0.54741(4) 0.1160(4) Uani 1 1 d . . . . .
O1 O 0.1076(5) 1.0034(2) 0.82676(14) 0.0489(8) Uani 1 1 d . . . . .
O2 O -0.0634(7) 1.0970(3) 0.90316(19) 0.0823(14) Uani 1 1 d . . . . .
O3 O -0.1456(7) 0.9550(4) 0.94202(19) 0.0852(14) Uani 1 1 d . . . . .
O4 O 0.3854(4) 0.5213(2) 0.67340(13) 0.0437(8) Uani 1 1 d . . . . .
O5 O 0.5669(6) 0.4272(3) 0.59882(16) 0.0671(11) Uani 1 1 d . . . . .
O6 O 0.6567(8) 0.5697(3) 0.56216(16) 0.0814(13) Uani 1 1 d . . . . .
N1 N -0.0683(6) 1.0033(4) 0.9066(2) 0.0597(13) Uani 1 1 d . . . . .
N2 N 0.5740(6) 0.5215(4) 0.59652(18) 0.0520(11) Uani 1 1 d . . . . .
C1 C 0.0248(6) 0.8428(4) 0.85524(18) 0.0424(11) Uani 1 1 d . . . . .
C2 C -0.0522(6) 0.7613(4) 0.88999(18) 0.0440(11) Uani 1 1 d . . . . .
C3 C 0.0385(8) 0.7331(5) 0.9376(2) 0.0601(14) Uani 1 1 d . . . . .
H3 H 0.146799 0.765578 0.946914 0.072 Uiso 1 1 calc R . . . .
C4 C -0.0310(11) 0.6577(5) 0.9709(2) 0.0754(19) Uani 1 1 d . . . . .
H4 H 0.031378 0.639046 1.002329 0.090 Uiso 1 1 calc R . . . .
C5 C -0.1906(11) 0.6103(5) 0.9583(3) 0.0749(18) Uani 1 1 d . . . . .
H5 H -0.237531 0.560309 0.981416 0.090 Uiso 1 1 calc R . . . .
C6 C -0.2828(9) 0.6356(5) 0.9115(3) 0.0691(17) Uani 1 1 d . . . . .
H6 H -0.391492 0.603001 0.902750 0.083 Uiso 1 1 calc R . . . .
C7 C -0.2115(7) 0.7102(4) 0.8776(2) 0.0489(12) Uani 1 1 d . . . . .
C8 C 0.0197(7) 0.9458(4) 0.8643(2) 0.0482(12) Uani 1 1 d . . . . .
C9 C 0.1777(7) 0.9329(3) 0.79069(18) 0.0431(11) Uani 1 1 d . . . . .
C10 C 0.1313(6) 0.8333(3) 0.80616(17) 0.0384(10) Uani 1 1 d . . . . .
C11 C 0.1947(5) 0.7492(3) 0.77370(16) 0.0370(9) Uani 1 1 d . . . . .
C12 C 0.1531(7) 0.6447(3) 0.78645(17) 0.0410(10) Uani 1 1 d . . . . .
H12 H 0.084602 0.630089 0.817302 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2114(7) 0.5660(4) 0.75458(18) 0.0438(11) Uani 1 1 d . . . . .
H13 H 0.182388 0.497972 0.762488 0.053 Uiso 1 1 calc R . . . .
C14 C 0.3160(7) 0.5917(3) 0.70973(17) 0.0394(10) Uani 1 1 d . . . . .
C15 C 0.3705(6) 0.6900(3) 0.69603(17) 0.0378(10) Uani 1 1 d . . . . .
C16 C 0.3051(6) 0.7748(3) 0.72783(17) 0.0367(10) Uani 1 1 d . . . . .
C17 C 0.3458(8) 0.8790(3) 0.71522(18) 0.0439(11) Uani 1 1 d . . . . .
H17 H 0.418452 0.893214 0.685169 0.053 Uiso 1 1 calc R . . . .
C18 C 0.2819(7) 0.9590(4) 0.7457(2) 0.0495(12) Uani 1 1 d . . . . .
H18 H 0.306887 1.027195 0.736885 0.059 Uiso 1 1 calc R . . . .
C19 C 0.4865(7) 0.5786(4) 0.63836(18) 0.0440(11) Uani 1 1 d . . . . .
C20 C 0.4870(6) 0.6813(4) 0.64987(17) 0.0409(10) Uani 1 1 d . . . . .
C21 C 0.6047(6) 0.7615(4) 0.62519(19) 0.0467(11) Uani 1 1 d . . . . .
C22 C 0.5556(8) 0.8205(5) 0.5810(2) 0.0625(15) Uani 1 1 d . . . . .
C23 C 0.6706(13) 0.8972(5) 0.5613(3) 0.089(2) Uani 1 1 d . . . . .
H23 H 0.636889 0.936971 0.531554 0.107 Uiso 1 1 calc R . . . .
C24 C 0.8343(12) 0.9128(6) 0.5867(4) 0.099(2) Uani 1 1 d . . . . .
H24 H 0.911704 0.963789 0.573706 0.118 Uiso 1 1 calc R . . . .
C25 C 0.8871(10) 0.8550(6) 0.6307(4) 0.095(2) Uani 1 1 d . . . . .
H25 H 0.999218 0.866688 0.647073 0.114 Uiso 1 1 calc R . . . .
C26 C 0.7737(8) 0.7801(5) 0.6505(3) 0.0713(17) Uani 1 1 d . . . . .
H26 H 0.808195 0.741523 0.680646 0.086 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
Br1 C7 1.894(5) . ?
Br2 C22 1.874(6) . ?
O1 C8 1.353(6) . ?
O1 C9 1.375(5) . ?
O2 N1 1.220(6) . ?
O3 N1 1.214(6) . ?
O4 C14 1.377(5) . ?
O4 C19 1.359(6) . ?
O5 N2 1.228(6) . ?
O6 N2 1.215(6) . ?
N1 C8 1.435(7) . ?
N2 C19 1.422(6) . ?
C1 C2 1.474(7) . ?
C1 C8 1.358(7) . ?
C1 C10 1.444(6) . ?
C2 C3 1.397(7) . ?
C2 C7 1.380(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(8) . ?
C9 C10 1.391(6) . ?
C9 C18 1.387(7) . ?
C10 C11 1.431(6) . ?
C11 C12 1.427(6) . ?
C11 C16 1.429(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(6) . ?
C14 C15 1.381(6) . ?
C15 C16 1.433(6) . ?
C15 C20 1.426(6) . ?
C16 C17 1.422(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(7) . ?
C20 C21 1.485(7) . ?
C21 C22 1.377(7) . ?
C21 C26 1.411(8) . ?
C22 C23 1.393(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.371(11) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(11) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(9) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 104.6(4) . . ?
C19 O4 C14 104.5(3) . . ?
O2 N1 C8 117.1(5) . . ?
O3 N1 O2 125.5(5) . . ?
O3 N1 C8 117.4(5) . . ?
O5 N2 C19 117.9(5) . . ?
O6 N2 O5 124.6(5) . . ?
O6 N2 C19 117.4(5) . . ?
C8 C1 C2 127.1(4) . . ?
C8 C1 C10 103.7(4) . . ?
C10 C1 C2 129.1(4) . . ?
C3 C2 C1 119.4(5) . . ?
C7 C2 C1 122.9(4) . . ?
C7 C2 C3 117.7(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(6) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.0(6) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 Br1 119.3(4) . . ?
C2 C7 C6 121.7(5) . . ?
C6 C7 Br1 119.0(4) . . ?
O1 C8 N1 115.0(4) . . ?
O1 C8 C1 114.8(4) . . ?
C1 C8 N1 130.2(5) . . ?
O1 C9 C10 110.5(4) . . ?
O1 C9 C18 123.9(4) . . ?
C18 C9 C10 125.5(4) . . ?
C9 C10 C1 106.4(4) . . ?
C9 C10 C11 118.5(4) . . ?
C11 C10 C1 135.1(4) . . ?
C12 C11 C10 122.3(4) . . ?
C12 C11 C16 121.1(4) . . ?
C16 C11 C10 116.6(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 117.0(4) . . ?
C14 C13 H13 121.5 . . ?
O4 C14 C13 124.2(4) . . ?
O4 C14 C15 110.4(4) . . ?
C15 C14 C13 125.3(4) . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 C20 107.1(4) . . ?
C20 C15 C16 134.2(4) . . ?
C11 C16 C15 116.3(4) . . ?
C17 C16 C11 120.9(4) . . ?
C17 C16 C15 122.8(4) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.2(4) . . ?
C18 C17 H17 118.9 . . ?
C9 C18 H18 121.9 . . ?
C17 C18 C9 116.2(4) . . ?
C17 C18 H18 121.9 . . ?
O4 C19 N2 114.9(4) . . ?
O4 C19 C20 113.9(4) . . ?
C20 C19 N2 131.2(5) . . ?
C15 C20 C21 128.3(4) . . ?
C19 C20 C15 104.0(4) . . ?
C19 C20 C21 127.1(4) . . ?
C22 C21 C20 124.0(5) . . ?
C22 C21 C26 118.9(5) . . ?
C26 C21 C20 117.0(5) . . ?
C21 C22 Br2 119.3(4) . . ?
C21 C22 C23 120.8(6) . . ?
C23 C22 Br2 119.9(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.8(7) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.7(7) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.7(7) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.1(7) . . ?
C25 C26 H26 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C22 C23 C24 180.0(6) . . . . ?
O1 C9 C10 C1 0.1(5) . . . . ?
O1 C9 C10 C11 -179.2(4) . . . . ?
O1 C9 C18 C17 177.8(5) . . . . ?
O2 N1 C8 O1 3.6(7) . . . . ?
O2 N1 C8 C1 -174.4(6) . . . . ?
O3 N1 C8 O1 -178.4(5) . . . . ?
O3 N1 C8 C1 3.5(9) . . . . ?
O4 C14 C15 C16 177.3(4) . . . . ?
O4 C14 C15 C20 -2.5(5) . . . . ?
O4 C19 C20 C15 -1.6(5) . . . . ?
O4 C19 C20 C21 169.8(4) . . . . ?
O5 N2 C19 O4 -7.3(7) . . . . ?
O5 N2 C19 C20 172.2(5) . . . . ?
O6 N2 C19 O4 175.5(5) . . . . ?
O6 N2 C19 C20 -5.0(8) . . . . ?
N2 C19 C20 C15 178.9(5) . . . . ?
N2 C19 C20 C21 -9.7(9) . . . . ?
C1 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C7 Br1 0.6(6) . . . . ?
C1 C2 C7 C6 -178.6(5) . . . . ?
C1 C10 C11 C12 1.2(8) . . . . ?
C1 C10 C11 C16 -177.9(5) . . . . ?
C2 C1 C8 O1 177.5(4) . . . . ?
C2 C1 C8 N1 -4.4(9) . . . . ?
C2 C1 C10 C9 -177.1(5) . . . . ?
C2 C1 C10 C11 2.0(9) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C3 C2 C7 Br1 -179.2(4) . . . . ?
C3 C2 C7 C6 1.6(7) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C5 C6 C7 Br1 179.6(4) . . . . ?
C5 C6 C7 C2 -1.2(8) . . . . ?
C7 C2 C3 C4 -0.6(8) . . . . ?
C8 O1 C9 C10 0.4(5) . . . . ?
C8 O1 C9 C18 -178.8(5) . . . . ?
C8 C1 C2 C3 -76.5(7) . . . . ?
C8 C1 C2 C7 103.7(6) . . . . ?
C8 C1 C10 C9 -0.5(5) . . . . ?
C8 C1 C10 C11 178.5(5) . . . . ?
C9 O1 C8 N1 -179.2(4) . . . . ?
C9 O1 C8 C1 -0.8(6) . . . . ?
C9 C10 C11 C12 -179.8(5) . . . . ?
C9 C10 C11 C16 1.1(6) . . . . ?
C10 C1 C2 C3 99.3(6) . . . . ?
C10 C1 C2 C7 -80.5(7) . . . . ?
C10 C1 C8 O1 0.9(6) . . . . ?
C10 C1 C8 N1 178.9(5) . . . . ?
C10 C9 C18 C17 -1.3(8) . . . . ?
C10 C11 C12 C13 178.7(5) . . . . ?
C10 C11 C16 C15 179.0(4) . . . . ?
C10 C11 C16 C17 -1.1(6) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C11 C16 C17 C18 -0.2(7) . . . . ?
C12 C11 C16 C15 0.0(6) . . . . ?
C12 C11 C16 C17 179.9(4) . . . . ?
C12 C13 C14 O4 -180.0(5) . . . . ?
C12 C13 C14 C15 2.3(8) . . . . ?
C13 C14 C15 C16 -4.7(7) . . . . ?
C13 C14 C15 C20 175.5(5) . . . . ?
C14 O4 C19 N2 179.7(4) . . . . ?
C14 O4 C19 C20 0.2(5) . . . . ?
C14 C15 C16 C11 3.3(6) . . . . ?
C14 C15 C16 C17 -176.6(4) . . . . ?
C14 C15 C20 C19 2.4(5) . . . . ?
C14 C15 C20 C21 -168.9(5) . . . . ?
C15 C16 C17 C18 179.7(5) . . . . ?
C15 C20 C21 C22 -96.9(6) . . . . ?
C15 C20 C21 C26 80.4(6) . . . . ?
C16 C11 C12 C13 -2.3(7) . . . . ?
C16 C15 C20 C19 -177.3(5) . . . . ?
C16 C15 C20 C21 11.3(8) . . . . ?
C16 C17 C18 C9 1.4(8) . . . . ?
C18 C9 C10 C1 179.3(5) . . . . ?
C18 C9 C10 C11 0.0(8) . . . . ?
C19 O4 C14 C13 -176.5(5) . . . . ?
C19 O4 C14 C15 1.5(5) . . . . ?
C19 C20 C21 C22 93.7(7) . . . . ?
C19 C20 C21 C26 -89.0(6) . . . . ?
C20 C15 C16 C11 -176.9(5) . . . . ?
C20 C15 C16 C17 3.1(8) . . . . ?
C20 C21 C22 Br2 -2.3(7) . . . . ?
C20 C21 C22 C23 177.6(5) . . . . ?
C20 C21 C26 C25 -178.3(6) . . . . ?
C21 C22 C23 C24 0.1(10) . . . . ?
C22 C21 C26 C25 -0.8(9) . . . . ?
C22 C23 C24 C25 0.0(12) . . . . ?
C23 C24 C25 C26 -0.5(13) . . . . ?
C24 C25 C26 C21 0.9(11) . . . . ?
C26 C21 C22 Br2 -179.6(4) . . . . ?
C26 C21 C22 C23 0.3(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.746
####################################################################### 
# 
# 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_b9302162
_database_code_depnum_ccdc_archive 'CCDC 1922303'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille University
France
;
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N O5, 0.35(C3 H7)'
_chemical_formula_sum            'C16.05 H12.45 N O5'
_chemical_formula_weight         299.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c30 h22 n2 o10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   15.0405(2)
_cell_length_b                   8.47920(10)
_cell_length_c                   13.84310(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.6020(10)
_cell_angle_gamma                90
_cell_volume                     1691.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10111
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.8850
_cell_measurement_theta_min      5.1270
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             623
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12262
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.857
_diffrn_reflns_theta_min         3.830
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    1.00    --  -41.07  57.00 -30.00  101
  2  ω   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00 -60.00   98
  3  ω   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00-180.00   98
  4  ω   -121.00   0.00   1.00    1.00    --  -41.07 -19.00  30.00  121
  5  ω     23.00  97.00   1.00    1.00    --   41.07-125.00  60.00   74
  6  ω     19.00 109.00   1.00    5.00    --  101.41 -94.00 -30.00   90
  7  ω     20.00 154.00   1.00    5.00    --  101.41 -15.00-180.00  134
  8  ω    100.00 178.00   1.00    5.00    --  101.41 109.00  14.00   78
  9  ω     19.00 109.00   1.00    5.00    --  101.41 -94.00  60.00   90
 10  ω     19.00 109.00   1.00    5.00    --  101.41 -94.00-150.00   90
 11  ω     28.00 117.00   1.00    5.00    --  101.41-125.00-150.00   89
 12  ω     29.00 130.00   1.00    5.00    --  101.41 -61.00-120.00  101
 13  ω     28.00 127.00   1.00    5.00    --  101.41 -45.00  60.00   99
 14  ω     49.00 178.00   1.00    5.00    --  101.41  15.00-120.00  129
 15  ω     28.00 127.00   1.00    5.00    --  101.41 -45.00   0.00   99
 16  ω     25.00 130.00   1.00    5.00    --  101.41 -30.00-120.00  105
 17  ω   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00  30.00  109
 18  ω   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00 -90.00  109
 19  ω   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00 120.00  109
 20  ω     23.00  97.00   1.00    1.00    --   41.07-125.00-150.00   74
 21  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 -90.00  102
 22  ω     72.00 174.00   1.00    5.00    --  101.41  61.00  60.00  102
 23  ω     73.00 178.00   1.00    5.00    --  101.41  30.00   0.00  105
 24  ω     72.00 123.00   1.00    5.00    --  101.41  61.00 120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575488000
_diffrn_orient_matrix_UB_12      0.1472876000
_diffrn_orient_matrix_UB_13      -0.0434195000
_diffrn_orient_matrix_UB_21      -0.0585063000
_diffrn_orient_matrix_UB_22      -0.0988249000
_diffrn_orient_matrix_UB_23      -0.0889693000
_diffrn_orient_matrix_UB_31      -0.0684783000
_diffrn_orient_matrix_UB_32      -0.0393378000
_diffrn_orient_matrix_UB_33      0.0607128000
_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         0.841
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3155
_reflns_number_total             3195
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.156
_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)+(0.1544P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C16
 1.45 with sigma of 0.02
 C20-C21
 1.45 with sigma of 0.01
 C17-C18
 1.54 with sigma of 0.02
 C20-C19
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C16 \\sim C17: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.02
C17 \\sim C18: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.02
Uanis(C17) = Uanis(C20)
Uanis(C21) = Uanis(C16)
Uanis(C19) = Uanis(C18)
4. Rigid body (RIGU) restrains
 C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C19, C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: C16(0.2) H16A(0.2) H16B(0.2) C17(0.2) H17A(0.2) H17B(0.2) C18(0.2)
 H18A(0.2) H18B(0.2) H18C(0.2) C19(0.15) H19A(0.15) H19B(0.15) H19C(0.15)
 C20(0.15) H20A(0.15) H20B(0.15) C21(0.15) H21A(0.15) H21B(0.15)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C13(H13), C14(H14)
6.d Idealised Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
6.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.43123(16) 0.4405(4) 0.74497(16) 0.0566(6) Uani 1 1 d . . . . .
O2 O 0.3846(3) 0.1443(5) 0.7465(5) 0.1185(18) Uani 1 1 d . . . . .
O3 O 0.2416(2) 0.1920(4) 0.6949(3) 0.0794(9) Uani 1 1 d . . . . .
O4 O 0.1616(3) 0.2876(5) 0.4400(6) 0.147(3) Uani 1 1 d . . . . .
O5 O 0.0326(2) 0.4211(5) 0.3971(3) 0.0882(11) Uani 1 1 d . . . . .
N1 N 0.3218(2) 0.2320(3) 0.7156(2) 0.0562(7) Uani 1 1 d . . . . .
C1 C 0.2561(2) 0.5738(4) 0.5455(2) 0.0456(7) Uani 1 1 d . . . . .
C2 C 0.2908(3) 0.7218(4) 0.5785(3) 0.0606(8) Uani 1 1 d . . . . .
C3 C 0.2360(4) 0.8564(5) 0.5518(4) 0.0779(12) Uani 1 1 d . . . . .
H3 H 0.260065 0.954618 0.575520 0.093 Uiso 1 1 calc R . . . .
C4 C 0.1479(4) 0.8443(6) 0.4914(4) 0.0785(12) Uani 1 1 d . . . . .
H4 H 0.111677 0.934490 0.473672 0.094 Uiso 1 1 calc R . . . .
C5 C 0.1114(3) 0.6985(6) 0.4560(3) 0.0707(10) Uani 1 1 d . . . . .
H5 H 0.051133 0.691538 0.413686 0.085 Uiso 1 1 calc R . . . .
C6 C 0.1645(2) 0.5619(5) 0.4832(2) 0.0528(7) Uani 1 1 d . . . . .
C7 C 0.1216(3) 0.4093(5) 0.4403(3) 0.0652(9) Uani 1 1 d . . . . .
C8 C -0.0149(3) 0.2849(9) 0.3492(5) 0.0964(17) Uani 1 1 d . . . . .
H8A H 0.020468 0.235445 0.309869 0.145 Uiso 1 1 calc GR . . . .
H8B H -0.074657 0.314717 0.305973 0.145 Uiso 1 1 calc GR . . . .
H8C H -0.022804 0.212293 0.399361 0.145 Uiso 1 1 calc GR . . . .
C9 C 0.31815(18) 0.4314(3) 0.5816(2) 0.0433(6) Uani 1 1 d . . . . .
H9 H 0.289227 0.336710 0.545405 0.052 Uiso 1 1 calc R . . . .
C10 C 0.3384(2) 0.4060(4) 0.6974(2) 0.0468(7) Uani 1 1 d . . . . .
H10 H 0.297754 0.472971 0.724051 0.056 Uiso 1 1 calc R . . . .
C11 C 0.4761(2) 0.4474(4) 0.6701(2) 0.0498(7) Uani 1 1 d . . . . .
C12 C 0.41624(19) 0.4467(4) 0.5756(2) 0.0455(7) Uani 1 1 d . . . . .
C13 C 0.5728(2) 0.4534(6) 0.6909(2) 0.0595(9) Uani 1 1 d . . . . .
H13 H 0.611322 0.457080 0.756728 0.071 Uiso 1 1 calc R . . . .
C14 C 0.6082(2) 0.4537(5) 0.6101(2) 0.0556(8) Uani 1 1 d . . . . .
H14 H 0.672204 0.455314 0.621295 0.067 Uiso 1 1 calc R . . . .
C15 C 0.54945(18) 0.4517(4) 0.5100(2) 0.0453(7) Uani 1 1 d . . . . .
C16 C 0.4546(19) 0.975(5) 0.4761(19) 0.103(6) Uani 0.2 1 d D U P A 1
H16A H 0.433319 1.082986 0.466050 0.123 Uiso 0.2 1 calc R . P A 1
H16B H 0.422035 0.923990 0.518813 0.123 Uiso 0.2 1 calc R . P A 1
C17 C 0.4303(19) 0.896(5) 0.3800(18) 0.103(6) Uani 0.2 1 d D U P A 1
H17A H 0.414685 0.786630 0.387195 0.123 Uiso 0.2 1 calc R . P A 1
H17B H 0.481218 0.900412 0.350134 0.123 Uiso 0.2 1 calc R . P A 1
C18 C 0.3422(19) 0.990(6) 0.312(2) 0.100(6) Uani 0.2 1 d D U P A 1
H18A H 0.335831 0.971011 0.242304 0.151 Uiso 0.2 1 calc R . P A 1
H18B H 0.350645 1.101248 0.325789 0.151 Uiso 0.2 1 calc R . P A 1
H18C H 0.287316 0.955295 0.328140 0.151 Uiso 0.2 1 calc R . P A 1
C19 C 0.331(3) 0.899(7) 0.321(3) 0.100(6) Uani 0.15 1 d D U P B 2
H19A H 0.311674 0.899753 0.248402 0.151 Uiso 0.15 1 calc R . P B 2
H19B H 0.282695 0.946113 0.344800 0.151 Uiso 0.15 1 calc R . P B 2
H19C H 0.341023 0.792909 0.344736 0.151 Uiso 0.15 1 calc R . P B 2
C20 C 0.421(2) 0.996(6) 0.360(3) 0.103(6) Uani 0.15 1 d D U P B 2
H20A H 0.453060 1.008515 0.308630 0.123 Uiso 0.15 1 calc R . P B 2
H20B H 0.409742 1.098874 0.384530 0.123 Uiso 0.15 1 calc R . P B 2
C21 C 0.473(3) 0.895(7) 0.442(3) 0.103(6) Uani 0.15 1 d D U P B 2
H21A H 0.520564 0.853411 0.413534 0.123 Uiso 0.15 1 calc R . P B 2
H21B H 0.430320 0.808822 0.437571 0.123 Uiso 0.15 1 calc R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.395(4) . ?
O1 C11 1.391(3) . ?
O2 N1 1.183(5) . ?
O3 N1 1.206(4) . ?
O4 C7 1.195(6) . ?
O5 C7 1.305(4) . ?
O5 C8 1.419(7) . ?
N1 C10 1.530(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.405(4) . ?
C1 C9 1.521(4) . ?
C2 C3 1.394(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(5) . ?
C6 C7 1.491(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C10 1.558(4) . ?
C9 C12 1.507(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.360(4) . ?
C11 C13 1.401(4) . ?
C12 C15 1.421(4) 2_656 ?
C13 H13 0.9300 . ?
C13 C14 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.415(4) . ?
C15 C12 1.422(4) 2_656 ?
C15 C15 1.433(5) 2_656 ?
C16 C16 1.34(5) 2_656 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.44(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.60(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 C20 1.552(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.452(14) . ?
C21 C21 1.58(7) 2_656 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C11 O1 C10 106.9(2) . . ?
C7 O5 C8 117.7(4) . . ?
O2 N1 O3 123.5(4) . . ?
O2 N1 C10 121.0(3) . . ?
O3 N1 C10 115.5(3) . . ?
C2 C1 C6 118.6(3) . . ?
C2 C1 C9 118.2(3) . . ?
C6 C1 C9 123.2(3) . . ?
C1 C2 C3 121.0(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 122.9(3) . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 117.6(3) . . ?
O4 C7 O5 121.1(4) . . ?
O4 C7 C6 126.2(3) . . ?
O5 C7 C6 112.7(4) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 H9 109.9 . . ?
C1 C9 C10 111.6(2) . . ?
C10 C9 H9 109.9 . . ?
C12 C9 C1 115.6(3) . . ?
C12 C9 H9 109.9 . . ?
C12 C9 C10 99.4(2) . . ?
O1 C10 N1 108.3(3) . . ?
O1 C10 C9 109.4(2) . . ?
O1 C10 H10 110.4 . . ?
N1 C10 C9 108.0(2) . . ?
N1 C10 H10 110.4 . . ?
C9 C10 H10 110.4 . . ?
O1 C11 C13 123.0(2) . . ?
C12 C11 O1 112.8(3) . . ?
C12 C11 C13 124.2(3) . . ?
C11 C12 C9 109.7(2) . . ?
C11 C12 C15 120.2(3) . 2_656 ?
C15 C12 C9 130.0(2) 2_656 . ?
C11 C13 H13 121.5 . . ?
C14 C13 C11 117.1(3) . . ?
C14 C13 H13 121.5 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C12 C15 C15 116.3(3) 2_656 2_656 ?
C14 C15 C12 122.9(3) . 2_656 ?
C14 C15 C15 120.8(3) . 2_656 ?
C16 C16 H16A 108.7 2_656 . ?
C16 C16 H16B 108.7 2_656 . ?
C16 C16 C17 114(3) 2_656 . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C16 C17 C18 105(3) . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
C19 C20 H20A 111.6 . . ?
C19 C20 H20B 111.6 . . ?
H20A C20 H20B 109.4 . . ?
C21 C20 C19 101(3) . . ?
C21 C20 H20A 111.6 . . ?
C21 C20 H20B 111.6 . . ?
C20 C21 C21 143(3) . 2_656 ?
C20 C21 H21A 101.3 . . ?
C20 C21 H21B 101.3 . . ?
C21 C21 H21A 101.3 2_656 . ?
C21 C21 H21B 101.3 2_656 . ?
H21A C21 H21B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C9 -2.4(4) . . . . ?
O1 C11 C12 C15 -179.4(3) . . . 2_656 ?
O1 C11 C13 C14 177.5(4) . . . . ?
O2 N1 C10 O1 -14.1(5) . . . . ?
O2 N1 C10 C9 104.2(5) . . . . ?
O3 N1 C10 O1 167.0(3) . . . . ?
O3 N1 C10 C9 -74.7(4) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C6 C7 O4 -12.2(8) . . . . ?
C1 C6 C7 O5 170.6(4) . . . . ?
C1 C9 C10 O1 -110.3(3) . . . . ?
C1 C9 C10 N1 132.1(2) . . . . ?
C1 C9 C12 C11 113.8(3) . . . . ?
C1 C9 C12 C15 -69.6(4) . . . 2_656 ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C7 177.6(3) . . . . ?
C2 C1 C9 C10 66.0(4) . . . . ?
C2 C1 C9 C12 -46.6(4) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C4 C5 C6 C7 -178.6(4) . . . . ?
C5 C6 C7 O4 165.1(7) . . . . ?
C5 C6 C7 O5 -12.1(5) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
C6 C1 C9 C10 -111.8(3) . . . . ?
C6 C1 C9 C12 135.7(3) . . . . ?
C8 O5 C7 O4 -0.4(9) . . . . ?
C8 O5 C7 C6 177.0(5) . . . . ?
C9 C1 C2 C3 -177.1(3) . . . . ?
C9 C1 C6 C5 178.1(3) . . . . ?
C9 C1 C6 C7 -4.7(5) . . . . ?
C10 O1 C11 C12 10.6(4) . . . . ?
C10 O1 C11 C13 -169.0(4) . . . . ?
C10 C9 C12 C11 -5.7(3) . . . . ?
C10 C9 C12 C15 170.8(3) . . . 2_656 ?
C11 O1 C10 N1 103.3(3) . . . . ?
C11 O1 C10 C9 -14.2(4) . . . . ?
C11 C13 C14 C15 1.4(6) . . . . ?
C12 C9 C10 O1 12.1(3) . . . . ?
C12 C9 C10 N1 -105.5(3) . . . . ?
C12 C11 C13 C14 -2.1(6) . . . . ?
C13 C11 C12 C9 177.2(3) . . . . ?
C13 C11 C12 C15 0.2(6) . . . 2_656 ?
C13 C14 C15 C12 -177.9(4) . . . 2_656 ?
C13 C14 C15 C15 1.0(5) . . . 2_656 ?
C16 C16 C17 C18 -147(2) 2_656 . . . ?
C19 C20 C21 C21 -126(8) . . . 2_656 ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.717
