# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1814953'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-04-16 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         ' C20 H14 N2 O5'
_chemical_formula_sum            ' C20 H14 N2 O5'
_chemical_formula_weight         362.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.6428(3)
_cell_length_b                   14.2542(6)
_cell_length_c                   17.8105(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1686.44(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      66.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.871
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19936
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.972
_diffrn_reflns_theta_max         66.760
_diffrn_reflns_theta_full        66.760
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2973
_reflns_number_gt                2898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.1459P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0071(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.08(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2973
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C1 C 0.3551(2) 1.01367(11) 0.62586(9) 0.0339(4) Uani 1 1 d . . . . .
H1 H 0.4064 1.0647 0.6573 0.041 Uiso 1 1 calc R U . . .
C2 C 0.0794(3) 1.18855(11) 0.40369(9) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.2779(3) 1.16563(12) 0.38650(9) 0.0375(4) Uani 1 1 d . . . . .
H3 H 0.3361 1.1857 0.3418 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3862(3) 1.11274(12) 0.43688(9) 0.0374(4) Uani 1 1 d . . . . .
H4 H 0.5191 1.0969 0.4265 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2969(2) 1.08294(11) 0.50340(9) 0.0313(3) Uani 1 1 d . . . . .
C6 C 0.0969(2) 1.10598(10) 0.52012(8) 0.0288(3) Uani 1 1 d . . . . .
C7 C -0.0123(3) 1.16020(10) 0.46927(8) 0.0302(3) Uani 1 1 d . . . . .
H7 H -0.1448 1.1770 0.4794 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0006(2) 1.07338(10) 0.58976(9) 0.0289(3) Uani 1 1 d . . . . .
C9 C 0.1263(2) 1.00340(11) 0.63609(8) 0.0302(3) Uani 1 1 d . . . . .
C10 C 0.0907(2) 0.89513(11) 0.61425(9) 0.0311(3) Uani 1 1 d . . . . .
C11 C 0.3009(3) 0.85387(12) 0.63222(11) 0.0414(4) Uani 1 1 d . . . . .
H11A H 0.2922 0.8126 0.6754 0.050 Uiso 1 1 calc R U . . .
H11B H 0.3493 0.8176 0.5898 0.050 Uiso 1 1 calc R U . . .
C12 C 0.0792(3) 1.01817(11) 0.71607(9) 0.0356(4) Uani 1 1 d . . . . .
C13 C -0.0728(3) 0.85337(12) 0.66358(9) 0.0371(4) Uani 1 1 d . . . . .
H13 H -0.1900 0.8883 0.6696 0.045 Uiso 1 1 calc R U . . .
C14 C -0.0634(3) 0.77226(14) 0.69861(10) 0.0480(5) Uani 1 1 d . . . . .
H14A H 0.0510 0.7351 0.6942 0.058 Uiso 1 1 calc R U . . .
H14B H -0.1712 0.7521 0.7278 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0275(2) 0.88790(10) 0.53129(9) 0.0305(3) Uani 1 1 d . . . . .
C16 C -0.1733(3) 0.90297(12) 0.51130(9) 0.0349(4) Uani 1 1 d . . . . .
H16 H -0.2690 0.9107 0.5489 0.042 Uiso 1 1 calc R U . . .
C17 C -0.2335(3) 0.90671(13) 0.43686(10) 0.0428(4) Uani 1 1 d . . . . .
H17 H -0.3680 0.9173 0.4252 0.051 Uiso 1 1 calc R U . . .
C18 C -0.0948(3) 0.89477(13) 0.37999(10) 0.0477(5) Uani 1 1 d . . . . .
H18 H -0.1341 0.8986 0.3300 0.057 Uiso 1 1 calc R U . . .
C19 C 0.1024(4) 0.87707(14) 0.39858(11) 0.0523(5) Uani 1 1 d . . . . .
H19 H 0.1962 0.8678 0.3606 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1644(3) 0.87279(13) 0.47311(10) 0.0421(4) Uani 1 1 d . . . . .
H20 H 0.2983 0.8598 0.4843 0.051 Uiso 1 1 calc R U . . .
N1 N 0.0426(3) 1.02978(12) 0.77795(9) 0.0488(4) Uani 1 1 d . . . . .
N2 N -0.0369(2) 1.24485(10) 0.35054(7) 0.0376(3) Uani 1 1 d . . . . .
O1 O 0.0451(2) 1.27058(10) 0.29244(7) 0.0502(4) Uani 1 1 d . . . . .
O2 O -0.2120(2) 1.26474(9) 0.36687(7) 0.0453(3) Uani 1 1 d . . . . .
O3 O 0.41157(16) 1.02848(8) 0.54868(7) 0.0368(3) Uani 1 1 d . . . . .
O4 O -0.16465(17) 1.09794(8) 0.61028(6) 0.0366(3) Uani 1 1 d . . . . .
O5 O 0.43755(17) 0.92962(8) 0.64775(7) 0.0409(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O5 1.374(2) . ?
C1 O3 1.440(2) . ?
C1 C9 1.538(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.378(2) . ?
C2 C3 1.393(2) . ?
C2 N2 1.462(2) . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9300 . ?
C5 O3 1.3540(19) . ?
C5 C6 1.401(2) . ?
C6 C7 1.394(2) . ?
C6 C8 1.471(2) . ?
C7 H7 0.9300 . ?
C8 O4 1.2086(19) . ?
C8 C9 1.541(2) . ?
C9 C12 1.474(2) . ?
C9 C10 1.609(2) . ?
C10 C13 1.519(2) . ?
C10 C15 1.539(2) . ?
C10 C11 1.548(2) . ?
C11 O5 1.438(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.141(2) . ?
C13 C14 1.315(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C20 1.395(2) . ?
C15 C16 1.397(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N2 O1 1.2255(19) . ?
N2 O2 1.232(2) . ?

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
O5 C1 O3 107.14(14) . . ?
O5 C1 C9 106.10(13) . . ?
O3 C1 C9 112.60(13) . . ?
O5 C1 H1 110.3 . . ?
O3 C1 H1 110.3 . . ?
C9 C1 H1 110.3 . . ?
C7 C2 C3 122.41(15) . . ?
C7 C2 N2 118.46(15) . . ?
C3 C2 N2 119.13(15) . . ?
C4 C3 C2 118.72(15) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.00(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
O3 C5 C4 116.25(14) . . ?
O3 C5 C6 122.80(15) . . ?
C4 C5 C6 120.92(15) . . ?
C7 C6 C5 119.03(14) . . ?
C7 C6 C8 119.79(14) . . ?
C5 C6 C8 121.17(14) . . ?
C2 C7 C6 118.92(15) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
O4 C8 C6 123.94(14) . . ?
O4 C8 C9 121.20(14) . . ?
C6 C8 C9 114.86(13) . . ?
C12 C9 C1 108.12(14) . . ?
C12 C9 C8 108.05(13) . . ?
C1 C9 C8 114.25(13) . . ?
C12 C9 C10 109.85(12) . . ?
C1 C9 C10 102.01(12) . . ?
C8 C9 C10 114.31(12) . . ?
C13 C10 C15 109.51(13) . . ?
C13 C10 C11 112.12(13) . . ?
C15 C10 C11 114.76(14) . . ?
C13 C10 C9 109.95(13) . . ?
C15 C10 C9 109.65(12) . . ?
C11 C10 C9 100.47(12) . . ?
O5 C11 C10 108.90(13) . . ?
O5 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
O5 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N1 C12 C9 179.87(19) . . ?
C14 C13 C10 125.81(18) . . ?
C14 C13 H13 117.1 . . ?
C10 C13 H13 117.1 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C20 C15 C16 117.19(16) . . ?
C20 C15 C10 123.04(15) . . ?
C16 C15 C10 119.64(14) . . ?
C17 C16 C15 121.67(16) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.33(18) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 118.82(17) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.34(17) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 120.57(18) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
O1 N2 O2 123.37(15) . . ?
O1 N2 C2 118.44(15) . . ?
O2 N2 C2 118.19(14) . . ?
C5 O3 C1 120.39(13) . . ?
C1 O5 C11 110.42(12) . . ?

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
C7 C2 C3 C4 0.0(2) . . . . ?
N2 C2 C3 C4 179.92(15) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 O3 177.79(15) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
O3 C5 C6 C7 -178.13(14) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
O3 C5 C6 C8 1.4(2) . . . . ?
C4 C5 C6 C8 178.98(15) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
N2 C2 C7 C6 179.59(14) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C8 C6 C7 C2 -178.78(13) . . . . ?
C7 C6 C8 O4 -7.4(2) . . . . ?
C5 C6 C8 O4 173.05(15) . . . . ?
C7 C6 C8 C9 172.16(13) . . . . ?
C5 C6 C8 C9 -7.4(2) . . . . ?
O5 C1 C9 C12 80.48(16) . . . . ?
O3 C1 C9 C12 -162.63(13) . . . . ?
O5 C1 C9 C8 -159.19(13) . . . . ?
O3 C1 C9 C8 -42.29(18) . . . . ?
O5 C1 C9 C10 -35.30(16) . . . . ?
O3 C1 C9 C10 81.60(15) . . . . ?
O4 C8 C9 C12 -32.3(2) . . . . ?
C6 C8 C9 C12 148.08(14) . . . . ?
O4 C8 C9 C1 -152.70(15) . . . . ?
C6 C8 C9 C1 27.70(19) . . . . ?
O4 C8 C9 C10 90.31(17) . . . . ?
C6 C8 C9 C10 -89.30(16) . . . . ?
C12 C9 C10 C13 29.28(17) . . . . ?
C1 C9 C10 C13 143.79(14) . . . . ?
C8 C9 C10 C13 -92.36(16) . . . . ?
C12 C9 C10 C15 149.74(13) . . . . ?
C1 C9 C10 C15 -95.75(14) . . . . ?
C8 C9 C10 C15 28.10(17) . . . . ?
C12 C9 C10 C11 -89.04(15) . . . . ?
C1 C9 C10 C11 25.47(15) . . . . ?
C8 C9 C10 C11 149.32(14) . . . . ?
C13 C10 C11 O5 -125.82(14) . . . . ?
C15 C10 C11 O5 108.42(17) . . . . ?
C9 C10 C11 O5 -9.09(17) . . . . ?
C15 C10 C13 C14 106.26(19) . . . . ?
C11 C10 C13 C14 -22.3(2) . . . . ?
C9 C10 C13 C14 -133.20(17) . . . . ?
C13 C10 C15 C20 -145.76(16) . . . . ?
C11 C10 C15 C20 -18.7(2) . . . . ?
C9 C10 C15 C20 93.51(17) . . . . ?
C13 C10 C15 C16 38.57(19) . . . . ?
C11 C10 C15 C16 165.68(14) . . . . ?
C9 C10 C15 C16 -82.15(17) . . . . ?
C20 C15 C16 C17 -2.6(2) . . . . ?
C10 C15 C16 C17 173.30(15) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C15 -1.0(3) . . . . ?
C16 C15 C20 C19 2.8(2) . . . . ?
C10 C15 C20 C19 -172.93(16) . . . . ?
C7 C2 N2 O1 179.53(14) . . . . ?
C3 C2 N2 O1 -0.4(2) . . . . ?
C7 C2 N2 O2 0.2(2) . . . . ?
C3 C2 N2 O2 -179.71(15) . . . . ?
C4 C5 O3 C1 164.24(14) . . . . ?
C6 C5 O3 C1 -18.1(2) . . . . ?
O5 C1 O3 C5 154.53(13) . . . . ?
C9 C1 O3 C5 38.25(19) . . . . ?
O3 C1 O5 C11 -89.23(16) . . . . ?
C9 C1 O5 C11 31.27(18) . . . . ?
C10 C11 O5 C1 -13.5(2) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1814954'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-04-16 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         'C20 H14 N2 O5'
_chemical_formula_sum            'C20 H14 N2 O5'
_chemical_formula_weight         362.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   11.4782(3)
_cell_length_b                   14.6774(4)
_cell_length_c                   10.8540(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.8240(10)
_cell_angle_gamma                90
_cell_volume                     1645.97(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      4.28
_cell_measurement_theta_max      66.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.893
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16118
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.235
_diffrn_reflns_theta_max         66.689
_diffrn_reflns_theta_full        66.689
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2888
_reflns_number_gt                2625
_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)+(0.0469P)²+0.4756P] 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         2888
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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
C1 C 0.37306(11) 0.97036(8) 0.13051(11) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.48486(12) 1.01375(8) 0.25600(12) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.5512 1.0382 0.2312 0.033 Uiso 1 1 calc R U . . .
C3 C 0.35874(12) 1.14856(8) 0.23065(12) 0.0278(3) Uani 1 1 d . . . . .
C4 C 0.35361(13) 1.23206(9) 0.28914(13) 0.0336(3) Uani 1 1 d . . . . .
H4 H 0.3997 1.2407 0.3830 0.040 Uiso 1 1 calc R U . . .
C5 C 0.28023(13) 1.30157(9) 0.20756(14) 0.0341(3) Uani 1 1 d . . . . .
H5 H 0.2762 1.3576 0.2456 0.041 Uiso 1 1 calc R U . . .
C6 C 0.21206(12) 1.28727(8) 0.06736(13) 0.0305(3) Uani 1 1 d . . . . .
C7 C 0.21015(11) 1.20398(8) 0.00821(12) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.1609 1.1953 -0.0852 0.033 Uiso 1 1 calc R U . . .
C8 C 0.28343(11) 1.13276(8) 0.09095(12) 0.0251(3) Uani 1 1 d . . . . .
C9 C 0.28415(11) 1.04325(8) 0.03050(11) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.42975(11) 0.91750(8) 0.05478(11) 0.0246(3) Uani 1 1 d . . . . .
C11 C 0.31090(11) 0.90434(8) 0.20314(11) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.43345(12) 0.88334(9) 0.33844(12) 0.0316(3) Uani 1 1 d . . . . .
H12A H 0.4134 0.8900 0.4160 0.038 Uiso 1 1 calc R U . . .
H12B H 0.4614 0.8211 0.3370 0.038 Uiso 1 1 calc R U . . .
C13 C 0.21219(12) 0.95744(8) 0.23394(12) 0.0286(3) Uani 1 1 d . . . . .
H13 H 0.2448 0.9964 0.3090 0.034 Uiso 1 1 calc R U . . .
C14 C 0.08639(13) 0.95344(9) 0.16500(14) 0.0369(3) Uani 1 1 d . . . . .
H14A H 0.0492 0.9155 0.0891 0.044 Uiso 1 1 calc R U . . .
H14B H 0.0340 0.9886 0.1918 0.044 Uiso 1 1 calc R U . . .
C15 C 0.25026(11) 0.81737(8) 0.12387(12) 0.0250(3) Uani 1 1 d . . . . .
C16 C 0.25853(12) 0.73698(8) 0.19592(13) 0.0302(3) Uani 1 1 d . . . . .
H16 H 0.3051 0.7365 0.2907 0.036 Uiso 1 1 calc R U . . .
C17 C 0.19845(13) 0.65775(8) 0.12853(14) 0.0339(3) Uani 1 1 d . . . . .
H17 H 0.2050 0.6049 0.1783 0.041 Uiso 1 1 calc R U . . .
C18 C 0.12891(13) 0.65705(9) -0.01240(14) 0.0344(3) Uani 1 1 d . . . . .
H18 H 0.0898 0.6037 -0.0578 0.041 Uiso 1 1 calc R U . . .
C19 C 0.11812(13) 0.73662(9) -0.08513(13) 0.0336(3) Uani 1 1 d . . . . .
H19 H 0.0706 0.7368 -0.1798 0.040 Uiso 1 1 calc R U . . .
C20 C 0.17771(12) 0.81637(8) -0.01790(12) 0.0291(3) Uani 1 1 d . . . . .
H20 H 0.1691 0.8695 -0.0679 0.035 Uiso 1 1 calc R U . . .
N1 N 0.47466(10) 0.87943(7) -0.00572(11) 0.0299(2) Uani 1 1 d . . . . .
N2 N 0.14350(11) 1.36434(7) -0.02056(13) 0.0369(3) Uani 1 1 d . . . . .
O1 O 0.13978(11) 1.43619(6) 0.03481(12) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.09478(11) 1.35299(7) -0.14477(11) 0.0495(3) Uani 1 1 d . . . . .
O3 O 0.43719(8) 1.08374(6) 0.31607(8) 0.0306(2) Uani 1 1 d . . . . .
O4 O 0.53480(8) 0.94558(6) 0.35132(8) 0.0315(2) Uani 1 1 d . . . . .
O5 O 0.22400(8) 1.02729(5) -0.09072(8) 0.0285(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.4720(16) . ?
C1 C2 1.5443(16) . ?
C1 C9 1.5490(15) . ?
C1 C11 1.5998(15) . ?
C2 O4 1.3725(14) . ?
C2 O3 1.4459(15) . ?
C2 H2 0.9800 . ?
C3 O3 1.3594(15) . ?
C3 C4 1.3933(17) . ?
C3 C8 1.3994(17) . ?
C4 C5 1.3728(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3910(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.3765(17) . ?
C6 N2 1.4681(16) . ?
C7 C8 1.3959(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.4701(16) . ?
C9 O5 1.2130(14) . ?
C10 N1 1.1420(16) . ?
C11 C15 1.5273(16) . ?
C11 C13 1.5274(16) . ?
C11 C12 1.5590(16) . ?
C12 O4 1.4372(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.3066(19) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.3957(16) . ?
C15 C20 1.3947(17) . ?
C16 C17 1.3869(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.3833(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.3846(18) . ?
C18 H18 0.9300 . ?
C19 C20 1.3914(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N2 O1 1.2237(15) . ?
N2 O2 1.2253(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 108.07(9) . . ?
C10 C1 C9 106.81(9) . . ?
C2 C1 C9 111.96(9) . . ?
C10 C1 C11 110.88(9) . . ?
C2 C1 C11 101.11(9) . . ?
C9 C1 C11 117.68(9) . . ?
O4 C2 O3 107.09(9) . . ?
O4 C2 C1 106.14(9) . . ?
O3 C2 C1 111.01(9) . . ?
O4 C2 H2 110.8 . . ?
O3 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
O3 C3 C4 116.85(11) . . ?
O3 C3 C8 122.42(11) . . ?
C4 C3 C8 120.71(12) . . ?
C5 C4 C3 119.72(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.22(12) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 122.10(12) . . ?
C7 C6 N2 119.08(11) . . ?
C5 C6 N2 118.79(11) . . ?
C6 C7 C8 118.84(11) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C3 119.19(11) . . ?
C7 C8 C9 120.07(10) . . ?
C3 C8 C9 120.72(11) . . ?
O5 C9 C8 123.06(10) . . ?
O5 C9 C1 121.11(10) . . ?
C8 C9 C1 115.76(9) . . ?
N1 C10 C1 177.49(12) . . ?
C15 C11 C13 110.50(9) . . ?
C15 C11 C12 111.60(10) . . ?
C13 C11 C12 110.22(10) . . ?
C15 C11 C1 114.85(9) . . ?
C13 C11 C1 109.35(9) . . ?
C12 C11 C1 99.84(9) . . ?
O4 C12 C11 109.02(9) . . ?
O4 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
O4 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C11 126.29(11) . . ?
C14 C13 H13 116.9 . . ?
C11 C13 H13 116.9 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C20 118.14(11) . . ?
C16 C15 C11 119.20(10) . . ?
C20 C15 C11 122.47(10) . . ?
C17 C16 C15 121.10(12) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.28(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.30(12) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.61(12) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.55(11) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
O1 N2 O2 124.10(12) . . ?
O1 N2 C6 117.92(12) . . ?
O2 N2 C6 117.97(11) . . ?
C3 O3 C2 117.26(9) . . ?
C2 O4 C12 109.60(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
C10 C1 C2 O4 -77.95(11) . . . . ?
C9 C1 C2 O4 164.68(9) . . . . ?
C11 C1 C2 O4 38.55(11) . . . . ?
C10 C1 C2 O3 166.02(9) . . . . ?
C9 C1 C2 O3 48.65(12) . . . . ?
C11 C1 C2 O3 -77.48(10) . . . . ?
O3 C3 C4 C5 177.42(11) . . . . ?
C8 C3 C4 C5 -4.13(19) . . . . ?
C3 C4 C5 C6 0.00(19) . . . . ?
C4 C5 C6 C7 3.50(19) . . . . ?
C4 C5 C6 N2 -174.49(11) . . . . ?
C5 C6 C7 C8 -2.76(18) . . . . ?
N2 C6 C7 C8 175.23(10) . . . . ?
C6 C7 C8 C3 -1.40(17) . . . . ?
C6 C7 C8 C9 -179.51(10) . . . . ?
O3 C3 C8 C7 -176.80(11) . . . . ?
C4 C3 C8 C7 4.84(18) . . . . ?
O3 C3 C8 C9 1.29(17) . . . . ?
C4 C3 C8 C9 -177.07(11) . . . . ?
C7 C8 C9 O5 0.67(17) . . . . ?
C3 C8 C9 O5 -177.40(11) . . . . ?
C7 C8 C9 C1 177.60(10) . . . . ?
C3 C8 C9 C1 -0.48(15) . . . . ?
C10 C1 C9 O5 34.46(14) . . . . ?
C2 C1 C9 O5 152.58(11) . . . . ?
C11 C1 C9 O5 -90.92(13) . . . . ?
C10 C1 C9 C8 -142.53(10) . . . . ?
C2 C1 C9 C8 -24.41(13) . . . . ?
C11 C1 C9 C8 92.09(12) . . . . ?
C10 C1 C11 C15 -34.22(13) . . . . ?
C2 C1 C11 C15 -148.64(10) . . . . ?
C9 C1 C11 C15 89.13(12) . . . . ?
C10 C1 C11 C13 -159.10(9) . . . . ?
C2 C1 C11 C13 86.49(10) . . . . ?
C9 C1 C11 C13 -35.75(13) . . . . ?
C10 C1 C11 C12 85.26(11) . . . . ?
C2 C1 C11 C12 -29.16(11) . . . . ?
C9 C1 C11 C12 -151.39(10) . . . . ?
C15 C11 C12 O4 134.59(10) . . . . ?
C13 C11 C12 O4 -102.23(11) . . . . ?
C1 C11 C12 O4 12.75(12) . . . . ?
C15 C11 C13 C14 -24.63(17) . . . . ?
C12 C11 C13 C14 -148.45(13) . . . . ?
C1 C11 C13 C14 102.74(14) . . . . ?
C13 C11 C15 C16 -90.96(13) . . . . ?
C12 C11 C15 C16 32.06(15) . . . . ?
C1 C11 C15 C16 144.77(10) . . . . ?
C13 C11 C15 C20 83.86(13) . . . . ?
C12 C11 C15 C20 -153.12(11) . . . . ?
C1 C11 C15 C20 -40.41(15) . . . . ?
C20 C15 C16 C17 1.20(18) . . . . ?
C11 C15 C16 C17 176.24(11) . . . . ?
C15 C16 C17 C18 0.08(19) . . . . ?
C16 C17 C18 C19 -1.09(19) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 C15 0.52(19) . . . . ?
C16 C15 C20 C19 -1.50(18) . . . . ?
C11 C15 C20 C19 -176.37(11) . . . . ?
C7 C6 N2 O1 175.59(11) . . . . ?
C5 C6 N2 O1 -6.36(17) . . . . ?
C7 C6 N2 O2 -5.17(17) . . . . ?
C5 C6 N2 O2 172.89(12) . . . . ?
C4 C3 O3 C2 -155.73(11) . . . . ?
C8 C3 O3 C2 25.85(16) . . . . ?
O4 C2 O3 C3 -166.09(9) . . . . ?
C1 C2 O3 C3 -50.65(13) . . . . ?
O3 C2 O4 C12 86.67(11) . . . . ?
C1 C2 O4 C12 -31.98(12) . . . . ?
C11 C12 O4 C2 11.48(13) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1814955'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-04-16 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 H19 N O3'
_chemical_formula_sum            ' C21 H19 N O3'
_chemical_formula_weight         333.37

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'

_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'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0542(2)
_cell_length_b                   14.1154(4)
_cell_length_c                   17.6777(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1760.22(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      66.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.678
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14032
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.1253
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.906
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_full        66.588
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3094
_reflns_number_gt                2971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.5969P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0084(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3094
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4455(4) 0.54962(19) -0.01146(15) 0.0239(6) Uani 1 1 d . . . . .
C2 C 0.6556(4) 0.5272(2) -0.02042(19) 0.0360(7) Uani 1 1 d . . . . .
H2 H 0.7381 0.5735 -0.0026 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7332(7) 0.4556(4) -0.0483(4) 0.100(2) Uani 1 1 d . . . . .
H3A H 0.6593 0.4064 -0.0672 0.120 Uiso 1 1 calc R U . . .
H3B H 0.8647 0.4515 -0.0500 0.120 Uiso 1 1 calc R U . . .
C4 C 0.4014(4) 0.64185(19) -0.05615(15) 0.0270(6) Uani 1 1 d . . . . .
H4A H 0.4911 0.6497 -0.0973 0.032 Uiso 1 1 calc R U . . .
H4B H 0.2746 0.6391 -0.0773 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4961(4) 0.68524(18) 0.06532(15) 0.0247(6) Uani 1 1 d . . . . .
H5 H 0.6336 0.6793 0.0590 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4093(4) 0.58498(18) 0.07180(15) 0.0221(6) Uani 1 1 d . . . . .
C7 C 0.5106(4) 0.5319(2) 0.13016(16) 0.0291(6) Uani 1 1 d . . . . .
C8 C 0.1950(4) 0.59023(18) 0.09508(15) 0.0232(6) Uani 1 1 d . . . . .
H8 H 0.1626 0.5299 0.1192 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1625(4) 0.66761(19) 0.15286(15) 0.0236(6) Uani 1 1 d . . . . .
C10 C 0.2895(4) 0.74235(19) 0.16172(15) 0.0255(6) Uani 1 1 d . . . . .
C11 C 0.2516(5) 0.8154(2) 0.21220(17) 0.0328(7) Uani 1 1 d . . . . .
H11 H 0.3374 0.8649 0.2181 0.039 Uiso 1 1 calc R U . . .
C12 C 0.0863(5) 0.8141(2) 0.25325(17) 0.0364(7) Uani 1 1 d . . . . .
H12 H 0.0622 0.8629 0.2872 0.044 Uiso 1 1 calc R U . . .
C13 C -0.0468(5) 0.7413(2) 0.24540(16) 0.0357(7) Uani 1 1 d . . . . .
C14 C -0.0035(4) 0.6686(2) 0.19528(16) 0.0294(6) Uani 1 1 d . . . . .
H14 H -0.0887 0.6187 0.1899 0.035 Uiso 1 1 calc R U . . .
C15 C -0.2289(6) 0.7412(3) 0.2899(2) 0.0521(10) Uani 1 1 d . . . . .
H15A H -0.3018 0.6861 0.2769 0.078 Uiso 1 1 calc R U . . .
H15B H -0.3004 0.7971 0.2780 0.078 Uiso 1 1 calc R U . . .
H15C H -0.2007 0.7402 0.3430 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3292(4) 0.4648(2) -0.03715(16) 0.0242(6) Uani 1 1 d . . . . .
C17 C 0.2898(5) 0.3898(2) 0.01060(18) 0.0345(7) Uani 1 1 d . . . . .
H17 H 0.3235 0.3936 0.0614 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2006(6) 0.3087(2) -0.0162(2) 0.0408(8) Uani 1 1 d . . . . .
H18 H 0.1733 0.2593 0.0169 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1522(5) 0.3009(2) -0.0916(2) 0.0374(8) Uani 1 1 d . . . . .
H19 H 0.0940 0.2463 -0.1097 0.045 Uiso 1 1 calc R U . . .
C20 C 0.1909(5) 0.3746(2) -0.13959(18) 0.0374(7) Uani 1 1 d . . . . .
H20 H 0.1583 0.3697 -0.1904 0.045 Uiso 1 1 calc R U . . .
C21 C 0.2780(5) 0.4564(2) -0.11336(17) 0.0316(7) Uani 1 1 d . . . . .
H21 H 0.3025 0.5060 -0.1466 0.038 Uiso 1 1 calc R U . . .
N1 N 0.5857(5) 0.4928(2) 0.17846(17) 0.0484(8) Uani 1 1 d . . . . .
O1 O 0.0729(3) 0.60157(13) 0.03234(10) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.0505 0.6580 0.0261 0.037 Uiso 1 1 calc R U . . .
O2 O 0.4166(3) 0.72020(12) -0.00335(11) 0.0271(5) Uani 1 1 d . . . . .
O3 O 0.4600(3) 0.74820(13) 0.12412(11) 0.0293(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C16 1.521(4) . ?
C1 C2 1.523(4) . ?
C1 C4 1.554(4) . ?
C1 C6 1.575(4) . ?
C2 C3 1.251(6) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?
C3 H3B 0.9300 . ?
C4 O2 1.451(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O3 1.391(3) . ?
C5 O2 1.426(3) . ?
C5 C6 1.546(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.461(4) . ?
C6 C8 1.569(4) . ?
C7 N1 1.147(4) . ?
C8 O1 1.413(3) . ?
C8 C9 1.513(4) . ?
C8 H8 0.9800 . ?
C9 C14 1.391(4) . ?
C9 C10 1.393(4) . ?
C10 O3 1.376(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(4) . ?
C13 C15 1.506(5) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.383(4) . ?
C16 C21 1.400(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O1 H1 0.8200 . ?

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
C16 C1 C2 109.3(2) . . ?
C16 C1 C4 113.5(2) . . ?
C2 C1 C4 108.4(2) . . ?
C16 C1 C6 116.2(2) . . ?
C2 C1 C6 108.7(2) . . ?
C4 C1 C6 100.2(2) . . ?
C3 C2 C1 129.4(4) . . ?
C3 C2 H2 115.3 . . ?
C1 C2 H2 115.3 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
O2 C4 C1 107.3(2) . . ?
O2 C4 H4A 110.3 . . ?
C1 C4 H4A 110.3 . . ?
O2 C4 H4B 110.3 . . ?
C1 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
O3 C5 O2 110.1(2) . . ?
O3 C5 C6 117.2(2) . . ?
O2 C5 C6 103.0(2) . . ?
O3 C5 H5 108.8 . . ?
O2 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C7 C6 C5 109.1(2) . . ?
C7 C6 C8 108.1(2) . . ?
C5 C6 C8 111.0(2) . . ?
C7 C6 C1 114.7(2) . . ?
C5 C6 C1 99.0(2) . . ?
C8 C6 C1 114.6(2) . . ?
N1 C7 C6 176.8(3) . . ?
O1 C8 C9 110.8(2) . . ?
O1 C8 C6 112.8(2) . . ?
C9 C8 C6 110.9(2) . . ?
O1 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C6 C8 H8 107.3 . . ?
C14 C9 C10 118.3(3) . . ?
C14 C9 C8 119.9(3) . . ?
C10 C9 C8 121.7(3) . . ?
O3 C10 C11 115.7(3) . . ?
O3 C10 C9 123.6(2) . . ?
C11 C10 C9 120.7(3) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 C15 121.3(3) . . ?
C12 C13 C15 121.4(3) . . ?
C13 C14 C9 122.4(3) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C1 122.0(3) . . ?
C21 C16 C1 119.5(3) . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C8 O1 H1 109.5 . . ?
C5 O2 C4 108.24(19) . . ?
C10 O3 C5 118.8(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
C16 C1 C2 C3 4.4(7) . . . . ?
C4 C1 C2 C3 -119.8(6) . . . . ?
C6 C1 C2 C3 132.1(6) . . . . ?
C16 C1 C4 O2 144.6(2) . . . . ?
C2 C1 C4 O2 -93.8(3) . . . . ?
C6 C1 C4 O2 20.0(3) . . . . ?
O3 C5 C6 C7 -71.9(3) . . . . ?
O2 C5 C6 C7 167.1(2) . . . . ?
O3 C5 C6 C8 47.0(3) . . . . ?
O2 C5 C6 C8 -73.9(3) . . . . ?
O3 C5 C6 C1 167.9(2) . . . . ?
O2 C5 C6 C1 46.9(2) . . . . ?
C16 C1 C6 C7 82.0(3) . . . . ?
C2 C1 C6 C7 -41.7(3) . . . . ?
C4 C1 C6 C7 -155.2(2) . . . . ?
C16 C1 C6 C5 -162.0(2) . . . . ?
C2 C1 C6 C5 74.3(3) . . . . ?
C4 C1 C6 C5 -39.3(2) . . . . ?
C16 C1 C6 C8 -43.9(3) . . . . ?
C2 C1 C6 C8 -167.6(2) . . . . ?
C4 C1 C6 C8 78.8(3) . . . . ?
C7 C6 C8 O1 -154.3(2) . . . . ?
C5 C6 C8 O1 86.1(2) . . . . ?
C1 C6 C8 O1 -25.0(3) . . . . ?
C7 C6 C8 C9 80.7(3) . . . . ?
C5 C6 C8 C9 -38.9(3) . . . . ?
C1 C6 C8 C9 -150.0(2) . . . . ?
O1 C8 C9 C14 70.6(3) . . . . ?
C6 C8 C9 C14 -163.3(2) . . . . ?
O1 C8 C9 C10 -105.1(3) . . . . ?
C6 C8 C9 C10 20.9(3) . . . . ?
C14 C9 C10 O3 178.6(2) . . . . ?
C8 C9 C10 O3 -5.6(4) . . . . ?
C14 C9 C10 C11 0.6(4) . . . . ?
C8 C9 C10 C11 176.4(3) . . . . ?
O3 C10 C11 C12 -178.7(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C11 C12 C13 C15 -179.1(3) . . . . ?
C12 C13 C14 C9 -1.3(4) . . . . ?
C15 C13 C14 C9 179.2(3) . . . . ?
C10 C9 C14 C13 0.4(4) . . . . ?
C8 C9 C14 C13 -175.5(3) . . . . ?
C2 C1 C16 C17 84.6(3) . . . . ?
C4 C1 C16 C17 -154.2(3) . . . . ?
C6 C1 C16 C17 -38.8(4) . . . . ?
C2 C1 C16 C21 -87.9(3) . . . . ?
C4 C1 C16 C21 33.2(4) . . . . ?
C6 C1 C16 C21 148.7(3) . . . . ?
C21 C16 C17 C18 -0.5(5) . . . . ?
C1 C16 C17 C18 -173.2(3) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C16 0.4(5) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
C1 C16 C21 C20 172.6(3) . . . . ?
O3 C5 O2 C4 -161.6(2) . . . . ?
C6 C5 O2 C4 -36.0(3) . . . . ?
C1 C4 O2 C5 9.5(3) . . . . ?
C11 C10 O3 C5 -171.1(2) . . . . ?
C9 C10 O3 C5 10.8(4) . . . . ?
O2 C5 O3 C10 84.6(3) . . . . ?
C6 C5 O3 C10 -32.5(3) . . . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049

