# Electronic Supplementary Material (ESI) for ChemComm.
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1546720'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 N O3'
_chemical_formula_sum            'C22 H13 N O3'
_chemical_formula_weight         339.33

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.5765(2)
_cell_length_b                   19.1304(5)
_cell_length_c                   10.1094(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3940(10)
_cell_angle_gamma                90
_cell_volume                     1657.22(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      30.47

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12559
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.280
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2908
_reflns_number_gt                2683
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+1.5366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2908
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      0.884
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.22421(12) -0.02927(5) 0.52614(11) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.41131(11) 0.29644(5) 0.89968(9) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.34239(11) 0.19704(5) 0.79749(9) 0.0194(2) Uani 1 1 d . . . . .
N1 N 0.82857(15) 0.58797(6) 0.53666(12) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.25943(16) 0.02812(7) 0.57264(13) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.14833(16) 0.08676(7) 0.56892(13) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.0453 0.0795 0.5333 0.023 Uiso 1 1 calc R U . . .
C3 C 0.18906(15) 0.14959(7) 0.61427(13) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.1122 0.1853 0.6137 0.021 Uiso 1 1 calc R U . . .
C4 C 0.35091(15) 0.16669(7) 0.66638(12) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.45659(15) 0.10411(7) 0.67931(12) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.5577 0.1100 0.7198 0.022 Uiso 1 1 calc R U . . .
C6 C 0.41451(16) 0.04100(7) 0.63652(13) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.4859 0.0033 0.6473 0.024 Uiso 1 1 calc R U . . .
C7 C 0.42037(14) 0.22531(7) 0.58485(12) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.44944(14) 0.28121(7) 0.66266(12) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.40228(15) 0.26330(7) 0.79870(13) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.43608(15) 0.21552(7) 0.44084(12) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.53536(16) 0.16455(7) 0.39286(13) 0.0180(3) Uani 1 1 d . . . . .
H11 H 0.5957 0.1362 0.4528 0.022 Uiso 1 1 calc R U . . .
C12 C 0.54575(16) 0.15531(7) 0.25686(13) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.6135 0.1206 0.2243 0.024 Uiso 1 1 calc R U . . .
C13 C 0.45847(16) 0.19617(7) 0.16919(13) 0.0204(3) Uani 1 1 d . . . . .
H13 H 0.4655 0.1894 0.0765 0.024 Uiso 1 1 calc R U . . .
C14 C 0.36005(16) 0.24738(7) 0.21679(13) 0.0201(3) Uani 1 1 d . . . . .
H14 H 0.3007 0.2758 0.1564 0.024 Uiso 1 1 calc R U . . .
C15 C 0.34819(15) 0.25707(7) 0.35180(13) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.2804 0.2919 0.3838 0.021 Uiso 1 1 calc R U . . .
C16 C 0.52318(15) 0.34875(7) 0.63261(12) 0.0155(3) Uani 1 1 d . . . . .
C17 C 0.61909(15) 0.35472(7) 0.52454(13) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.6320 0.3157 0.4678 0.021 Uiso 1 1 calc R U . . .
C18 C 0.69513(16) 0.41663(7) 0.49947(13) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.7594 0.4202 0.4255 0.022 Uiso 1 1 calc R U . . .
C19 C 0.67765(16) 0.47376(7) 0.58237(13) 0.0181(3) Uani 1 1 d . . . . .
C20 C 0.58105(17) 0.46895(7) 0.68971(13) 0.0212(3) Uani 1 1 d . . . . .
H20 H 0.5680 0.5081 0.7459 0.025 Uiso 1 1 calc R U . . .
C21 C 0.50435(16) 0.40694(7) 0.71399(13) 0.0195(3) Uani 1 1 d . . . . .
H21 H 0.4382 0.4039 0.7868 0.023 Uiso 1 1 calc R U . . .
C22 C 0.76058(17) 0.53753(7) 0.55712(13) 0.0205(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2271(17) . ?
O2 C9 1.2013(16) . ?
O3 C9 1.3677(16) . ?
O3 C4 1.4517(15) . ?
N1 C22 1.1506(19) . ?
C1 C2 1.4714(19) . ?
C1 C6 1.4748(19) . ?
C2 C3 1.328(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.5001(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.5040(18) . ?
C4 C7 1.5275(18) . ?
C5 C6 1.327(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3446(18) . ?
C7 C10 1.4796(17) . ?
C8 C16 1.4758(18) . ?
C8 C9 1.4896(17) . ?
C10 C11 1.3948(19) . ?
C10 C15 1.3977(18) . ?
C11 C12 1.3927(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3853(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.3975(18) . ?
C16 C17 1.3994(18) . ?
C17 C18 1.3806(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3891(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3955(19) . ?
C19 C22 1.4403(19) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 H21 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
C9 O3 C4 110.22(9) . . ?
O1 C1 C2 121.57(13) . . ?
O1 C1 C6 121.36(13) . . ?
C2 C1 C6 117.06(12) . . ?
C3 C2 C1 121.37(12) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 123.01(12) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
O3 C4 C3 109.07(10) . . ?
O3 C4 C5 106.99(10) . . ?
C3 C4 C5 113.73(11) . . ?
O3 C4 C7 103.57(10) . . ?
C3 C4 C7 110.28(10) . . ?
C5 C4 C7 112.59(11) . . ?
C6 C5 C4 122.75(12) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 121.51(12) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C10 130.84(12) . . ?
C8 C7 C4 109.59(11) . . ?
C10 C7 C4 119.45(11) . . ?
C7 C8 C16 130.28(12) . . ?
C7 C8 C9 107.84(11) . . ?
C16 C8 C9 121.77(11) . . ?
O2 C9 O3 120.50(12) . . ?
O2 C9 C8 130.76(12) . . ?
O3 C9 C8 108.74(11) . . ?
C11 C10 C15 119.62(12) . . ?
C11 C10 C7 120.84(12) . . ?
C15 C10 C7 119.53(12) . . ?
C10 C11 C12 119.81(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.48(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.84(12) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.34(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.91(13) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C21 C16 C17 118.73(12) . . ?
C21 C16 C8 121.01(12) . . ?
C17 C16 C8 120.20(12) . . ?
C18 C17 C16 120.73(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.03(12) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 119.99(12) . . ?
C18 C19 C22 119.53(12) . . ?
C20 C19 C22 120.48(12) . . ?
C21 C20 C19 119.78(12) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 120.74(12) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N1 C22 C19 179.10(15) . . ?

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 C1 C2 C3 -177.10(13) . . . . ?
C6 C1 C2 C3 3.77(19) . . . . ?
C1 C2 C3 C4 2.9(2) . . . . ?
C9 O3 C4 C3 -119.30(11) . . . . ?
C9 O3 C4 C5 117.28(11) . . . . ?
C9 O3 C4 C7 -1.86(13) . . . . ?
C2 C3 C4 O3 -126.97(13) . . . . ?
C2 C3 C4 C5 -7.66(18) . . . . ?
C2 C3 C4 C7 119.92(14) . . . . ?
O3 C4 C5 C6 126.64(13) . . . . ?
C3 C4 C5 C6 6.14(18) . . . . ?
C7 C4 C5 C6 -120.24(14) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
O1 C1 C6 C5 175.61(13) . . . . ?
C2 C1 C6 C5 -5.25(19) . . . . ?
O3 C4 C7 C8 0.97(14) . . . . ?
C3 C4 C7 C8 117.56(12) . . . . ?
C5 C4 C7 C8 -114.23(12) . . . . ?
O3 C4 C7 C10 -175.43(10) . . . . ?
C3 C4 C7 C10 -58.84(15) . . . . ?
C5 C4 C7 C10 69.36(15) . . . . ?
C10 C7 C8 C16 -7.7(2) . . . . ?
C4 C7 C8 C16 176.44(12) . . . . ?
C10 C7 C8 C9 176.05(12) . . . . ?
C4 C7 C8 C9 0.19(14) . . . . ?
C4 O3 C9 O2 -177.13(12) . . . . ?
C4 O3 C9 C8 2.05(13) . . . . ?
C7 C8 C9 O2 177.68(14) . . . . ?
C16 C8 C9 O2 1.1(2) . . . . ?
C7 C8 C9 O3 -1.39(14) . . . . ?
C16 C8 C9 O3 -178.02(11) . . . . ?
C8 C7 C10 C11 119.84(16) . . . . ?
C4 C7 C10 C11 -64.64(16) . . . . ?
C8 C7 C10 C15 -61.31(19) . . . . ?
C4 C7 C10 C15 114.21(14) . . . . ?
C15 C10 C11 C12 -0.20(19) . . . . ?
C7 C10 C11 C12 178.65(12) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 0.4(2) . . . . ?
C11 C10 C15 C14 0.04(19) . . . . ?
C7 C10 C15 C14 -178.82(12) . . . . ?
C7 C8 C16 C21 161.92(13) . . . . ?
C9 C8 C16 C21 -22.28(18) . . . . ?
C7 C8 C16 C17 -20.8(2) . . . . ?
C9 C8 C16 C17 154.99(12) . . . . ?
C21 C16 C17 C18 0.70(19) . . . . ?
C8 C16 C17 C18 -176.63(12) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 -1.1(2) . . . . ?
C17 C18 C19 C22 178.48(12) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C22 C19 C20 C21 -178.86(13) . . . . ?
C19 C20 C21 C16 0.4(2) . . . . ?
C17 C16 C21 C20 -1.1(2) . . . . ?
C8 C16 C21 C20 176.22(12) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHLOROFORM'
####################################################################### 
# 
# 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_AB
_database_code_depnum_ccdc_archive 'CCDC 1546726'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 N O5'
_chemical_formula_sum            'C21 H13 N O5'
_chemical_formula_weight         359.32

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.4218(3)
_cell_length_b                   19.7062(6)
_cell_length_c                   10.0798(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0530(10)
_cell_angle_gamma                90
_cell_volume                     1670.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      30.51

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22846
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.633
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2879
_reflns_number_gt                2737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+1.1174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.77510(13) 1.02749(5) 0.45660(12) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.58216(12) 0.70809(5) 0.09604(9) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.64774(11) 0.80558(5) 0.19749(9) 0.0218(2) Uani 1 1 d . . . . .
O4 O 0.17238(15) 0.46463(6) 0.53675(13) 0.0409(3) Uani 1 1 d . . . . .
O5 O 0.28890(13) 0.41973(5) 0.37287(12) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.73658(17) 0.97103(7) 0.41521(14) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.57685(17) 0.95779(7) 0.35386(14) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.5039 0.9943 0.3420 0.028 Uiso 1 1 calc R U . . .
C3 C 0.53233(16) 0.89592(7) 0.31465(13) 0.0210(3) Uani 1 1 d . . . . .
H3 H 0.4280 0.8898 0.2760 0.025 Uiso 1 1 calc R U . . .
C4 C 0.64020(16) 0.83527(7) 0.32895(12) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.80568(16) 0.85218(7) 0.38124(13) 0.0195(3) Uani 1 1 d . . . . .
H5A H 0.8834 0.8172 0.3847 0.023 Uiso 1 1 calc R U . . .
C6 C 0.84857(16) 0.91366(7) 0.42289(13) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.9540 0.9208 0.4585 0.026 Uiso 1 1 calc R U . . .
C7 C 0.57187(14) 0.77804(6) 0.41098(12) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.54511(15) 0.72327(6) 0.33325(12) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.59053(15) 0.74063(7) 0.19696(13) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.55627(15) 0.78720(6) 0.55512(12) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.46099(16) 0.83866(7) 0.60341(13) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.4040 0.8681 0.5433 0.024 Uiso 1 1 calc R U . . .
C12 C 0.44975(17) 0.84675(7) 0.73965(14) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.3854 0.8819 0.7725 0.028 Uiso 1 1 calc R U . . .
C13 C 0.53151(17) 0.80398(7) 0.82735(13) 0.0237(3) Uani 1 1 d . . . . .
H13 H 0.5232 0.8097 0.9203 0.028 Uiso 1 1 calc R U . . .
C14 C 0.62635(16) 0.75237(7) 0.77971(13) 0.0227(3) Uani 1 1 d . . . . .
H14 H 0.6823 0.7229 0.8403 0.027 Uiso 1 1 calc R U . . .
C15 C 0.63904(16) 0.74409(7) 0.64453(13) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.7042 0.7090 0.6123 0.023 Uiso 1 1 calc R U . . .
C16 C 0.47538(15) 0.65668(6) 0.36401(12) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.37585(15) 0.64972(7) 0.46967(13) 0.0187(3) Uani 1 1 d . . . . .
H17 H 0.3557 0.6879 0.5238 0.022 Uiso 1 1 calc R U . . .
C18 C 0.30598(16) 0.58796(7) 0.49684(13) 0.0196(3) Uani 1 1 d . . . . .
H18 H 0.2395 0.5833 0.5695 0.024 Uiso 1 1 calc R U . . .
C19 C 0.33523(16) 0.53352(7) 0.41608(14) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.25967(14) 0.46805(6) 0.44441(13) 0.0271(3) Uani 1 1 d . . . . .
C20 C 0.43269(17) 0.53813(7) 0.31031(14) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.4511 0.4997 0.2564 0.029 Uiso 1 1 calc R U . . .
C21 C 0.50300(16) 0.60000(7) 0.28467(13) 0.0218(3) Uani 1 1 d . . . . .
H21 H 0.5706 0.6040 0.2126 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2258(17) . ?
O2 C9 1.2013(16) . ?
O3 C9 1.3676(16) . ?
O3 C4 1.4530(15) . ?
O4 N1 1.2183(17) . ?
O5 N1 1.2273(16) . ?
C1 C2 1.474(2) . ?
C1 C6 1.4716(19) . ?
C2 C3 1.329(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.5035(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.5009(19) . ?
C4 C7 1.5290(17) . ?
C5 C6 1.3261(19) . ?
C5 H5A 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3455(18) . ?
C7 C10 1.4768(17) . ?
C8 C16 1.4773(18) . ?
C8 C9 1.4854(18) . ?
C10 C11 1.3968(18) . ?
C10 C15 1.3974(18) . ?
C11 C12 1.3907(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3821(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3968(18) . ?
C16 C21 1.4004(18) . ?
C17 C18 1.3856(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3767(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 N1 1.4732(17) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21 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
C9 O3 C4 110.36(9) . . ?
O1 C1 C2 121.51(13) . . ?
O1 C1 C6 121.47(13) . . ?
C2 C1 C6 117.01(12) . . ?
C3 C2 C1 121.59(12) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 122.75(12) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
O3 C4 C5 108.95(10) . . ?
O3 C4 C3 106.75(10) . . ?
C5 C4 C3 113.72(11) . . ?
O3 C4 C7 103.42(10) . . ?
C5 C4 C7 110.06(10) . . ?
C3 C4 C7 113.29(11) . . ?
C6 C5 C4 123.10(12) . . ?
C6 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
C5 C6 C1 121.48(13) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C8 C7 C10 130.54(12) . . ?
C8 C7 C4 109.45(11) . . ?
C10 C7 C4 119.84(11) . . ?
C7 C8 C16 130.27(12) . . ?
C7 C8 C9 108.09(11) . . ?
C16 C8 C9 121.56(11) . . ?
O2 C9 O3 120.50(12) . . ?
O2 C9 C8 130.83(12) . . ?
O3 C9 C8 108.66(11) . . ?
C11 C10 C15 119.52(12) . . ?
C11 C10 C7 120.96(11) . . ?
C15 C10 C7 119.52(11) . . ?
C12 C11 C10 119.86(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.33(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.05(12) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.10(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.13(13) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C17 C16 C21 118.80(12) . . ?
C17 C16 C8 120.57(11) . . ?
C21 C16 C8 120.58(12) . . ?
C18 C17 C16 121.02(12) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 118.45(12) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 122.48(12) . . ?
C18 C19 N1 118.36(12) . . ?
C20 C19 N1 119.16(12) . . ?
O4 N1 O5 123.64(13) . . ?
O4 N1 C19 118.75(12) . . ?
O5 N1 C19 117.61(13) . . ?
C19 C20 C21 118.60(12) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C16 120.64(12) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

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 C1 C2 C3 -176.75(14) . . . . ?
C6 C1 C2 C3 4.1(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C9 O3 C4 C5 118.01(11) . . . . ?
C9 O3 C4 C3 -118.79(11) . . . . ?
C9 O3 C4 C7 0.96(13) . . . . ?
C2 C3 C4 O3 -124.76(13) . . . . ?
C2 C3 C4 C5 -4.57(18) . . . . ?
C2 C3 C4 C7 122.07(14) . . . . ?
O3 C4 C5 C6 125.03(13) . . . . ?
C3 C4 C5 C6 6.10(18) . . . . ?
C7 C4 C5 C6 -122.22(14) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
O1 C1 C6 C5 178.24(14) . . . . ?
C2 C1 C6 C5 -2.58(19) . . . . ?
O3 C4 C7 C8 0.01(13) . . . . ?
C5 C4 C7 C8 -116.26(12) . . . . ?
C3 C4 C7 C8 115.18(12) . . . . ?
O3 C4 C7 C10 175.76(10) . . . . ?
C5 C4 C7 C10 59.49(15) . . . . ?
C3 C4 C7 C10 -69.08(15) . . . . ?
C10 C7 C8 C16 7.3(2) . . . . ?
C4 C7 C8 C16 -177.56(12) . . . . ?
C10 C7 C8 C9 -176.03(12) . . . . ?
C4 C7 C8 C9 -0.89(14) . . . . ?
C4 O3 C9 O2 177.65(12) . . . . ?
C4 O3 C9 C8 -1.52(14) . . . . ?
C7 C8 C9 O2 -177.54(14) . . . . ?
C16 C8 C9 O2 -0.5(2) . . . . ?
C7 C8 C9 O3 1.52(14) . . . . ?
C16 C8 C9 O3 178.54(11) . . . . ?
C8 C7 C10 C11 -124.53(15) . . . . ?
C4 C7 C10 C11 60.75(17) . . . . ?
C8 C7 C10 C15 55.99(19) . . . . ?
C4 C7 C10 C15 -118.73(13) . . . . ?
C15 C10 C11 C12 0.25(19) . . . . ?
C7 C10 C11 C12 -179.23(12) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C11 C10 C15 C14 0.08(19) . . . . ?
C7 C10 C15 C14 179.58(12) . . . . ?
C7 C8 C16 C17 22.9(2) . . . . ?
C9 C8 C16 C17 -153.43(12) . . . . ?
C7 C8 C16 C21 -159.59(13) . . . . ?
C9 C8 C16 C21 24.12(18) . . . . ?
C21 C16 C17 C18 0.42(19) . . . . ?
C8 C16 C17 C18 178.01(12) . . . . ?
C16 C17 C18 C19 -0.82(19) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C17 C18 C19 N1 -179.46(11) . . . . ?
C18 C19 N1 O4 1.08(18) . . . . ?
C20 C19 N1 O4 -179.09(13) . . . . ?
C18 C19 N1 O5 -178.85(12) . . . . ?
C20 C19 N1 O5 0.98(18) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
N1 C19 C20 C21 179.97(12) . . . . ?
C19 C20 C21 C16 -0.2(2) . . . . ?
C17 C16 C21 C20 0.11(19) . . . . ?
C8 C16 C21 C20 -177.48(12) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHLOROFORM'
####################################################################### 
# 
# 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_mo_ABMET_0m
_database_code_depnum_ccdc_archive 'CCDC 1546724'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   13.0187(3)
_cell_length_b                   6.55490(10)
_cell_length_c                   20.3272(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.3930(10)
_cell_angle_gamma                90
_cell_volume                     1687.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      36.24

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21239
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2928
_reflns_number_gt                2743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.8591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.97766(8) 0.29562(17) 0.44868(6) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.43322(7) 0.19812(14) 0.47697(4) 0.0179(2) Uani 1 1 d . . . . .
O3 O 0.60016(7) 0.24603(14) 0.47032(4) 0.0167(2) Uani 1 1 d . . . . .
C1 C 0.89710(10) 0.2997(2) 0.47008(7) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.82928(10) 0.4820(2) 0.46232(7) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.8502 0.6007 0.4419 0.025 Uiso 1 1 calc R U . . .
C3 C 0.73973(10) 0.4853(2) 0.48304(6) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.6990 0.6070 0.4773 0.021 Uiso 1 1 calc R U . . .
C4 C 0.70033(10) 0.3041(2) 0.51511(6) 0.0168(3) Uani 1 1 d . . . . .
C5 C 0.77132(10) 0.1203(2) 0.52195(7) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.7505 -0.0006 0.5411 0.024 Uiso 1 1 calc R U . . .
C6 C 0.86171(10) 0.1199(2) 0.50234(7) 0.0230(3) Uani 1 1 d . . . . .
H6 H 0.9046 0.0009 0.5092 0.028 Uiso 1 1 calc R U . . .
C7 C 0.67033(10) 0.34810(19) 0.58216(6) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.56753(10) 0.30592(19) 0.57557(6) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.52264(9) 0.24283(18) 0.50495(6) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.74855(10) 0.4120(2) 0.64354(6) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.81452(13) 0.5795(2) 0.64381(8) 0.0321(4) Uani 1 1 d . . . . .
H11 H 0.8130 0.6509 0.6029 0.038 Uiso 1 1 calc R U . . .
C12 C 0.88232(14) 0.6425(3) 0.70340(8) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.9255 0.7590 0.7028 0.044 Uiso 1 1 calc R U . . .
C13 C 0.88872(11) 0.5398(2) 0.76401(7) 0.0263(3) Uani 1 1 d . . . . .
C14 C 0.95990(13) 0.6158(3) 0.82876(8) 0.0359(4) Uani 1 1 d . . . . .
H14A H 0.9284 0.7368 0.8445 0.054 Uiso 1 1 calc R U . . .
H14B H 1.0290 0.6512 0.8206 0.054 Uiso 1 1 calc R U . . .
H14C H 0.9685 0.5087 0.8633 0.054 Uiso 1 1 calc R U . . .
C15 C 0.82631(11) 0.3678(2) 0.76276(7) 0.0252(3) Uani 1 1 d . . . . .
H15 H 0.8314 0.2910 0.8030 0.030 Uiso 1 1 calc R U . . .
C16 C 0.75647(11) 0.3057(2) 0.70369(7) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.7135 0.1889 0.7044 0.027 Uiso 1 1 calc R U . . .
C17 C 0.49901(10) 0.3243(2) 0.62396(6) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.49870(10) 0.5012(2) 0.66205(7) 0.0196(3) Uani 1 1 d . . . . .
H18 H 0.5468 0.6084 0.6596 0.024 Uiso 1 1 calc R U . . .
C19 C 0.42833(11) 0.5212(2) 0.70350(7) 0.0234(3) Uani 1 1 d . . . . .
H19 H 0.4282 0.6423 0.7292 0.028 Uiso 1 1 calc R U . . .
C20 C 0.35821(11) 0.3650(2) 0.70756(7) 0.0248(3) Uani 1 1 d . . . . .
H20 H 0.3097 0.3795 0.7357 0.030 Uiso 1 1 calc R U . . .
C21 C 0.35897(11) 0.1877(2) 0.67046(7) 0.0237(3) Uani 1 1 d . . . . .
H21 H 0.3115 0.0801 0.6737 0.028 Uiso 1 1 calc R U . . .
C22 C 0.42876(10) 0.1669(2) 0.62873(6) 0.0198(3) Uani 1 1 d . . . . .
H22 H 0.4288 0.0453 0.6033 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2251(17) . ?
O2 C9 1.2074(15) . ?
O3 C9 1.3578(15) . ?
O3 C4 1.4574(15) . ?
C1 C6 1.474(2) . ?
C1 C2 1.473(2) . ?
C2 C3 1.3283(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.5013(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.5050(18) . ?
C4 C7 1.5297(18) . ?
C5 C6 1.327(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3425(18) . ?
C7 C10 1.4767(18) . ?
C8 C17 1.4779(18) . ?
C8 C9 1.4781(18) . ?
C10 C11 1.393(2) . ?
C10 C16 1.3905(19) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C15 1.386(2) . ?
C13 C14 1.508(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3967(19) . ?
C17 C18 1.3951(19) . ?
C18 C19 1.3871(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(2) . ?
C21 H21 0.9500 . ?
C22 H22 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
C9 O3 C4 110.19(9) . . ?
O1 C1 C6 121.47(13) . . ?
O1 C1 C2 121.40(13) . . ?
C6 C1 C2 117.09(12) . . ?
C3 C2 C1 121.83(13) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 122.58(12) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
O3 C4 C3 106.35(10) . . ?
O3 C4 C5 106.87(10) . . ?
C3 C4 C5 114.15(11) . . ?
O3 C4 C7 103.28(10) . . ?
C3 C4 C7 114.90(11) . . ?
C5 C4 C7 110.29(10) . . ?
C6 C5 C4 122.84(13) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 121.49(13) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C8 C7 C10 128.25(12) . . ?
C8 C7 C4 109.06(11) . . ?
C10 C7 C4 122.54(11) . . ?
C7 C8 C17 131.17(12) . . ?
C7 C8 C9 108.37(11) . . ?
C17 C8 C9 120.36(11) . . ?
O2 C9 O3 120.73(11) . . ?
O2 C9 C8 130.28(12) . . ?
O3 C9 C8 108.97(10) . . ?
C11 C10 C16 118.13(12) . . ?
C11 C10 C7 122.07(12) . . ?
C16 C10 C7 119.79(12) . . ?
C12 C11 C10 120.38(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.70(15) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C15 C13 C12 117.60(13) . . ?
C15 C13 C14 121.58(14) . . ?
C12 C13 C14 120.81(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.19(13) . . ?
C13 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C10 120.91(13) . . ?
C15 C16 H16 119.5 . . ?
C10 C16 H16 119.5 . . ?
C22 C17 C18 119.29(12) . . ?
C22 C17 C8 119.47(12) . . ?
C18 C17 C8 121.13(12) . . ?
C19 C18 C17 120.20(13) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.19(13) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 119.91(13) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.22(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.18(13) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?

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 C1 C2 C3 177.38(13) . . . . ?
C6 C1 C2 C3 -0.34(19) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C9 O3 C4 C3 -124.49(11) . . . . ?
C9 O3 C4 C5 113.20(11) . . . . ?
C9 O3 C4 C7 -3.16(12) . . . . ?
C2 C3 C4 O3 -117.25(13) . . . . ?
C2 C3 C4 C5 0.33(18) . . . . ?
C2 C3 C4 C7 129.16(13) . . . . ?
O3 C4 C5 C6 118.34(13) . . . . ?
C3 C4 C5 C6 1.07(18) . . . . ?
C7 C4 C5 C6 -130.06(13) . . . . ?
C4 C5 C6 C1 -2.1(2) . . . . ?
O1 C1 C6 C5 -176.00(13) . . . . ?
C2 C1 C6 C5 1.72(19) . . . . ?
O3 C4 C7 C8 3.59(13) . . . . ?
C3 C4 C7 C8 118.96(12) . . . . ?
C5 C4 C7 C8 -110.31(12) . . . . ?
O3 C4 C7 C10 179.56(11) . . . . ?
C3 C4 C7 C10 -65.07(16) . . . . ?
C5 C4 C7 C10 65.65(15) . . . . ?
C10 C7 C8 C17 5.4(2) . . . . ?
C4 C7 C8 C17 -178.93(12) . . . . ?
C10 C7 C8 C9 -178.36(12) . . . . ?
C4 C7 C8 C9 -2.69(14) . . . . ?
C4 O3 C9 O2 -179.95(11) . . . . ?
C4 O3 C9 C8 1.73(13) . . . . ?
C7 C8 C9 O2 -177.42(13) . . . . ?
C17 C8 C9 O2 -0.7(2) . . . . ?
C7 C8 C9 O3 0.69(14) . . . . ?
C17 C8 C9 O3 177.42(10) . . . . ?
C8 C7 C10 C11 -130.64(16) . . . . ?
C4 C7 C10 C11 54.21(19) . . . . ?
C8 C7 C10 C16 48.2(2) . . . . ?
C4 C7 C10 C16 -126.91(14) . . . . ?
C16 C10 C11 C12 -3.0(2) . . . . ?
C7 C10 C11 C12 175.94(15) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C11 C12 C13 C15 1.4(3) . . . . ?
C11 C12 C13 C14 -177.60(16) . . . . ?
C12 C13 C15 C16 -2.8(2) . . . . ?
C14 C13 C15 C16 176.21(14) . . . . ?
C13 C15 C16 C10 1.3(2) . . . . ?
C11 C10 C16 C15 1.6(2) . . . . ?
C7 C10 C16 C15 -177.32(12) . . . . ?
C7 C8 C17 C22 -136.44(14) . . . . ?
C9 C8 C17 C22 47.69(17) . . . . ?
C7 C8 C17 C18 47.4(2) . . . . ?
C9 C8 C17 C18 -128.43(13) . . . . ?
C22 C17 C18 C19 -0.83(19) . . . . ?
C8 C17 C18 C19 175.30(12) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 C17 0.2(2) . . . . ?
C18 C17 C22 C21 0.57(19) . . . . ?
C8 C17 C22 C21 -175.62(12) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHLOROFORM'
