# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060870'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N4 O2'
_chemical_formula_weight         460.52

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/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                   16.177(3)
_cell_length_b                   7.5746(13)
_cell_length_c                   19.698(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.485(9)
_cell_angle_gamma                90
_cell_volume                     2302.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23137
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.320
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5298
_reflns_number_gt                4685
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0737P)²+0.6158P]
 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         5298
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_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 0.18821(8) 0.08623(17) 0.19410(6) 0.0319(3) Uani 1 1 d . . . . .
H1O H 0.1683 -0.0125 0.1777 0.048 Uiso 1 1 calc R U . . .
C6 C 0.25164(11) -0.0927(2) 0.29813(10) 0.0290(4) Uani 1 1 d . . . . .
H6 H 0.2383 -0.1985 0.2712 0.035 Uiso 1 1 calc R U . . .
O2 O 0.31249(9) 0.37382(19) 0.41251(7) 0.0376(3) Uani 1 1 d . . . . .
H2O H 0.3367 0.3534 0.4559 0.056 Uiso 1 1 calc R U . . .
C2 C 0.25083(10) 0.2286(2) 0.30307(8) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.23021(10) 0.0708(2) 0.26507(8) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.31380(11) 0.0554(3) 0.41040(9) 0.0314(4) Uani 1 1 d . . . . .
H4 H 0.3419 0.0502 0.4602 0.038 Uiso 1 1 calc R U . . .
C3 C 0.29354(11) 0.2180(2) 0.37639(9) 0.0277(4) Uani 1 1 d . . . . .
C5 C 0.29277(11) -0.0988(3) 0.37111(10) 0.0325(4) Uani 1 1 d . . . . .
H5 H 0.3066 -0.2097 0.3942 0.039 Uiso 1 1 calc R U . . .
C7 C 0.22417(13) 0.4027(2) 0.26712(9) 0.0329(4) Uani 1 1 d . . . . .
H7A H 0.2529 0.4198 0.2303 0.049 Uiso 1 1 calc R U . . .
H7B H 0.2410 0.4978 0.3023 0.049 Uiso 1 1 calc R U . . .
H7C H 0.1612 0.4043 0.2452 0.049 Uiso 1 1 calc R U . . .
N3 N 0.07686(9) 0.7773(2) 0.16013(7) 0.0272(3) Uani 1 1 d . . . . .
C29 C 0.05455(11) 0.7937(2) 0.03369(9) 0.0256(3) Uani 1 1 d . . . . .
N4 N 0.13360(10) 0.8700(2) 0.04715(8) 0.0312(3) Uani 1 1 d . . . . .
C18 C 0.02534(11) 0.7400(2) 0.09323(9) 0.0245(3) Uani 1 1 d . . . . .
C22 C -0.05500(11) 0.6522(2) 0.08009(9) 0.0268(4) Uani 1 1 d . . . . .
C25 C -0.00057(11) 0.7621(2) -0.03585(9) 0.0281(4) Uani 1 1 d . . . . .
C21 C -0.08111(12) 0.5988(2) 0.13875(10) 0.0315(4) Uani 1 1 d . . . . .
H21 H -0.1343 0.5379 0.1319 0.038 Uiso 1 1 calc R U . . .
C24 C -0.08228(12) 0.6756(3) -0.04694(9) 0.0329(4) Uani 1 1 d . . . . .
H24 H -0.1187 0.6564 -0.0941 0.040 Uiso 1 1 calc R U . . .
C23 C -0.10833(12) 0.6208(2) 0.00863(9) 0.0313(4) Uani 1 1 d . . . . .
H23 H -0.1622 0.5613 0.0003 0.038 Uiso 1 1 calc R U . . .
C19 C 0.04895(12) 0.7258(2) 0.21392(9) 0.0305(4) Uani 1 1 d . . . . .
H19 H 0.0841 0.7519 0.2609 0.037 Uiso 1 1 calc R U . . .
C20 C -0.02888(13) 0.6355(3) 0.20587(10) 0.0343(4) Uani 1 1 d . . . . .
H20 H -0.0451 0.6005 0.2464 0.041 Uiso 1 1 calc R U . . .
C27 C 0.10901(15) 0.8924(3) -0.07929(10) 0.0398(5) Uani 1 1 d . . . . .
H27 H 0.1299 0.9291 -0.1172 0.048 Uiso 1 1 calc R U . . .
C26 C 0.02916(14) 0.8151(3) -0.09287(10) 0.0360(4) Uani 1 1 d . . . . .
H26 H -0.0060 0.7973 -0.1406 0.043 Uiso 1 1 calc R U . . .
C28 C 0.15917(13) 0.9162(3) -0.00849(10) 0.0368(4) Uani 1 1 d . . . . .
H28 H 0.2148 0.9685 0.0004 0.044 Uiso 1 1 calc R U . . .
C13 C 0.47418(11) 0.6521(2) 0.22027(9) 0.0273(4) Uani 1 1 d . . . . .
C10 C 0.52030(11) 0.6511(2) 0.29751(9) 0.0281(4) Uani 1 1 d . . . . .
C14 C 0.38810(12) 0.7049(3) 0.19472(11) 0.0379(4) Uani 1 1 d . . . . .
H14 H 0.3577 0.7402 0.2269 0.045 Uiso 1 1 calc R U . . .
C17 C 0.51507(12) 0.6025(3) 0.17019(9) 0.0327(4) Uani 1 1 d . . . . .
H17 H 0.5739 0.5654 0.1847 0.039 Uiso 1 1 calc R U . . .
C9 C 0.47684(13) 0.6134(3) 0.34723(10) 0.0384(4) Uani 1 1 d . . . . .
H9 H 0.4170 0.5842 0.3321 0.046 Uiso 1 1 calc R U . . .
C11 C 0.60829(12) 0.6906(3) 0.32358(10) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.6407 0.7165 0.2918 0.042 Uiso 1 1 calc R U . . .
N1 N 0.60641(13) 0.6574(3) 0.44402(9) 0.0480(5) Uani 1 1 d . . . . .
C16 C 0.46779(15) 0.6086(3) 0.09886(11) 0.0450(5) Uani 1 1 d . . . . .
H16 H 0.4964 0.5744 0.0653 0.054 Uiso 1 1 calc R U . . .
N2 N 0.38526(13) 0.6587(3) 0.07368(9) 0.0520(5) Uani 1 1 d . . . . .
C8 C 0.52227(16) 0.6192(3) 0.41876(11) 0.0483(5) Uani 1 1 d . . . . .
H8 H 0.4917 0.5943 0.4520 0.058 Uiso 1 1 calc R U . . .
C12 C 0.64785(14) 0.6916(3) 0.39615(11) 0.0433(5) Uani 1 1 d . . . . .
H12 H 0.7080 0.7180 0.4130 0.052 Uiso 1 1 calc R U . . .
C15 C 0.34690(14) 0.7057(3) 0.12236(12) 0.0483(6) Uani 1 1 d . . . . .
H15 H 0.2880 0.7418 0.1062 0.058 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 1.3633(19) . ?
O1 H1O 0.8400 . ?
C6 C5 1.392(3) . ?
C6 C1 1.393(2) . ?
C6 H6 0.9500 . ?
O2 C3 1.365(2) . ?
O2 H2O 0.8400 . ?
C2 C1 1.397(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.497(2) . ?
C4 C5 1.386(3) . ?
C4 C3 1.393(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N3 C19 1.329(2) . ?
N3 C18 1.360(2) . ?
C29 N4 1.355(2) . ?
C29 C25 1.412(2) . ?
C29 C18 1.448(2) . ?
N4 C28 1.329(2) . ?
C18 C22 1.413(2) . ?
C22 C21 1.404(2) . ?
C22 C23 1.433(2) . ?
C25 C26 1.407(2) . ?
C25 C24 1.432(3) . ?
C21 C20 1.367(3) . ?
C21 H21 0.9500 . ?
C24 C23 1.351(3) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
C19 C20 1.399(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C27 C26 1.369(3) . ?
C27 C28 1.399(3) . ?
C27 H27 0.9500 . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C13 C14 1.390(2) . ?
C13 C17 1.394(2) . ?
C13 C10 1.480(2) . ?
C10 C11 1.393(3) . ?
C10 C9 1.396(2) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C17 C16 1.384(3) . ?
C17 H17 0.9500 . ?
C9 C8 1.380(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
N1 C8 1.333(3) . ?
N1 C12 1.336(3) . ?
C16 N2 1.332(3) . ?
C16 H16 0.9500 . ?
N2 C15 1.337(3) . ?
C8 H8 0.9500 . ?
C12 H12 0.9500 . ?
C15 H15 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
C1 O1 H1O 109.5 . . ?
C5 C6 C1 119.14(16) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C3 O2 H2O 109.5 . . ?
C1 C2 C3 117.82(15) . . ?
C1 C2 C7 120.77(15) . . ?
C3 C2 C7 121.34(15) . . ?
O1 C1 C6 122.18(15) . . ?
O1 C1 C2 116.20(15) . . ?
C6 C1 C2 121.62(15) . . ?
C5 C4 C3 119.57(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O2 C3 C4 122.03(15) . . ?
O2 C3 C2 116.78(15) . . ?
C4 C3 C2 121.17(16) . . ?
C4 C5 C6 120.65(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C19 N3 C18 117.09(15) . . ?
N4 C29 C25 123.08(16) . . ?
N4 C29 C18 118.66(15) . . ?
C25 C29 C18 118.25(15) . . ?
C28 N4 C29 117.39(16) . . ?
N3 C18 C22 122.50(15) . . ?
N3 C18 C29 118.18(15) . . ?
C22 C18 C29 119.32(15) . . ?
C21 C22 C18 118.20(15) . . ?
C21 C22 C23 121.31(16) . . ?
C18 C22 C23 120.49(16) . . ?
C26 C25 C29 117.29(17) . . ?
C26 C25 C24 122.01(16) . . ?
C29 C25 C24 120.68(16) . . ?
C20 C21 C22 119.08(16) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C24 C25 121.02(16) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C23 C22 120.18(17) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
N3 C19 C20 124.24(16) . . ?
N3 C19 H19 117.9 . . ?
C20 C19 H19 117.9 . . ?
C21 C20 C19 118.88(16) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C26 C27 C28 118.73(17) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C26 C25 119.65(17) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N4 C28 C27 123.85(18) . . ?
N4 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
C14 C13 C17 117.26(16) . . ?
C14 C13 C10 120.97(16) . . ?
C17 C13 C10 121.76(16) . . ?
C11 C10 C9 117.36(17) . . ?
C11 C10 C13 121.45(16) . . ?
C9 C10 C13 121.18(17) . . ?
C15 C14 C13 119.73(18) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C17 C13 118.31(17) . . ?
C16 C17 H17 120.8 . . ?
C13 C17 H17 120.8 . . ?
C8 C9 C10 118.93(19) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C12 C11 C10 119.18(18) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C8 N1 C12 116.82(17) . . ?
N2 C16 C17 125.02(19) . . ?
N2 C16 H16 117.5 . . ?
C17 C16 H16 117.5 . . ?
C16 N2 C15 115.97(18) . . ?
N1 C8 C9 123.96(19) . . ?
N1 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
N1 C12 C11 123.73(19) . . ?
N1 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
N2 C15 C14 123.70(19) . . ?
N2 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C1 O1 -178.55(14) . . . . ?
C5 C6 C1 C2 1.5(2) . . . . ?
C3 C2 C1 O1 179.54(14) . . . . ?
C7 C2 C1 O1 2.5(2) . . . . ?
C3 C2 C1 C6 -0.5(2) . . . . ?
C7 C2 C1 C6 -177.59(16) . . . . ?
C5 C4 C3 O2 179.77(16) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C1 C2 C3 O2 -179.55(14) . . . . ?
C7 C2 C3 O2 -2.5(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C7 C2 C3 C4 176.27(16) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C25 C29 N4 C28 0.0(3) . . . . ?
C18 C29 N4 C28 179.29(16) . . . . ?
C19 N3 C18 C22 0.6(2) . . . . ?
C19 N3 C18 C29 -179.59(15) . . . . ?
N4 C29 C18 N3 3.4(2) . . . . ?
C25 C29 C18 N3 -177.25(14) . . . . ?
N4 C29 C18 C22 -176.81(15) . . . . ?
C25 C29 C18 C22 2.6(2) . . . . ?
N3 C18 C22 C21 -1.3(2) . . . . ?
C29 C18 C22 C21 178.87(16) . . . . ?
N3 C18 C22 C23 178.01(16) . . . . ?
C29 C18 C22 C23 -1.8(2) . . . . ?
N4 C29 C25 C26 -0.6(3) . . . . ?
C18 C29 C25 C26 -179.91(15) . . . . ?
N4 C29 C25 C24 177.90(16) . . . . ?
C18 C29 C25 C24 -1.4(2) . . . . ?
C18 C22 C21 C20 0.9(3) . . . . ?
C23 C22 C21 C20 -178.43(17) . . . . ?
C26 C25 C24 C23 177.86(18) . . . . ?
C29 C25 C24 C23 -0.5(3) . . . . ?
C25 C24 C23 C22 1.4(3) . . . . ?
C21 C22 C23 C24 179.12(17) . . . . ?
C18 C22 C23 C24 -0.2(3) . . . . ?
C18 N3 C19 C20 0.5(3) . . . . ?
C22 C21 C20 C19 0.1(3) . . . . ?
N3 C19 C20 C21 -0.9(3) . . . . ?
C28 C27 C26 C25 0.2(3) . . . . ?
C29 C25 C26 C27 0.5(3) . . . . ?
C24 C25 C26 C27 -177.96(18) . . . . ?
C29 N4 C28 C27 0.8(3) . . . . ?
C26 C27 C28 N4 -0.8(3) . . . . ?
C14 C13 C10 C11 -145.8(2) . . . . ?
C17 C13 C10 C11 33.4(3) . . . . ?
C14 C13 C10 C9 33.1(3) . . . . ?
C17 C13 C10 C9 -147.7(2) . . . . ?
C17 C13 C14 C15 0.2(3) . . . . ?
C10 C13 C14 C15 179.50(19) . . . . ?
C14 C13 C17 C16 -0.1(3) . . . . ?
C10 C13 C17 C16 -179.35(18) . . . . ?
C11 C10 C9 C8 0.8(3) . . . . ?
C13 C10 C9 C8 -178.17(18) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C13 C10 C11 C12 178.63(18) . . . . ?
C13 C17 C16 N2 0.0(3) . . . . ?
C17 C16 N2 C15 -0.1(4) . . . . ?
C12 N1 C8 C9 -0.1(4) . . . . ?
C10 C9 C8 N1 -0.6(4) . . . . ?
C8 N1 C12 C11 0.6(3) . . . . ?
C10 C11 C12 N1 -0.4(3) . . . . ?
C16 N2 C15 C14 0.2(4) . . . . ?
C13 C14 C15 N2 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 N2 0.95 2.66 3.475(3) 144.8 4_566
C15 H15 N4 0.95 2.61 3.547(3) 171.0 .
O2 H2O N1 0.84 1.91 2.745(2) 171.8 3_666
O1 H1O N3 0.84 2.13 2.906(2) 153.7 1_545
O1 H1O N4 0.84 2.62 3.210(2) 128.6 1_545
C4 H4 N2 0.95 2.66 3.475(3) 144.8 4_566
C15 H15 N4 0.95 2.61 3.547(3) 171.0 .
O2 H2O N1 0.84 1.91 2.745(2) 171.8 3_666
O1 H1O N3 0.84 2.13 2.906(2) 153.7 1_545
O1 H1O N4 0.84 2.62 3.210(2) 128.6 1_545
C4 H4 N2 0.95 2.66 3.475(3) 144.8 4_566
C15 H15 N4 0.95 2.61 3.547(3) 171.0 .
O1 H1O N3 0.84 2.13 2.906(2) 153.7 1_545
O1 H1O N4 0.84 2.62 3.210(2) 128.6 1_545
O2 H2O N1 0.84 1.91 2.745(2) 171.8 3_666
C4 H4 N2 0.95 2.66 3.475(3) 144.8 4_566
C15 H15 N4 0.95 2.61 3.547(3) 171.0 .

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060871'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 N3 O2'
_chemical_formula_weight         459.53

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/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                   16.337(13)
_cell_length_b                   7.599(6)
_cell_length_c                   19.883(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.782(9)
_cell_angle_gamma                90
_cell_volume                     2350(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24193
_diffrn_reflns_av_unetI/netI     0.1293
_diffrn_reflns_av_R_equivalents  0.1583
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.309
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5409
_reflns_number_gt                3029
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1055P)²+0.1974P]
 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         5409
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.2727
_refine_ls_wR_factor_gt          0.2147
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.31741(19) 0.6092(3) 0.30713(14) 0.0325(7) Uani 1 1 d . . . . .
H1 H 0.3320 0.5094 0.3249 0.049 Uiso 1 1 calc R U . . .
C29 C 0.5543(3) 0.8002(5) 0.0314(2) 0.0269(9) Uani 1 1 d . . . . .
O2 O 0.1878(2) 0.8862(4) 0.08768(15) 0.0395(8) Uani 1 1 d . . . . .
H2 H 0.1701 0.8630 0.0443 0.059 Uiso 1 1 calc R U . . .
N1 N 0.5734(2) 0.7993(4) 0.15658(17) 0.0294(8) Uani 1 1 d . . . . .
C3 C 0.2511(2) 0.4259(5) 0.2051(2) 0.0274(9) Uani 1 1 d . . . . .
H3 H 0.2662 0.3214 0.2322 0.033 Uiso 1 1 calc R U . . .
C30 C 0.5237(2) 0.7546(5) 0.0905(2) 0.0261(9) Uani 1 1 d . . . . .
C1 C 0.2514(2) 0.7466(5) 0.1980(2) 0.0245(8) Uani 1 1 d . . . . .
C22 C 0.4455(3) 0.6648(5) 0.0776(2) 0.0284(9) Uani 1 1 d . . . . .
C24 C 0.4219(3) 0.6693(5) -0.0485(2) 0.0326(10) Uani 1 1 d . . . . .
H24 H 0.3875 0.6423 -0.0952 0.039 Uiso 1 1 calc R U . . .
N2 N 0.6322(2) 0.8817(4) 0.04470(18) 0.0335(8) Uani 1 1 d . . . . .
C2 C 0.2726(2) 0.5911(5) 0.23686(19) 0.0236(8) Uani 1 1 d . . . . .
C25 C 0.5027(3) 0.7585(5) -0.0377(2) 0.0302(9) Uani 1 1 d . . . . .
C23 C 0.3942(3) 0.6234(5) 0.0062(2) 0.0338(10) Uani 1 1 d . . . . .
H23 H 0.3409 0.5637 -0.0021 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2066(3) 0.7333(5) 0.1254(2) 0.0270(9) Uani 1 1 d . . . . .
C21 C 0.4180(3) 0.6200(5) 0.1355(2) 0.0334(10) Uani 1 1 d . . . . .
H21 H 0.3656 0.5583 0.1286 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2071(3) 0.4174(5) 0.1331(2) 0.0324(10) Uani 1 1 d . . . . .
H4 H 0.1923 0.3060 0.1110 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1846(3) 0.5697(5) 0.0932(2) 0.0312(9) Uani 1 1 d . . . . .
H5 H 0.1544 0.5625 0.0442 0.037 Uiso 1 1 calc R U . . .
C27 C 0.6128(3) 0.8820(6) -0.0801(2) 0.0398(11) Uani 1 1 d . . . . .
H27 H 0.6353 0.9121 -0.1173 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2775(3) 0.9227(5) 0.2329(2) 0.0328(10) Uani 1 1 d . . . . .
H7A H 0.2545 0.9351 0.2728 0.049 Uiso 1 1 calc R U . . .
H7B H 0.2546 1.0168 0.1986 0.049 Uiso 1 1 calc R U . . .
H7C H 0.3403 0.9307 0.2500 0.049 Uiso 1 1 calc R U . . .
C28 C 0.6589(3) 0.9190(6) -0.0102(2) 0.0373(10) Uani 1 1 d . . . . .
H28 H 0.7132 0.9748 -0.0014 0.045 Uiso 1 1 calc R U . . .
C20 C 0.4675(3) 0.6659(6) 0.2024(2) 0.0361(10) Uani 1 1 d . . . . .
H20 H 0.4498 0.6373 0.2423 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5444(3) 0.7555(5) 0.2103(2) 0.0331(10) Uani 1 1 d . . . . .
H19 H 0.5782 0.7873 0.2567 0.040 Uiso 1 1 calc R U . . .
C26 C 0.5345(3) 0.8013(6) -0.0940(2) 0.0379(11) Uani 1 1 d . . . . .
H26 H 0.5019 0.7745 -0.1412 0.046 Uiso 1 1 calc R U . . .
C13 C 0.0257(3) 0.1635(5) 0.2759(2) 0.0278(9) Uani 1 1 d . . . . .
C10 C -0.0247(3) 0.1593(5) 0.1993(2) 0.0273(9) Uani 1 1 d . . . . .
C18 C -0.0111(3) 0.1170(5) 0.3282(2) 0.0325(10) Uani 1 1 d . . . . .
H18 H -0.0692 0.0784 0.3151 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1119(3) 0.2164(6) 0.2971(2) 0.0368(10) Uani 1 1 d . . . . .
H14 H 0.1388 0.2453 0.2624 0.044 Uiso 1 1 calc R U . . .
C11 C -0.1110(3) 0.2008(5) 0.1752(2) 0.0333(10) Uani 1 1 d . . . . .
H11 H -0.1410 0.2305 0.2078 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0148(3) 0.1173(6) 0.1481(2) 0.0378(10) Uani 1 1 d . . . . .
H9 H 0.0740 0.0868 0.1616 0.045 Uiso 1 1 calc R U . . .
N3 N -0.1163(3) 0.1604(5) 0.05424(19) 0.0438(10) Uani 1 1 d . . . . .
C16 C 0.1210(3) 0.1810(6) 0.4191(2) 0.0472(13) Uani 1 1 d . . . . .
H16 H 0.1532 0.1864 0.4677 0.057 Uiso 1 1 calc R U . . .
C17 C 0.0364(3) 0.1265(6) 0.3993(2) 0.0439(12) Uani 1 1 d . . . . .
H17 H 0.0106 0.0953 0.4344 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1535(3) 0.1990(6) 0.1036(2) 0.0403(11) Uani 1 1 d . . . . .
H12 H -0.2130 0.2269 0.0885 0.048 Uiso 1 1 calc R U . . .
C8 C -0.0331(4) 0.1208(6) 0.0779(2) 0.0481(13) Uani 1 1 d . . . . .
H8 H -0.0048 0.0929 0.0440 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1589(3) 0.2274(6) 0.3685(2) 0.0449(12) Uani 1 1 d . . . . .
H15 H 0.2168 0.2668 0.3822 0.054 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 C2 1.372(4) . ?
O1 H1 0.8400 . ?
C29 N2 1.366(5) . ?
C29 C25 1.411(5) . ?
C29 C30 1.451(6) . ?
O2 C6 1.366(5) . ?
O2 H2 0.8400 . ?
N1 C19 1.337(5) . ?
N1 C30 1.361(5) . ?
C3 C4 1.394(6) . ?
C3 C2 1.401(5) . ?
C3 H3 0.9500 . ?
C30 C22 1.402(6) . ?
C1 C2 1.396(5) . ?
C1 C6 1.410(5) . ?
C1 C7 1.508(5) . ?
C22 C21 1.399(6) . ?
C22 C23 1.446(6) . ?
C24 C23 1.346(6) . ?
C24 C25 1.440(6) . ?
C24 H24 0.9500 . ?
N2 C28 1.325(5) . ?
C25 C26 1.409(6) . ?
C23 H23 0.9500 . ?
C6 C5 1.394(5) . ?
C21 C20 1.373(6) . ?
C21 H21 0.9500 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C27 C26 1.368(7) . ?
C27 C28 1.391(6) . ?
C27 H27 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C28 H28 0.9500 . ?
C20 C19 1.395(6) . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C26 H26 0.9500 . ?
C13 C18 1.396(6) . ?
C13 C14 1.400(6) . ?
C13 C10 1.495(5) . ?
C10 C11 1.380(6) . ?
C10 C9 1.399(6) . ?
C18 C17 1.392(6) . ?
C18 H18 0.9500 . ?
C14 C15 1.394(6) . ?
C14 H14 0.9500 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C9 C8 1.377(7) . ?
C9 H9 0.9500 . ?
N3 C8 1.330(7) . ?
N3 C12 1.335(6) . ?
C16 C15 1.377(7) . ?
C16 C17 1.380(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
N2 C29 C25 122.3(4) . . ?
N2 C29 C30 118.9(3) . . ?
C25 C29 C30 118.9(4) . . ?
C6 O2 H2 109.5 . . ?
C19 N1 C30 117.2(4) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N1 C30 C22 122.6(4) . . ?
N1 C30 C29 118.1(3) . . ?
C22 C30 C29 119.3(4) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C7 120.6(3) . . ?
C6 C1 C7 121.3(3) . . ?
C21 C22 C30 118.2(4) . . ?
C21 C22 C23 121.3(4) . . ?
C30 C22 C23 120.5(4) . . ?
C23 C24 C25 121.4(4) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C28 N2 C29 117.4(4) . . ?
O1 C2 C1 116.4(3) . . ?
O1 C2 C3 122.1(3) . . ?
C1 C2 C3 121.6(3) . . ?
C26 C25 C29 117.8(4) . . ?
C26 C25 C24 122.3(4) . . ?
C29 C25 C24 119.9(4) . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
O2 C6 C5 121.6(4) . . ?
O2 C6 C1 117.4(3) . . ?
C5 C6 C1 121.0(4) . . ?
C20 C21 C22 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C26 C27 C28 118.7(4) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C28 C27 124.4(4) . . ?
N2 C28 H28 117.8 . . ?
C27 C28 H28 117.8 . . ?
C21 C20 C19 118.5(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N1 C19 C20 123.9(4) . . ?
N1 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C18 C13 C14 118.1(4) . . ?
C18 C13 C10 121.7(4) . . ?
C14 C13 C10 120.2(4) . . ?
C11 C10 C9 116.7(4) . . ?
C11 C10 C13 122.3(4) . . ?
C9 C10 C13 120.9(4) . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C8 N3 C12 115.8(4) . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
N3 C12 C11 124.2(4) . . ?
N3 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N3 C8 C9 124.4(5) . . ?
N3 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N1 C30 C22 -0.6(6) . . . . ?
C19 N1 C30 C29 -179.7(3) . . . . ?
N2 C29 C30 N1 1.6(5) . . . . ?
C25 C29 C30 N1 -178.6(3) . . . . ?
N2 C29 C30 C22 -177.5(4) . . . . ?
C25 C29 C30 C22 2.3(5) . . . . ?
N1 C30 C22 C21 0.0(6) . . . . ?
C29 C30 C22 C21 179.1(3) . . . . ?
N1 C30 C22 C23 178.8(4) . . . . ?
C29 C30 C22 C23 -2.1(6) . . . . ?
C25 C29 N2 C28 -0.9(6) . . . . ?
C30 C29 N2 C28 178.9(4) . . . . ?
C6 C1 C2 O1 179.0(4) . . . . ?
C7 C1 C2 O1 0.2(5) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C7 C1 C2 C3 -178.2(4) . . . . ?
C4 C3 C2 O1 -178.6(4) . . . . ?
C4 C3 C2 C1 -0.3(6) . . . . ?
N2 C29 C25 C26 0.9(6) . . . . ?
C30 C29 C25 C26 -178.9(3) . . . . ?
N2 C29 C25 C24 178.7(4) . . . . ?
C30 C29 C25 C24 -1.1(5) . . . . ?
C23 C24 C25 C26 177.4(4) . . . . ?
C23 C24 C25 C29 -0.3(6) . . . . ?
C25 C24 C23 C22 0.5(6) . . . . ?
C21 C22 C23 C24 179.5(4) . . . . ?
C30 C22 C23 C24 0.7(6) . . . . ?
C2 C1 C6 O2 -178.7(3) . . . . ?
C7 C1 C6 O2 0.1(6) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
C7 C1 C6 C5 178.4(4) . . . . ?
C30 C22 C21 C20 0.5(6) . . . . ?
C23 C22 C21 C20 -178.3(4) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
O2 C6 C5 C4 178.2(4) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C29 N2 C28 C27 0.5(6) . . . . ?
C26 C27 C28 N2 -0.1(7) . . . . ?
C22 C21 C20 C19 -0.4(6) . . . . ?
C30 N1 C19 C20 0.8(6) . . . . ?
C21 C20 C19 N1 -0.3(7) . . . . ?
C28 C27 C26 C25 0.1(6) . . . . ?
C29 C25 C26 C27 -0.5(6) . . . . ?
C24 C25 C26 C27 -178.3(4) . . . . ?
C18 C13 C10 C11 34.7(6) . . . . ?
C14 C13 C10 C11 -144.8(4) . . . . ?
C18 C13 C10 C9 -147.2(4) . . . . ?
C14 C13 C10 C9 33.3(6) . . . . ?
C14 C13 C18 C17 1.2(6) . . . . ?
C10 C13 C18 C17 -178.3(4) . . . . ?
C18 C13 C14 C15 -1.9(6) . . . . ?
C10 C13 C14 C15 177.6(4) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C13 C10 C11 C12 178.3(4) . . . . ?
C11 C10 C9 C8 0.5(6) . . . . ?
C13 C10 C9 C8 -177.8(4) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C13 C18 C17 C16 -0.5(7) . . . . ?
C8 N3 C12 C11 0.5(7) . . . . ?
C10 C11 C12 N3 -0.6(7) . . . . ?
C12 N3 C8 C9 0.1(7) . . . . ?
C10 C9 C8 N3 -0.6(7) . . . . ?
C17 C16 C15 C14 -1.1(7) . . . . ?
C13 C14 C15 C16 1.9(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 2.17 2.909(4) 146.1 2_645
O1 H1 N2 0.84 2.66 3.296(5) 133.6 2_645
O2 H2 N3 0.84 1.90 2.728(5) 170.6 3_565

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060872'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 O2'
_chemical_formula_weight         124.13

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/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                   9.117(6)
_cell_length_b                   11.604(8)
_cell_length_c                   18.108(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.885(8)
_cell_angle_gamma                90
_cell_volume                     1913(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            19457
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4409
_reflns_number_gt                4019
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0743P)²+0.5692P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4409
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1547
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
H5O H 1.311(3) 0.655(2) 0.4169(14) 0.051(7) Uiso 1 1 d . . . . .
H4O H 0.599(3) 0.301(2) 0.4676(13) 0.049(6) Uiso 1 1 d . . . . .
H2O H 0.608(3) 0.303(2) 0.0444(14) 0.056(7) Uiso 1 1 d . . . . .
H3O H 1.044(4) 0.663(3) 0.3998(16) 0.067(9) Uiso 1 1 d . . . . .
H1O H 1.065(4) 0.667(2) 0.0845(15) 0.063(8) Uiso 1 1 d . . . . .
H6O H 1.324(4) 0.660(3) 0.0780(17) 0.068(8) Uiso 1 1 d . . . . .
O1 O 0.98682(13) 0.65998(10) 0.06426(7) 0.0315(3) Uani 1 1 d . . . . .
O3 O 0.97079(14) 0.65698(10) 0.42156(7) 0.0352(3) Uani 1 1 d . . . . .
O5 O 1.25675(14) 0.66771(11) 0.37532(7) 0.0343(3) Uani 1 1 d . . . . .
O6 O 1.28062(14) 0.67948(11) 0.11594(7) 0.0341(3) Uani 1 1 d . . . . .
O4 O 0.62881(13) 0.36896(11) 0.48315(6) 0.0315(3) Uani 1 1 d . . . . .
O2 O 0.62864(13) 0.36762(11) 0.02587(7) 0.0342(3) Uani 1 1 d . . . . .
C16 C 1.27005(16) 0.67503(13) 0.24574(9) 0.0266(3) Uani 1 1 d . . . . .
C17 C 1.34236(17) 0.64244(13) 0.18291(9) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.79795(16) 0.51421(13) 0.45236(8) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.80445(16) 0.51592(13) 0.04607(8) 0.0260(3) Uani 1 1 d . . . . .
C3 C 0.75453(16) 0.40640(14) 0.06381(8) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.82898(19) 0.33600(14) 0.11543(9) 0.0312(3) Uani 1 1 d . . . . .
H4 H 0.7924 0.2617 0.1266 0.037 Uiso 1 1 calc R U . . .
C15 C 1.32912(17) 0.63567(13) 0.31359(8) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.93454(16) 0.55268(13) 0.08234(8) 0.0262(3) Uani 1 1 d . . . . .
C11 C 0.7809(2) 0.33697(14) 0.38037(9) 0.0339(4) Uani 1 1 d . . . . .
H11 H 0.7368 0.2638 0.3714 0.041 Uiso 1 1 calc R U . . .
C6 C 1.01082(18) 0.48474(14) 0.13429(9) 0.0308(3) Uani 1 1 d . . . . .
H6 H 1.0987 0.5122 0.1587 0.037 Uiso 1 1 calc R U . . .
C5 C 0.95712(19) 0.37649(15) 0.14999(9) 0.0322(4) Uani 1 1 d . . . . .
H5 H 1.0093 0.3292 0.1852 0.039 Uiso 1 1 calc R U . . .
C7 C 0.72417(18) 0.59089(14) -0.01041(9) 0.0319(3) Uani 1 1 d . . . . .
H7A H 0.6774 0.6550 0.0146 0.048 Uiso 1 1 calc R U . . .
H7B H 0.6489 0.5452 -0.0376 0.048 Uiso 1 1 calc R U . . .
H7C H 0.7939 0.6213 -0.0450 0.048 Uiso 1 1 calc R U . . .
C10 C 0.73622(17) 0.40628(13) 0.43765(8) 0.0269(3) Uani 1 1 d . . . . .
C19 C 1.52684(18) 0.54159(16) 0.25600(10) 0.0350(4) Uani 1 1 d . . . . .
H19 H 1.6149 0.4978 0.2596 0.042 Uiso 1 1 calc R U . . .
C8 C 0.90826(17) 0.55024(13) 0.40685(9) 0.0286(3) Uani 1 1 d . . . . .
C18 C 1.46968(18) 0.57671(15) 0.18719(10) 0.0328(4) Uani 1 1 d . . . . .
H18 H 1.5171 0.5560 0.1436 0.039 Uiso 1 1 calc R U . . .
C13 C 0.9545(2) 0.48282(16) 0.34909(10) 0.0371(4) Uani 1 1 d . . . . .
H13 H 1.0291 0.5096 0.3186 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7493(2) 0.58872(14) 0.51455(10) 0.0341(4) Uani 1 1 d . . . . .
H14A H 0.6935 0.6546 0.4942 0.051 Uiso 1 1 calc R U . . .
H14B H 0.8356 0.6165 0.5437 0.051 Uiso 1 1 calc R U . . .
H14C H 0.6870 0.5436 0.5463 0.051 Uiso 1 1 calc R U . . .
C20 C 1.45632(18) 0.56995(14) 0.31949(9) 0.0318(3) Uani 1 1 d . . . . .
H20 H 1.4946 0.5447 0.3665 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8903(2) 0.37622(16) 0.33669(10) 0.0400(4) Uani 1 1 d . . . . .
H12 H 0.9219 0.3293 0.2976 0.048 Uiso 1 1 calc R U . . .
C21 C 1.1379(2) 0.75321(17) 0.24103(10) 0.0395(4) Uani 1 1 d . . . . .
H21A H 1.0482 0.7066 0.2368 0.059 Uiso 1 1 calc R U . . .
H21B H 1.1426 0.8030 0.1975 0.059 Uiso 1 1 calc R U . . .
H21C H 1.1369 0.8009 0.2857 0.059 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 1.379(2) . ?
O1 H1O 0.79(3) . ?
O3 C8 1.384(2) . ?
O3 H3O 0.80(3) . ?
O5 C15 1.377(2) . ?
O5 H5O 0.89(3) . ?
O6 C17 1.380(2) . ?
O6 H6O 0.84(3) . ?
O4 C10 1.381(2) . ?
O4 H4O 0.88(3) . ?
O2 C3 1.383(2) . ?
O2 H2O 0.84(3) . ?
C16 C15 1.393(2) . ?
C16 C17 1.396(2) . ?
C16 C21 1.507(2) . ?
C17 C18 1.388(2) . ?
C9 C10 1.393(2) . ?
C9 C8 1.396(2) . ?
C9 C14 1.504(2) . ?
C2 C3 1.393(2) . ?
C2 C1 1.393(2) . ?
C2 C7 1.504(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C15 C20 1.388(2) . ?
C1 C6 1.387(2) . ?
C11 C12 1.381(3) . ?
C11 C10 1.390(2) . ?
C11 H11 0.9500 . ?
C6 C5 1.383(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C19 C20 1.385(3) . ?
C19 C18 1.387(2) . ?
C19 H19 0.9500 . ?
C8 C13 1.389(2) . ?
C18 H18 0.9500 . ?
C13 C12 1.382(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 H20 0.9500 . ?
C12 H12 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 108(2) . . ?
C8 O3 H3O 110(2) . . ?
C15 O5 H5O 111.7(17) . . ?
C17 O6 H6O 117(2) . . ?
C10 O4 H4O 108.1(16) . . ?
C3 O2 H2O 106.6(18) . . ?
C15 C16 C17 116.91(15) . . ?
C15 C16 C21 121.31(15) . . ?
C17 C16 C21 121.73(15) . . ?
O6 C17 C18 121.56(15) . . ?
O6 C17 C16 116.34(15) . . ?
C18 C17 C16 122.11(15) . . ?
C10 C9 C8 116.90(14) . . ?
C10 C9 C14 121.89(14) . . ?
C8 C9 C14 121.22(15) . . ?
C3 C2 C1 116.80(14) . . ?
C3 C2 C7 122.07(14) . . ?
C1 C2 C7 121.12(14) . . ?
O2 C3 C4 120.47(15) . . ?
O2 C3 C2 117.06(14) . . ?
C4 C3 C2 122.43(15) . . ?
C5 C4 C3 118.55(15) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
O5 C15 C20 121.22(14) . . ?
O5 C15 C16 116.58(15) . . ?
C20 C15 C16 122.17(15) . . ?
O1 C1 C6 120.45(15) . . ?
O1 C1 C2 117.44(13) . . ?
C6 C1 C2 122.11(15) . . ?
C12 C11 C10 118.93(16) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C5 C6 C1 119.02(16) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C5 C6 121.09(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C10 C11 120.47(15) . . ?
O4 C10 C9 117.36(14) . . ?
C11 C10 C9 122.16(15) . . ?
C20 C19 C18 120.45(16) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
O3 C8 C13 120.76(15) . . ?
O3 C8 C9 117.16(14) . . ?
C13 C8 C9 122.08(16) . . ?
C19 C18 C17 119.13(16) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C12 C13 C8 118.98(16) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C20 C15 119.20(15) . . ?
C19 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?
C11 C12 C13 120.95(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C16 C17 O6 178.38(13) . . . . ?
C21 C16 C17 O6 -4.1(2) . . . . ?
C15 C16 C17 C18 -1.8(2) . . . . ?
C21 C16 C17 C18 175.70(16) . . . . ?
C1 C2 C3 O2 -177.51(13) . . . . ?
C7 C2 C3 O2 1.4(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C7 C2 C3 C4 179.31(14) . . . . ?
O2 C3 C4 C5 177.61(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C17 C16 C15 O5 -179.69(13) . . . . ?
C21 C16 C15 O5 2.8(2) . . . . ?
C17 C16 C15 C20 1.9(2) . . . . ?
C21 C16 C15 C20 -175.65(16) . . . . ?
C3 C2 C1 O1 178.74(13) . . . . ?
C7 C2 C1 O1 -0.2(2) . . . . ?
C3 C2 C1 C6 -0.7(2) . . . . ?
C7 C2 C1 C6 -179.63(15) . . . . ?
O1 C1 C6 C5 -178.59(14) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C1 C6 C5 C4 -0.6(2) . . . . ?
C12 C11 C10 O4 -178.94(16) . . . . ?
C12 C11 C10 C9 0.2(3) . . . . ?
C8 C9 C10 O4 178.90(13) . . . . ?
C14 C9 C10 O4 -0.8(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C14 C9 C10 C11 -179.90(15) . . . . ?
C10 C9 C8 O3 -179.51(13) . . . . ?
C14 C9 C8 O3 0.1(2) . . . . ?
C10 C9 C8 C13 0.5(2) . . . . ?
C14 C9 C8 C13 -179.87(16) . . . . ?
C20 C19 C18 C17 1.2(3) . . . . ?
O6 C17 C18 C19 -179.87(15) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
O3 C8 C13 C12 179.35(16) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C18 C19 C20 C15 -1.1(3) . . . . ?
O5 C15 C20 C19 -178.82(15) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C8 C13 C12 C11 0.6(3) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060873'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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'
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                   7.6951(10)
_cell_length_b                   20.299(2)
_cell_length_c                   9.0890(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.677(6)
_cell_angle_gamma                90
_cell_volume                     1418.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14611
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.007
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3239
_reflns_number_gt                2866
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0932P)²+0.2605P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3239
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1697
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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
H1O H 0.934(3) 0.3030(11) 0.664(2) 0.043(5) Uiso 1 1 d . . . . .
H2O H 0.637(3) 0.1078(13) 0.220(3) 0.061(7) Uiso 1 1 d . . . . .
O2 O 0.60926(14) 0.14528(5) 0.26046(11) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.83977(15) 0.28973(5) 0.62541(12) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.72543(17) 0.21837(6) 0.44274(14) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.87198(18) 0.24526(6) 0.51746(14) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.9210(2) 0.15251(7) 0.29875(15) 0.0283(3) Uani 1 1 d . . . . .
H3 H 0.9375 0.1209 0.2236 0.034 Uiso 1 1 calc R U . . .
C2 C 0.75349(18) 0.17170(6) 0.33316(14) 0.0234(3) Uani 1 1 d . . . . .
N1 N 0.67073(16) 0.02087(6) 0.18519(13) 0.0270(3) Uani 1 1 d . . . . .
C5 C 1.04036(19) 0.22651(7) 0.48464(16) 0.0293(3) Uani 1 1 d . . . . .
H5 H 1.1382 0.2453 0.5366 0.035 Uiso 1 1 calc R U . . .
C4 C 1.06302(19) 0.18012(8) 0.37538(16) 0.0309(3) Uani 1 1 d . . . . .
H4 H 1.1773 0.1671 0.3527 0.037 Uiso 1 1 calc R U . . .
C12 C 0.72878(18) -0.01549(7) 0.07357(15) 0.0245(3) Uani 1 1 d . . . . .
C13 C 0.76513(18) 0.01917(7) -0.06654(15) 0.0252(3) Uani 1 1 d . . . . .
C7 C 0.54476(19) 0.23824(8) 0.48253(18) 0.0321(3) Uani 1 1 d . . . . .
H7A H 0.5180 0.2820 0.4422 0.048 Uiso 1 1 calc R U . . .
H7B H 0.5385 0.2393 0.5900 0.048 Uiso 1 1 calc R U . . .
H7C H 0.4603 0.2063 0.4413 0.048 Uiso 1 1 calc R U . . .
N2 N 0.83395(18) -0.01835(6) -0.17140(14) 0.0331(3) Uani 1 1 d . . . . .
C14 C 0.7312(2) 0.08594(7) -0.08790(16) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.6822 0.1113 -0.0124 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7552(2) -0.08312(7) 0.08848(17) 0.0318(3) Uani 1 1 d . . . . .
H11 H 0.7953 -0.1082 0.0086 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6394(2) -0.00933(8) 0.31211(17) 0.0324(3) Uani 1 1 d . . . . .
H8 H 0.5979 0.0165 0.3903 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6641(2) -0.07598(8) 0.33555(18) 0.0375(4) Uani 1 1 d . . . . .
H9 H 0.6418 -0.0955 0.4277 0.045 Uiso 1 1 calc R U . . .
C17 C 0.8694(2) 0.01054(9) -0.29801(18) 0.0372(4) Uani 1 1 d . . . . .
H17 H 0.9176 -0.0158 -0.3723 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7696(2) 0.11492(8) -0.22042(17) 0.0366(4) Uani 1 1 d . . . . .
H15 H 0.7477 0.1604 -0.2370 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8402(2) 0.07664(9) -0.32821(17) 0.0365(4) Uani 1 1 d . . . . .
H16 H 0.8679 0.0951 -0.4203 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7225(2) -0.11333(8) 0.22045(19) 0.0384(4) Uani 1 1 d . . . . .
H10 H 0.7399 -0.1594 0.2321 0.046 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
O2 C2 1.3739(17) . ?
O2 H2O 0.88(3) . ?
O1 C6 1.3644(16) . ?
O1 H1O 0.84(2) . ?
C1 C2 1.3987(18) . ?
C1 C6 1.3997(19) . ?
C1 C7 1.508(2) . ?
C6 C5 1.396(2) . ?
C3 C4 1.386(2) . ?
C3 C2 1.396(2) . ?
C3 H3 0.9500 . ?
N1 C8 1.3382(18) . ?
N1 C12 1.3476(17) . ?
C5 C4 1.385(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C12 C11 1.393(2) . ?
C12 C13 1.493(2) . ?
C13 N2 1.3475(18) . ?
C13 C14 1.392(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N2 C17 1.331(2) . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C11 C10 1.381(2) . ?
C11 H11 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C17 C16 1.386(2) . ?
C17 H17 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H2O 109.7(16) . . ?
C6 O1 H1O 109.4(15) . . ?
C2 C1 C6 117.51(12) . . ?
C2 C1 C7 121.79(12) . . ?
C6 C1 C7 120.68(12) . . ?
O1 C6 C5 122.38(13) . . ?
O1 C6 C1 115.95(12) . . ?
C5 C6 C1 121.65(13) . . ?
C4 C3 C2 119.28(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
O2 C2 C3 121.13(12) . . ?
O2 C2 C1 117.31(12) . . ?
C3 C2 C1 121.56(13) . . ?
C8 N1 C12 118.52(12) . . ?
C4 C5 C6 119.19(13) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C4 C3 120.81(13) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C12 C11 121.22(13) . . ?
N1 C12 C13 117.77(13) . . ?
C11 C12 C13 121.00(13) . . ?
N2 C13 C14 121.93(13) . . ?
N2 C13 C12 115.63(13) . . ?
C14 C13 C12 122.44(13) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C17 N2 C13 117.75(14) . . ?
C15 C14 C13 119.25(14) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C10 C11 C12 119.38(14) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N1 C8 C9 123.54(14) . . ?
N1 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C8 C9 C10 117.86(14) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C17 C16 124.06(15) . . ?
N2 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
C16 C15 C14 119.00(15) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 118.01(14) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C11 C10 C9 119.48(14) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 O1 -178.86(11) . . . . ?
C7 C1 C6 O1 -0.27(19) . . . . ?
C2 C1 C6 C5 -0.01(19) . . . . ?
C7 C1 C6 C5 178.58(13) . . . . ?
C4 C3 C2 O2 -179.63(12) . . . . ?
C4 C3 C2 C1 0.3(2) . . . . ?
C6 C1 C2 O2 179.79(11) . . . . ?
C7 C1 C2 O2 1.22(19) . . . . ?
C6 C1 C2 C3 -0.14(19) . . . . ?
C7 C1 C2 C3 -178.71(13) . . . . ?
O1 C6 C5 C4 178.78(12) . . . . ?
C1 C6 C5 C4 0.0(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C8 N1 C12 C11 0.3(2) . . . . ?
C8 N1 C12 C13 -179.26(12) . . . . ?
N1 C12 C13 N2 175.70(12) . . . . ?
C11 C12 C13 N2 -3.9(2) . . . . ?
N1 C12 C13 C14 -4.0(2) . . . . ?
C11 C12 C13 C14 176.38(14) . . . . ?
C14 C13 N2 C17 0.1(2) . . . . ?
C12 C13 N2 C17 -179.67(13) . . . . ?
N2 C13 C14 C15 -0.2(2) . . . . ?
C12 C13 C14 C15 179.48(14) . . . . ?
N1 C12 C11 C10 -0.5(2) . . . . ?
C13 C12 C11 C10 179.08(14) . . . . ?
C12 N1 C8 C9 0.3(2) . . . . ?
N1 C8 C9 C10 -0.8(3) . . . . ?
C13 N2 C17 C16 0.1(3) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
N2 C17 C16 C15 -0.2(3) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060874'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.3265(10)
_cell_length_b                   12.4430(11)
_cell_length_c                   21.1449(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2980.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29717
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3410
_reflns_number_gt                3073
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0439P)²+1.0985P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
H1O H 0.103(2) 0.1643(19) 0.3784(10) 0.059(7) Uiso 1 1 d . . . . .
H2O H -0.3098(19) 0.2709(17) 0.2038(10) 0.044(6) Uiso 1 1 d . . . . .
C1 C -0.02797(12) 0.18507(11) 0.32413(6) 0.0208(3) Uani 1 1 d . . . . .
C2 C -0.06147(13) 0.07737(11) 0.32516(7) 0.0245(3) Uani 1 1 d . . . . .
H2 H -0.0156 0.0260 0.3476 0.029 Uiso 1 1 calc R U . . .
C3 C -0.16242(13) 0.04597(12) 0.29315(7) 0.0270(3) Uani 1 1 d . . . . .
H3 H -0.1863 -0.0272 0.2940 0.032 Uiso 1 1 calc R U . . .
C4 C -0.22896(13) 0.12048(12) 0.25991(7) 0.0255(3) Uani 1 1 d . . . . .
H4 H -0.2985 0.0988 0.2383 0.031 Uiso 1 1 calc R U . . .
C5 C -0.19299(12) 0.22720(11) 0.25846(7) 0.0222(3) Uani 1 1 d . . . . .
C6 C -0.09293(12) 0.26241(11) 0.29117(7) 0.0211(3) Uani 1 1 d . . . . .
C7 C -0.05717(13) 0.37901(12) 0.29108(8) 0.0293(3) Uani 1 1 d . . . . .
H7A H -0.0844 0.4133 0.3302 0.044 Uiso 1 1 calc R U . . .
H7B H -0.0929 0.4153 0.2546 0.044 Uiso 1 1 calc R U . . .
H7C H 0.0290 0.3844 0.2884 0.044 Uiso 1 1 calc R U . . .
C8 C 0.16739(14) 0.06488(13) 0.48987(8) 0.0315(4) Uani 1 1 d . . . . .
H8 H 0.1108 0.1093 0.5103 0.038 Uiso 1 1 calc R U . . .
C9 C 0.23508(14) -0.00318(13) 0.52659(7) 0.0294(3) Uani 1 1 d . . . . .
H9 H 0.2249 -0.0044 0.5712 0.035 Uiso 1 1 calc R U . . .
C10 C 0.31849(12) -0.07021(11) 0.49814(7) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.32752(14) -0.06421(12) 0.43262(7) 0.0288(3) Uani 1 1 d . . . . .
H11 H 0.3819 -0.1088 0.4107 0.035 Uiso 1 1 calc R U . . .
C12 C 0.25713(15) 0.00692(14) 0.39969(8) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.2657 0.0103 0.3550 0.040 Uiso 1 1 calc R U . . .
C13 C 0.39460(13) -0.14392(12) 0.53534(7) 0.0250(3) Uani 1 1 d . . . . .
C14 C 0.35658(16) -0.18536(14) 0.59305(8) 0.0346(4) Uani 1 1 d . . . . .
H14 H 0.2802 -0.1677 0.6085 0.041 Uiso 1 1 calc R U . . .
C15 C 0.42962(18) -0.25254(16) 0.62833(8) 0.0420(4) Uani 1 1 d . . . . .
H15 H 0.4030 -0.2802 0.6677 0.050 Uiso 1 1 calc R U . . .
C16 C 0.54063(16) -0.27905(14) 0.60624(9) 0.0382(4) Uani 1 1 d . . . . .
H16 H 0.5907 -0.3242 0.6306 0.046 Uiso 1 1 calc R U . . .
C17 C 0.57868(15) -0.23974(13) 0.54851(9) 0.0351(4) Uani 1 1 d . . . . .
H17 H 0.6546 -0.2586 0.5330 0.042 Uiso 1 1 calc R U . . .
C18 C 0.50625(14) -0.17280(12) 0.51320(8) 0.0298(3) Uani 1 1 d . . . . .
H18 H 0.5329 -0.1464 0.4735 0.036 Uiso 1 1 calc R U . . .
N1 N 0.17740(12) 0.07146(10) 0.42696(6) 0.0309(3) Uani 1 1 d . . . . .
O1 O 0.07229(9) 0.21955(8) 0.35461(5) 0.0243(2) Uani 1 1 d . . . . .
O2 O -0.25576(10) 0.30367(9) 0.22579(5) 0.0276(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 O1 1.3745(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.3975(19) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 O2 1.3742(17) . ?
C5 C6 1.398(2) . ?
C6 C7 1.5064(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.338(2) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 C13 1.484(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 N1 1.339(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 C18 1.395(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1 H1O 0.92(2) . ?
O2 H2O 0.87(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
O1 C1 C2 121.20(12) . . ?
O1 C1 C6 116.99(12) . . ?
C2 C1 C6 121.80(13) . . ?
C3 C2 C1 119.25(13) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.54(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.40(13) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O2 C5 C4 121.41(13) . . ?
O2 C5 C6 116.82(12) . . ?
C4 C5 C6 121.76(13) . . ?
C1 C6 C5 117.23(13) . . ?
C1 C6 C7 121.49(13) . . ?
C5 C6 C7 121.27(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 123.33(15) . . ?
N1 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C8 C9 C10 119.97(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 116.54(13) . . ?
C11 C10 C13 121.21(13) . . ?
C9 C10 C13 122.25(13) . . ?
C12 C11 C10 119.63(14) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N1 C12 C11 123.85(15) . . ?
N1 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C14 C13 C18 118.60(14) . . ?
C14 C13 C10 120.89(14) . . ?
C18 C13 C10 120.50(14) . . ?
C15 C14 C13 120.52(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.19(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.83(15) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.19(16) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.66(15) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C8 N1 C12 116.67(13) . . ?
C1 O1 H1O 109.7(14) . . ?
C5 O2 H2O 108.0(14) . . ?

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 -179.23(13) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 O2 179.58(13) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
O1 C1 C6 C5 178.08(12) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
O1 C1 C6 C7 -2.2(2) . . . . ?
C2 C1 C6 C7 179.06(14) . . . . ?
O2 C5 C6 C1 -179.50(12) . . . . ?
C4 C5 C6 C1 1.8(2) . . . . ?
O2 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C6 C7 -177.87(14) . . . . ?
N1 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 C13 179.24(14) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C13 C10 C11 C12 -178.59(14) . . . . ?
C10 C11 C12 N1 -0.9(3) . . . . ?
C11 C10 C13 C14 -152.15(16) . . . . ?
C9 C10 C13 C14 28.2(2) . . . . ?
C11 C10 C13 C18 28.1(2) . . . . ?
C9 C10 C13 C18 -151.52(15) . . . . ?
C18 C13 C14 C15 1.2(3) . . . . ?
C10 C13 C14 C15 -178.55(16) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
C10 C13 C18 C17 178.55(14) . . . . ?
C9 C8 N1 C12 0.7(2) . . . . ?
C11 C12 N1 C8 0.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O1 0.95 2.50 3.3538(19) 150.1 8_655
O2 H2O O1 0.87(2) 1.93(2) 2.7890(15) 170(2) 6_556

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060875'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34

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                   7.900(4)
_cell_length_b                   22.159(11)
_cell_length_c                   8.964(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.540(5)
_cell_angle_gamma                90
_cell_volume                     1504.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15128
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3448
_reflns_number_gt                3084
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0773P)²+0.2381P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3448
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
H2O H -0.121(3) 0.3103(10) 0.280(2) 0.055(6) Uiso 1 1 d . . . . .
H1O H 0.182(3) 0.1084(10) 0.746(2) 0.053(6) Uiso 1 1 d . . . . .
O1 O 0.20993(11) 0.13411(4) 0.68515(11) 0.0258(2) Uani 1 1 d . . . . .
O2 O -0.02956(12) 0.28330(4) 0.31097(11) 0.0295(2) Uani 1 1 d . . . . .
N1 N 0.10586(14) 0.03409(5) 0.81263(12) 0.0256(3) Uani 1 1 d . . . . .
C18 C 0.32132(16) 0.03230(6) 1.06619(14) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.17905(17) -0.06211(6) 0.94381(16) 0.0271(3) Uani 1 1 d . . . . .
C1 C 0.08648(15) 0.20716(5) 0.49296(14) 0.0213(3) Uani 1 1 d . . . . .
N2 N 0.33626(15) 0.09317(5) 1.05789(13) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.06744(15) 0.16959(5) 0.61187(13) 0.0212(3) Uani 1 1 d . . . . .
C3 C -0.08613(16) 0.16912(6) 0.65879(15) 0.0251(3) Uani 1 1 d . . . . .
H3 H -0.0962 0.1431 0.7401 0.030 Uiso 1 1 calc R U . . .
C19 C 0.19836(16) 0.00124(5) 0.93736(14) 0.0233(3) Uani 1 1 d . . . . .
C13 C 0.39898(19) -0.06642(7) 1.19502(17) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.4669 -0.0892 1.2811 0.040 Uiso 1 1 calc R U . . .
C6 C -0.05418(16) 0.24573(5) 0.42370(14) 0.0222(3) Uani 1 1 d . . . . .
C5 C -0.21018(16) 0.24554(6) 0.46734(15) 0.0262(3) Uani 1 1 d . . . . .
H5 H -0.3054 0.2713 0.4169 0.031 Uiso 1 1 calc R U . . .
C15 C 0.53839(19) 0.02893(7) 1.31777(16) 0.0340(3) Uani 1 1 d . . . . .
H15 H 0.6072 0.0075 1.4061 0.041 Uiso 1 1 calc R U . . .
C10 C 0.05759(19) -0.09064(6) 0.81771(18) 0.0333(3) Uani 1 1 d . . . . .
H10 H 0.0419 -0.1331 0.8183 0.040 Uiso 1 1 calc R U . . .
C12 C 0.28423(19) -0.09507(6) 1.07506(17) 0.0325(3) Uani 1 1 d . . . . .
H12 H 0.2732 -0.1377 1.0778 0.039 Uiso 1 1 calc R U . . .
C9 C -0.03808(19) -0.05696(7) 0.69402(17) 0.0340(3) Uani 1 1 d . . . . .
H9 H -0.1222 -0.0753 0.6087 0.041 Uiso 1 1 calc R U . . .
C7 C 0.25130(17) 0.20761(6) 0.44025(16) 0.0273(3) Uani 1 1 d . . . . .
H7A H 0.3184 0.2446 0.4770 0.041 Uiso 1 1 calc R U . . .
H7B H 0.2188 0.2062 0.3263 0.041 Uiso 1 1 calc R U . . .
H7C H 0.3239 0.1724 0.4831 0.041 Uiso 1 1 calc R U . . .
C14 C 0.41972(17) -0.00230(6) 1.19434(15) 0.0277(3) Uani 1 1 d . . . . .
C17 C 0.4496(2) 0.12025(7) 1.17694(16) 0.0337(3) Uani 1 1 d . . . . .
H17 H 0.4612 0.1628 1.1724 0.040 Uiso 1 1 calc R U . . .
C4 C -0.22422(16) 0.20715(6) 0.58533(15) 0.0268(3) Uani 1 1 d . . . . .
H4 H -0.3297 0.2069 0.6163 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5538(2) 0.09015(7) 1.30949(16) 0.0365(3) Uani 1 1 d . . . . .
H16 H 0.6331 0.1119 1.3914 0.044 Uiso 1 1 calc R U . . .
C8 C -0.00801(18) 0.00538(6) 0.69726(16) 0.0303(3) Uani 1 1 d . . . . .
H8 H -0.0736 0.0286 0.6110 0.036 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 C2 1.3769(15) . ?
O1 H1O 0.86(2) . ?
O2 C6 1.3652(16) . ?
O2 H2O 0.92(2) . ?
N1 C8 1.3243(17) . ?
N1 C19 1.3598(16) . ?
C18 N2 1.3577(18) . ?
C18 C14 1.4154(18) . ?
C18 C19 1.4534(18) . ?
C11 C10 1.407(2) . ?
C11 C19 1.4151(19) . ?
C11 C12 1.4322(19) . ?
C1 C2 1.3939(18) . ?
C1 C6 1.3992(17) . ?
C1 C7 1.5063(18) . ?
N2 C17 1.3253(18) . ?
C2 C3 1.3926(18) . ?
C3 C4 1.3873(19) . ?
C3 H3 0.9500 . ?
C13 C12 1.351(2) . ?
C13 C14 1.430(2) . ?
C13 H13 0.9500 . ?
C6 C5 1.3951(19) . ?
C5 C4 1.3862(19) . ?
C5 H5 0.9500 . ?
C15 C16 1.366(2) . ?
C15 C14 1.411(2) . ?
C15 H15 0.9500 . ?
C10 C9 1.371(2) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C9 C8 1.400(2) . ?
C9 H9 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C17 C16 1.406(2) . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1O 110.9(14) . . ?
C6 O2 H2O 111.0(13) . . ?
C8 N1 C19 118.12(12) . . ?
N2 C18 C14 123.12(12) . . ?
N2 C18 C19 118.41(11) . . ?
C14 C18 C19 118.47(13) . . ?
C10 C11 C19 118.00(12) . . ?
C10 C11 C12 122.29(13) . . ?
C19 C11 C12 119.70(12) . . ?
C2 C1 C6 117.33(11) . . ?
C2 C1 C7 122.34(11) . . ?
C6 C1 C7 120.32(11) . . ?
C17 N2 C18 117.07(12) . . ?
O1 C2 C3 121.05(11) . . ?
O1 C2 C1 117.02(11) . . ?
C3 C2 C1 121.90(11) . . ?
C4 C3 C2 119.14(12) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N1 C19 C11 121.72(12) . . ?
N1 C19 C18 118.74(12) . . ?
C11 C19 C18 119.53(11) . . ?
C12 C13 C14 121.00(12) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
O2 C6 C5 122.19(11) . . ?
O2 C6 C1 116.01(11) . . ?
C5 C6 C1 121.81(12) . . ?
C4 C5 C6 118.99(11) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C16 C15 C14 119.60(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C9 C10 C11 119.86(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C13 C12 C11 120.99(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C10 C9 C8 117.96(13) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C14 C18 117.36(13) . . ?
C15 C14 C13 122.35(12) . . ?
C18 C14 C13 120.29(12) . . ?
N2 C17 C16 124.36(14) . . ?
N2 C17 H17 117.8 . . ?
C16 C17 H17 117.8 . . ?
C5 C4 C3 120.80(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C15 C16 C17 118.50(14) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N1 C8 C9 124.31(13) . . ?
N1 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?

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
C14 C18 N2 C17 0.13(18) . . . . ?
C19 C18 N2 C17 -179.91(11) . . . . ?
C6 C1 C2 O1 -176.61(10) . . . . ?
C7 C1 C2 O1 2.68(17) . . . . ?
C6 C1 C2 C3 1.30(17) . . . . ?
C7 C1 C2 C3 -179.41(11) . . . . ?
O1 C2 C3 C4 177.76(10) . . . . ?
C1 C2 C3 C4 -0.07(18) . . . . ?
C8 N1 C19 C11 1.81(18) . . . . ?
C8 N1 C19 C18 -178.84(11) . . . . ?
C10 C11 C19 N1 -1.25(18) . . . . ?
C12 C11 C19 N1 177.65(12) . . . . ?
C10 C11 C19 C18 179.40(11) . . . . ?
C12 C11 C19 C18 -1.70(17) . . . . ?
N2 C18 C19 N1 1.24(17) . . . . ?
C14 C18 C19 N1 -178.79(10) . . . . ?
N2 C18 C19 C11 -179.39(11) . . . . ?
C14 C18 C19 C11 0.57(17) . . . . ?
C2 C1 C6 O2 178.04(10) . . . . ?
C7 C1 C6 O2 -1.27(16) . . . . ?
C2 C1 C6 C5 -2.12(17) . . . . ?
C7 C1 C6 C5 178.58(11) . . . . ?
O2 C6 C5 C4 -178.49(11) . . . . ?
C1 C6 C5 C4 1.68(18) . . . . ?
C19 C11 C10 C9 -0.27(19) . . . . ?
C12 C11 C10 C9 -179.14(12) . . . . ?
C14 C13 C12 C11 -0.3(2) . . . . ?
C10 C11 C12 C13 -179.55(12) . . . . ?
C19 C11 C12 C13 1.6(2) . . . . ?
C11 C10 C9 C8 1.1(2) . . . . ?
C16 C15 C14 C18 0.03(19) . . . . ?
C16 C15 C14 C13 179.23(13) . . . . ?
N2 C18 C14 C15 -0.14(19) . . . . ?
C19 C18 C14 C15 179.90(11) . . . . ?
N2 C18 C14 C13 -179.35(12) . . . . ?
C19 C18 C14 C13 0.68(18) . . . . ?
C12 C13 C14 C15 180.00(13) . . . . ?
C12 C13 C14 C18 -0.82(19) . . . . ?
C18 N2 C17 C16 0.0(2) . . . . ?
C6 C5 C4 C3 -0.37(19) . . . . ?
C2 C3 C4 C5 -0.42(18) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
N2 C17 C16 C15 -0.1(2) . . . . ?
C19 N1 C8 C9 -0.9(2) . . . . ?
C10 C9 C8 N1 -0.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.86(2) 1.90(2) 2.7255(17) 158(2) .

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060876'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35

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'
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                   7.842(2)
_cell_length_b                   21.894(4)
_cell_length_c                   9.260(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.278(12)
_cell_angle_gamma                90
_cell_volume                     1526.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14215
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_av_R_equivalents  0.1641
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3002
_reflns_number_gt                2618
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0841P)²+0.3555P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3002
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
H2O H 0.617(4) 0.3010(15) 1.226(3) 0.056(9) Uiso 1 1 d . . . . .
H1O H 0.312(4) 0.1102(17) 0.760(4) 0.074(10) Uiso 1 1 d . . . . .
O1 O 0.29483(18) 0.13584(7) 0.81512(17) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.5369(2) 0.27861(7) 1.19639(17) 0.0359(4) Uani 1 1 d . . . . .
C1 C 0.4181(2) 0.20667(8) 1.0080(2) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.4387(2) 0.17073(8) 0.8892(2) 0.0262(4) Uani 1 1 d . . . . .
C5 C 0.7190(3) 0.24420(9) 1.0396(2) 0.0308(5) Uani 1 1 d . . . . .
H5 H 0.8158 0.2689 1.0928 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5935(3) 0.17139(9) 0.8449(2) 0.0313(5) Uani 1 1 d . . . . .
H3 H 0.6036 0.1468 0.7632 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5604(2) 0.24367(8) 1.0805(2) 0.0267(4) Uani 1 1 d . . . . .
C7 C 0.2508(3) 0.20587(10) 1.0572(2) 0.0328(5) Uani 1 1 d . . . . .
H7A H 0.2816 0.2062 1.1673 0.049 Uiso 1 1 calc R U . . .
H7B H 0.1826 0.1689 1.0189 0.049 Uiso 1 1 calc R U . . .
H7C H 0.1792 0.2420 1.0175 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7329(3) 0.20820(9) 0.9206(2) 0.0328(5) Uani 1 1 d . . . . .
H4 H 0.8394 0.2088 0.8908 0.039 Uiso 1 1 calc R U . . .
N1 N 0.3883(2) 0.03489(8) 0.68324(19) 0.0328(4) Uani 1 1 d . . . . .
C20 C 0.1814(3) 0.03015(9) 0.4339(2) 0.0301(5) Uani 1 1 d . . . . .
C12 C 0.3203(3) -0.06382(9) 0.5637(2) 0.0328(5) Uani 1 1 d . . . . .
C8 C 0.3002(3) 0.00031(9) 0.5634(2) 0.0290(5) Uani 1 1 d . . . . .
C16 C -0.0288(3) 0.02223(12) 0.1847(3) 0.0435(6) Uani 1 1 d . . . . .
H16 H -0.0922 -0.0021 0.1021 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4374(3) -0.09109(10) 0.6899(3) 0.0404(5) Uani 1 1 d . . . . .
H11 H 0.4522 -0.1342 0.6939 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1103(3) -0.07108(11) 0.3177(2) 0.0396(5) Uani 1 1 d . . . . .
H14 H 0.0461 -0.0954 0.2354 0.048 Uiso 1 1 calc R U . . .
C18 C 0.0416(3) 0.12008(11) 0.2993(2) 0.0418(5) Uani 1 1 d . . . . .
H18 H 0.0257 0.1631 0.2950 0.050 Uiso 1 1 calc R U . . .
C15 C 0.0873(3) -0.00604(10) 0.3111(2) 0.0348(5) Uani 1 1 d . . . . .
C13 C 0.2202(3) -0.09835(10) 0.4373(2) 0.0379(5) Uani 1 1 d . . . . .
H13 H 0.2320 -0.1415 0.4382 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5301(3) -0.05570(11) 0.8073(3) 0.0413(5) Uani 1 1 d . . . . .
H10 H 0.6130 -0.0734 0.8920 0.050 Uiso 1 1 calc R U . . .
C19 C 0.1566(3) 0.09393(10) 0.4241(2) 0.0352(5) Uani 1 1 d . . . . .
H19 H 0.2200 0.1192 0.5047 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4996(3) 0.00735(10) 0.7993(2) 0.0378(5) Uani 1 1 d . . . . .
H9 H 0.5623 0.0318 0.8819 0.045 Uiso 1 1 calc R U . . .
C17 C -0.0514(3) 0.08414(13) 0.1794(3) 0.0464(6) Uani 1 1 d . . . . .
H17 H -0.1306 0.1026 0.0937 0.056 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 C2 1.376(2) . ?
O1 H1O 0.80(4) . ?
O2 C6 1.372(2) . ?
O2 H2O 0.78(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.398(3) . ?
C1 C7 1.505(3) . ?
C2 C3 1.386(3) . ?
C5 C4 1.384(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 H4 0.9500 . ?
N1 C9 1.325(3) . ?
N1 C8 1.361(3) . ?
C20 C19 1.409(3) . ?
C20 C15 1.412(3) . ?
C20 C8 1.452(3) . ?
C12 C11 1.401(3) . ?
C12 C8 1.413(3) . ?
C12 C13 1.429(3) . ?
C16 C17 1.366(4) . ?
C16 C15 1.409(3) . ?
C16 H16 0.9500 . ?
C11 C10 1.367(3) . ?
C11 H11 0.9500 . ?
C14 C13 1.338(3) . ?
C14 C15 1.435(3) . ?
C14 H14 0.9500 . ?
C18 C19 1.376(3) . ?
C18 C17 1.389(3) . ?
C18 H18 0.9500 . ?
C13 H13 0.9500 . ?
C10 C9 1.399(3) . ?
C10 H10 0.9500 . ?
C19 H19 0.9500 . ?
C9 H9 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1O 117(2) . . ?
C6 O2 H2O 111(2) . . ?
C6 C1 C2 116.99(17) . . ?
C6 C1 C7 120.70(16) . . ?
C2 C1 C7 122.31(17) . . ?
O1 C2 C3 121.45(17) . . ?
O1 C2 C1 116.45(16) . . ?
C3 C2 C1 122.08(17) . . ?
C4 C5 C6 119.08(18) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C4 C3 C2 119.34(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O2 C6 C1 115.92(17) . . ?
O2 C6 C5 122.15(17) . . ?
C1 C6 C5 121.92(17) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C5 120.57(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C9 N1 C8 118.48(18) . . ?
C19 C20 C15 118.20(19) . . ?
C19 C20 C8 122.96(19) . . ?
C15 C20 C8 118.83(19) . . ?
C11 C12 C8 118.17(19) . . ?
C11 C12 C13 122.6(2) . . ?
C8 C12 C13 119.24(19) . . ?
N1 C8 C12 121.34(18) . . ?
N1 C8 C20 119.01(18) . . ?
C12 C8 C20 119.64(18) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C14 C15 121.49(19) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C15 C20 119.5(2) . . ?
C16 C15 C14 121.1(2) . . ?
C20 C15 C14 119.42(19) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C18 C19 C20 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
N1 C9 C10 123.8(2) . . ?
N1 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -177.92(15) . . . . ?
C7 C1 C2 O1 2.3(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C7 C1 C2 C3 -179.64(17) . . . . ?
O1 C2 C3 C4 178.55(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C1 C6 O2 179.84(16) . . . . ?
C7 C1 C6 O2 -0.3(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C7 C1 C6 C5 178.39(18) . . . . ?
C4 C5 C6 O2 -179.41(18) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C6 C5 C4 C3 -1.2(3) . . . . ?
C9 N1 C8 C12 2.6(3) . . . . ?
C9 N1 C8 C20 -178.42(17) . . . . ?
C11 C12 C8 N1 -1.6(3) . . . . ?
C13 C12 C8 N1 177.82(18) . . . . ?
C11 C12 C8 C20 179.41(18) . . . . ?
C13 C12 C8 C20 -1.2(3) . . . . ?
C19 C20 C8 N1 2.0(3) . . . . ?
C15 C20 C8 N1 -178.61(17) . . . . ?
C19 C20 C8 C12 -178.93(18) . . . . ?
C15 C20 C8 C12 0.4(3) . . . . ?
C8 C12 C11 C10 -0.9(3) . . . . ?
C13 C12 C11 C10 179.7(2) . . . . ?
C17 C16 C15 C20 0.0(3) . . . . ?
C17 C16 C15 C14 179.5(2) . . . . ?
C19 C20 C15 C16 -0.7(3) . . . . ?
C8 C20 C15 C16 179.90(17) . . . . ?
C19 C20 C15 C14 179.83(18) . . . . ?
C8 C20 C15 C14 0.5(3) . . . . ?
C13 C14 C15 C16 -180.0(2) . . . . ?
C13 C14 C15 C20 -0.6(3) . . . . ?
C15 C14 C13 C12 -0.2(3) . . . . ?
C11 C12 C13 C14 -179.50(19) . . . . ?
C8 C12 C13 C14 1.1(3) . . . . ?
C12 C11 C10 C9 2.2(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C15 C20 C19 C18 1.0(3) . . . . ?
C8 C20 C19 C18 -179.64(18) . . . . ?
C8 N1 C9 C10 -1.1(3) . . . . ?
C11 C10 C9 N1 -1.3(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C19 C18 C17 C16 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.80(4) 1.95(4) 2.723(2) 162(3) .

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060877'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O2'
_chemical_formula_weight         218.25

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                   7.986(5)
_cell_length_b                   16.748(10)
_cell_length_c                   8.276(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.474(8)
_cell_angle_gamma                90
_cell_volume                     1106.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11480
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.432
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2534
_reflns_number_gt                2264
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0870P)²+0.1758P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
H2N H 0.160(3) 0.4895(14) 0.795(3) 0.049(6) Uiso 1 1 d . . . . .
H1N H 0.241(3) 0.4062(14) 0.763(2) 0.046(5) Uiso 1 1 d . . . . .
H1O H 0.442(3) 0.3193(13) 0.898(3) 0.051(6) Uiso 1 1 d . . . . .
H2O H 0.139(4) 0.0829(19) 0.380(4) 0.097(10) Uiso 1 1 d . . . . .
O2 O 0.10221(12) 0.11991(6) 0.48315(11) 0.0270(3) Uani 1 1 d . . . . .
O1 O 0.34613(13) 0.30485(6) 0.84643(13) 0.0315(3) Uani 1 1 d . . . . .
C3 C 0.52538(17) 0.20733(9) 0.71967(17) 0.0294(3) Uani 1 1 d . . . . .
H3 H 0.6216 0.2276 0.7741 0.035 Uiso 1 1 calc R U . . .
C6 C 0.24086(16) 0.14799(8) 0.55999(15) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.33407(15) 0.53793(7) 0.26841(15) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.22398(16) 0.21232(8) 0.66764(16) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.36789(17) 0.24149(8) 0.74454(16) 0.0249(3) Uani 1 1 d . . . . .
C4 C 0.53862(17) 0.14353(9) 0.61451(17) 0.0309(3) Uani 1 1 d . . . . .
H4 H 0.6451 0.1200 0.5966 0.037 Uiso 1 1 calc R U . . .
C10 C 0.24345(16) 0.48060(8) 0.57361(16) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.05536(17) 0.24924(9) 0.7001(2) 0.0331(4) Uani 1 1 d . . . . .
H7A H 0.0398 0.2961 0.6308 0.050 Uiso 1 1 calc R U . . .
H7B H 0.0496 0.2654 0.8137 0.050 Uiso 1 1 calc R U . . .
H7C H -0.0330 0.2102 0.6769 0.050 Uiso 1 1 calc R U . . .
N2 N 0.20163(18) 0.45446(8) 0.72249(16) 0.0345(3) Uani 1 1 d . . . . .
C5 C 0.39855(17) 0.11323(9) 0.53454(16) 0.0275(3) Uani 1 1 d . . . . .
H5 H 0.4095 0.0692 0.4630 0.033 Uiso 1 1 calc R U . . .
C8 C 0.37229(17) 0.46306(8) 0.31454(17) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.4316 0.4300 0.2414 0.034 Uiso 1 1 calc R U . . .
C11 C 0.20192(18) 0.55857(8) 0.52363(17) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.1418 0.5932 0.5931 0.035 Uiso 1 1 calc R U . . .
C9 C 0.32959(17) 0.43211(8) 0.46241(17) 0.0267(3) Uani 1 1 d . . . . .
H9 H 0.3578 0.3786 0.4894 0.032 Uiso 1 1 calc R U . . .
C12 C 0.24946(19) 0.58364(8) 0.37367(18) 0.0315(3) Uani 1 1 d . . . . .
H12 H 0.2211 0.6365 0.3419 0.038 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
O2 C6 1.3564(17) . ?
O2 H2O 1.10(3) . ?
O1 C2 1.3674(18) . ?
O1 H1O 0.91(2) . ?
C3 C4 1.383(2) . ?
C3 C2 1.398(2) . ?
C3 H3 0.9500 . ?
C6 C5 1.4047(19) . ?
C6 C1 1.4052(19) . ?
N1 C8 1.3452(19) . ?
N1 C12 1.3458(19) . ?
C1 C2 1.3972(19) . ?
C1 C7 1.5079(19) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C10 N2 1.352(2) . ?
C10 C11 1.408(2) . ?
C10 C9 1.411(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N2 H2N 0.90(2) . ?
N2 H1N 0.93(2) . ?
C5 H5 0.9500 . ?
C8 C9 1.374(2) . ?
C8 H8 0.9500 . ?
C11 C12 1.367(2) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2O 109.8(16) . . ?
C2 O1 H1O 112.6(14) . . ?
C4 C3 C2 118.84(13) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
O2 C6 C5 121.02(12) . . ?
O2 C6 C1 118.74(12) . . ?
C5 C6 C1 120.24(12) . . ?
C8 N1 C12 117.42(13) . . ?
C2 C1 C6 118.29(12) . . ?
C2 C1 C7 120.52(13) . . ?
C6 C1 C7 121.19(12) . . ?
O1 C2 C1 116.36(12) . . ?
O1 C2 C3 121.83(12) . . ?
C1 C2 C3 121.81(13) . . ?
C3 C4 C5 121.07(13) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N2 C10 C11 120.56(13) . . ?
N2 C10 C9 122.24(13) . . ?
C11 C10 C9 117.19(13) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 N2 H2N 119.2(14) . . ?
C10 N2 H1N 121.7(13) . . ?
H2N N2 H1N 116.9(19) . . ?
C4 C5 C6 119.73(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C8 C9 123.15(13) . . ?
N1 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C12 C11 C10 119.01(13) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C8 C9 C10 119.32(13) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N1 C12 C11 123.89(13) . . ?
N1 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C1 C2 -179.15(11) . . . . ?
C5 C6 C1 C2 1.53(19) . . . . ?
O2 C6 C1 C7 0.87(19) . . . . ?
C5 C6 C1 C7 -178.44(12) . . . . ?
C6 C1 C2 O1 179.07(11) . . . . ?
C7 C1 C2 O1 -0.96(19) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C7 C1 C2 C3 178.53(13) . . . . ?
C4 C3 C2 O1 -179.77(12) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
O2 C6 C5 C4 179.73(12) . . . . ?
C1 C6 C5 C4 -1.0(2) . . . . ?
C12 N1 C8 C9 -0.2(2) . . . . ?
N2 C10 C11 C12 178.54(14) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
N1 C8 C9 C10 -0.9(2) . . . . ?
N2 C10 C9 C8 -178.28(13) . . . . ?
C11 C10 C9 C8 1.64(19) . . . . ?
C8 N1 C12 C11 0.5(2) . . . . ?
C10 C11 C12 N1 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1 0.93(2) 2.01(2) 2.940(2) 175(2) .

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060878'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30

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                   7.718(5)
_cell_length_b                   18.754(11)
_cell_length_c                   9.201(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.278(8)
_cell_angle_gamma                90
_cell_volume                     1323.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12859
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3027
_reflns_number_gt                2687
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0702P)²+0.2263P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
H2O H 0.953(3) 0.2105(12) 0.935(2) 0.059(6) Uiso 1 1 d . . . . .
H1O H 0.644(4) 0.3926(14) 0.404(3) 0.088(8) Uiso 1 1 d . . . . .
O2 O 0.86070(15) 0.23867(6) 0.90851(11) 0.0406(3) Uani 1 1 d . . . . .
O1 O 0.61120(13) 0.36123(5) 0.48912(11) 0.0354(3) Uani 1 1 d . . . . .
C6 C 0.88567(18) 0.27447(7) 0.78320(14) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.73638(17) 0.30148(6) 0.70136(13) 0.0274(3) Uani 1 1 d . . . . .
N1 N 1.32263(19) 0.56900(7) -0.25478(15) 0.0438(3) Uani 1 1 d . . . . .
C2 C 0.75877(18) 0.33705(6) 0.57111(14) 0.0287(3) Uani 1 1 d . . . . .
C10 C 1.24960(17) 0.49315(7) -0.00263(14) 0.0314(3) Uani 1 1 d . . . . .
N2 N 1.21811(19) 0.45650(7) 0.11848(14) 0.0400(3) Uani 1 1 d . . . . .
C3 C 0.9237(2) 0.34675(8) 0.52618(15) 0.0355(3) Uani 1 1 d . . . . .
H3 H 0.9367 0.3713 0.4377 0.043 Uiso 1 1 calc R U . . .
C9 C 1.2821(2) 0.45833(8) -0.13286(16) 0.0393(4) Uani 1 1 d . . . . .
H9 H 1.2796 0.4077 -0.1383 0.047 Uiso 1 1 calc R U . . .
C4 C 1.06853(19) 0.32040(8) 0.61113(16) 0.0368(3) Uani 1 1 d . . . . .
H4 H 1.1811 0.3274 0.5809 0.044 Uiso 1 1 calc R U . . .
C5 C 1.05144(18) 0.28396(7) 0.73956(15) 0.0333(3) Uani 1 1 d . . . . .
H5 H 1.1513 0.2657 0.7971 0.040 Uiso 1 1 calc R U . . .
C11 C 1.2516(2) 0.56832(8) -0.00715(16) 0.0386(4) Uani 1 1 d . . . . .
H11 H 1.2278 0.5952 0.0759 0.046 Uiso 1 1 calc R U . . .
C7 C 0.55813(18) 0.29248(8) 0.75175(15) 0.0337(3) Uani 1 1 d . . . . .
H7A H 0.4888 0.3355 0.7280 0.051 Uiso 1 1 calc R U . . .
H7B H 0.5700 0.2847 0.8577 0.051 Uiso 1 1 calc R U . . .
H7C H 0.4998 0.2513 0.7023 0.051 Uiso 1 1 calc R U . . .
C13 C 1.2174(3) 0.37918(8) 0.1191(2) 0.0495(4) Uani 1 1 d . . . . .
H13A H 1.1249 0.3618 0.0463 0.074 Uiso 1 1 calc R U . . .
H13B H 1.1965 0.3620 0.2162 0.074 Uiso 1 1 calc R U . . .
H13C H 1.3304 0.3615 0.0951 0.074 Uiso 1 1 calc R U . . .
C12 C 1.2883(2) 0.60228(8) -0.13203(18) 0.0447(4) Uani 1 1 d . . . . .
H12 H 1.2894 0.6529 -0.1317 0.054 Uiso 1 1 calc R U . . .
C8 C 1.3171(2) 0.49777(9) -0.25148(17) 0.0438(4) Uani 1 1 d . . . . .
H8 H 1.3390 0.4728 -0.3374 0.053 Uiso 1 1 calc R U . . .
C14 C 1.1916(3) 0.49318(10) 0.25336(18) 0.0515(4) Uani 1 1 d . . . . .
H14A H 1.2945 0.5221 0.2854 0.077 Uiso 1 1 calc R U . . .
H14B H 1.1733 0.4581 0.3291 0.077 Uiso 1 1 calc R U . . .
H14C H 1.0890 0.5241 0.2367 0.077 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
O2 C6 1.3660(18) . ?
O2 H2O 0.90(2) . ?
O1 C2 1.3726(18) . ?
O1 H1O 1.04(3) . ?
C6 C5 1.394(2) . ?
C6 C1 1.401(2) . ?
C1 C2 1.3988(19) . ?
C1 C7 1.508(2) . ?
N1 C8 1.337(2) . ?
N1 C12 1.342(2) . ?
C2 C3 1.393(2) . ?
C10 N2 1.3537(19) . ?
C10 C11 1.410(2) . ?
C10 C9 1.411(2) . ?
N2 C13 1.450(2) . ?
N2 C14 1.453(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C9 C8 1.370(2) . ?
C9 H9 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C11 C12 1.370(2) . ?
C11 H11 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2O 109.7(14) . . ?
C2 O1 H1O 110.5(15) . . ?
O2 C6 C5 121.65(12) . . ?
O2 C6 C1 116.61(12) . . ?
C5 C6 C1 121.74(13) . . ?
C2 C1 C6 117.50(12) . . ?
C2 C1 C7 121.26(12) . . ?
C6 C1 C7 121.23(12) . . ?
C8 N1 C12 115.83(13) . . ?
O1 C2 C3 121.61(13) . . ?
O1 C2 C1 117.10(12) . . ?
C3 C2 C1 121.28(12) . . ?
N2 C10 C11 122.36(13) . . ?
N2 C10 C9 121.92(14) . . ?
C11 C10 C9 115.71(13) . . ?
C10 N2 C13 120.78(13) . . ?
C10 N2 C14 121.17(14) . . ?
C13 N2 C14 118.00(13) . . ?
C4 C3 C2 119.60(13) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C8 C9 C10 119.72(14) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C3 C4 C5 120.82(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.04(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C12 C11 C10 119.56(14) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C12 C11 124.59(14) . . ?
N1 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
N1 C8 C9 124.55(15) . . ?
N1 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C1 C2 -178.73(11) . . . . ?
C5 C6 C1 C2 1.64(18) . . . . ?
O2 C6 C1 C7 1.22(17) . . . . ?
C5 C6 C1 C7 -178.41(12) . . . . ?
C6 C1 C2 O1 177.85(11) . . . . ?
C7 C1 C2 O1 -2.10(17) . . . . ?
C6 C1 C2 C3 -1.49(18) . . . . ?
C7 C1 C2 C3 178.56(12) . . . . ?
C11 C10 N2 C13 -179.88(15) . . . . ?
C9 C10 N2 C13 0.3(2) . . . . ?
C11 C10 N2 C14 -2.6(2) . . . . ?
C9 C10 N2 C14 177.61(15) . . . . ?
O1 C2 C3 C4 -178.89(12) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
N2 C10 C9 C8 -178.53(14) . . . . ?
C11 C10 C9 C8 1.6(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
O2 C6 C5 C4 179.68(12) . . . . ?
C1 C6 C5 C4 -0.70(19) . . . . ?
N2 C10 C11 C12 178.52(14) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
C8 N1 C12 C11 1.0(2) . . . . ?
C10 C11 C12 N1 0.4(3) . . . . ?
C12 N1 C8 C9 -1.0(3) . . . . ?
C10 C9 C8 N1 -0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 1.04(3) 1.59(3) 2.620(2) 170(2) 3_765

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060879'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   20.478(4)
_cell_length_b                   7.1225(13)
_cell_length_c                   12.930(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.578(9)
_cell_angle_gamma                90
_cell_volume                     1880.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9645
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4273
_reflns_number_gt                3832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.986

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1147P)²+0.0556P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4273
_refine_ls_number_parameters     268
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1793
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
H1O H 0.061(4) 0.258(13) 0.372(6) 0.07(2) Uiso 1 1 d . . . . .
H2O H -0.008(3) 0.492(8) 0.806(5) 0.032(13) Uiso 1 1 d . . . . .
H4O H -0.264(4) -0.307(9) 0.972(5) 0.048(17) Uiso 1 1 d . . . . .
O1 O 0.03026(16) 0.3210(5) 0.4101(2) 0.0322(7) Uani 1 1 d . . . . .
N1 N 0.18327(18) -0.1642(5) 0.5908(3) 0.0322(8) Uani 1 1 d . . . . .
N2 N 0.11133(19) -0.1522(5) 0.7680(3) 0.0313(8) Uani 1 1 d . . . . .
C1 C 0.0027(2) 0.3790(5) 0.5817(3) 0.0252(8) Uani 1 1 d . . . . .
C2 C 0.0509(2) 0.3401(5) 0.5138(3) 0.0267(8) Uani 1 1 d . . . . .
C22 C 0.1163(2) -0.1506(5) 0.5813(3) 0.0262(8) Uani 1 1 d . . . . .
C6 C 0.02347(19) 0.4001(5) 0.6865(3) 0.0250(8) Uani 1 1 d . . . . .
C17 C 0.0805(2) -0.1415(6) 0.6703(3) 0.0254(8) Uani 1 1 d . . . . .
C5 C 0.0895(2) 0.3845(6) 0.7238(3) 0.0291(8) Uani 1 1 d . . . . .
H5 H 0.1024 0.4010 0.7954 0.035 Uiso 1 1 calc R U . . .
O3 O -0.11242(18) 0.1260(5) 0.7416(3) 0.0424(8) Uani 1 1 d . . . . .
H3O H -0.0956 0.2335 0.7469 0.064 Uiso 1 1 calc R U . . .
O4 O -0.23673(18) -0.2993(5) 0.9250(3) 0.0418(8) Uani 1 1 d . . . . .
C3 C 0.1169(2) 0.3226(6) 0.5489(4) 0.0315(9) Uani 1 1 d . . . . .
H3 H 0.1486 0.2958 0.5012 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0827(2) -0.1430(6) 0.4813(3) 0.0325(9) Uani 1 1 d . . . . .
H21 H 0.1064 -0.1508 0.4211 0.039 Uiso 1 1 calc R U . . .
C18 C 0.0114(2) -0.1207(6) 0.6583(4) 0.0318(9) Uani 1 1 d . . . . .
H18 H -0.0131 -0.1137 0.7175 0.038 Uiso 1 1 calc R U . . .
O2 O -0.02405(15) 0.4371(5) 0.7540(2) 0.0316(7) Uani 1 1 d . . . . .
C4 C 0.1359(2) 0.3442(6) 0.6532(4) 0.0316(9) Uani 1 1 d . . . . .
H4 H 0.1808 0.3316 0.6771 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2119(2) -0.1673(7) 0.6855(4) 0.0356(10) Uani 1 1 d . . . . .
H15 H 0.2584 -0.1723 0.6946 0.043 Uiso 1 1 calc R U . . .
C7 C -0.0684(2) 0.3953(7) 0.5433(3) 0.0334(9) Uani 1 1 d . . . . .
H7A H -0.0719 0.4336 0.4703 0.050 Uiso 1 1 calc R U . . .
H7B H -0.0897 0.4894 0.5846 0.050 Uiso 1 1 calc R U . . .
H7C H -0.0900 0.2736 0.5501 0.050 Uiso 1 1 calc R U . . .
C10 C -0.1634(2) 0.2383(6) 0.8911(4) 0.0328(9) Uani 1 1 d . . . . .
H10 H -0.1468 0.3613 0.8820 0.039 Uiso 1 1 calc R U . . .
C9 C -0.14983(19) 0.0953(6) 0.8230(3) 0.0304(9) Uani 1 1 d . . . . .
C11 C -0.2014(2) 0.1993(7) 0.9726(4) 0.0351(9) Uani 1 1 d . . . . .
H11 H -0.2109 0.2963 1.0195 0.042 Uiso 1 1 calc R U . . .
C8 C -0.17497(19) -0.0868(6) 0.8329(3) 0.0282(8) Uani 1 1 d . . . . .
C13 C -0.2132(2) -0.1212(6) 0.9157(4) 0.0320(9) Uani 1 1 d . . . . .
C14 C -0.1607(2) -0.2398(7) 0.7583(4) 0.0400(11) Uani 1 1 d . . . . .
H14A H -0.1203 -0.3047 0.7833 0.060 Uiso 1 1 calc R U . . .
H14B H -0.1554 -0.1852 0.6899 0.060 Uiso 1 1 calc R U . . .
H14C H -0.1971 -0.3295 0.7529 0.060 Uiso 1 1 calc R U . . .
C20 C 0.0158(3) -0.1242(6) 0.4719(4) 0.0374(10) Uani 1 1 d . . . . .
H20 H -0.0068 -0.1202 0.4049 0.045 Uiso 1 1 calc R U . . .
C19 C -0.0198(2) -0.1108(6) 0.5605(4) 0.0372(10) Uani 1 1 d . . . . .
H19 H -0.0660 -0.0947 0.5525 0.045 Uiso 1 1 calc R U . . .
C16 C 0.1756(2) -0.1635(7) 0.7743(4) 0.0368(10) Uani 1 1 d . . . . .
H16 H 0.1986 -0.1694 0.8410 0.044 Uiso 1 1 calc R U . . .
C12 C -0.2256(2) 0.0204(6) 0.9862(4) 0.0351(9) Uani 1 1 d . . . . .
H12 H -0.2506 -0.0060 1.0432 0.042 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 C2 1.381(5) . ?
O1 H1O 0.94(9) . ?
N1 C15 1.315(6) . ?
N1 C22 1.371(5) . ?
N2 C16 1.315(6) . ?
N2 C17 1.369(5) . ?
C1 C6 1.395(5) . ?
C1 C2 1.399(5) . ?
C1 C7 1.506(6) . ?
C2 C3 1.396(6) . ?
C22 C17 1.414(5) . ?
C22 C21 1.416(6) . ?
C6 O2 1.383(5) . ?
C6 C5 1.403(6) . ?
C17 C18 1.419(6) . ?
C5 C4 1.399(6) . ?
C5 H5 0.9500 . ?
O3 C9 1.368(5) . ?
O3 H3O 0.8400 . ?
O4 C13 1.366(5) . ?
O4 H4O 0.87(7) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C21 C20 1.373(7) . ?
C21 H21 0.9500 . ?
C18 C19 1.372(7) . ?
C18 H18 0.9500 . ?
O2 H2O 0.83(6) . ?
C4 H4 0.9500 . ?
C15 C16 1.418(6) . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 C11 1.387(6) . ?
C10 C9 1.389(6) . ?
C10 H10 0.9500 . ?
C9 C8 1.405(5) . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C8 C13 1.398(6) . ?
C8 C14 1.500(6) . ?
C13 C12 1.395(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 C19 1.410(7) . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1O 113(5) . . ?
C15 N1 C22 117.0(3) . . ?
C16 N2 C17 116.5(4) . . ?
C6 C1 C2 117.1(3) . . ?
C6 C1 C7 121.5(4) . . ?
C2 C1 C7 121.4(4) . . ?
O1 C2 C3 121.3(3) . . ?
O1 C2 C1 116.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
N1 C22 C17 120.7(4) . . ?
N1 C22 C21 119.6(4) . . ?
C17 C22 C21 119.8(4) . . ?
O2 C6 C1 117.3(3) . . ?
O2 C6 C5 120.4(4) . . ?
C1 C6 C5 122.4(4) . . ?
N2 C17 C22 121.2(4) . . ?
N2 C17 C18 119.3(4) . . ?
C22 C17 C18 119.5(4) . . ?
C4 C5 C6 118.6(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C9 O3 H3O 109.5 . . ?
C13 O4 H4O 112(4) . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C20 C21 C22 119.5(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C6 O2 H2O 110(4) . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C15 C16 122.1(4) . . ?
N1 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O3 C9 C10 121.5(4) . . ?
O3 C9 C8 116.8(4) . . ?
C10 C9 C8 121.7(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C8 C9 117.6(4) . . ?
C13 C8 C14 121.0(4) . . ?
C9 C8 C14 121.4(4) . . ?
O4 C13 C12 122.0(4) . . ?
O4 C13 C8 116.9(4) . . ?
C12 C13 C8 121.1(4) . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
N2 C16 C15 122.5(4) . . ?
N2 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.4(3) . . . . ?
C7 C1 C2 O1 1.2(5) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C7 C1 C2 C3 -179.2(4) . . . . ?
C15 N1 C22 C17 -0.3(6) . . . . ?
C15 N1 C22 C21 178.8(4) . . . . ?
C2 C1 C6 O2 -179.5(3) . . . . ?
C7 C1 C6 O2 -0.1(5) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C7 C1 C6 C5 179.7(4) . . . . ?
C16 N2 C17 C22 2.7(6) . . . . ?
C16 N2 C17 C18 -177.3(4) . . . . ?
N1 C22 C17 N2 -2.2(5) . . . . ?
C21 C22 C17 N2 178.7(4) . . . . ?
N1 C22 C17 C18 177.8(4) . . . . ?
C21 C22 C17 C18 -1.4(6) . . . . ?
O2 C6 C5 C4 179.0(4) . . . . ?
C1 C6 C5 C4 -0.8(6) . . . . ?
O1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
N1 C22 C21 C20 -178.2(4) . . . . ?
C17 C22 C21 C20 0.9(6) . . . . ?
N2 C17 C18 C19 -179.7(4) . . . . ?
C22 C17 C18 C19 0.4(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C6 C5 C4 C3 0.7(6) . . . . ?
C22 N1 C15 C16 2.2(7) . . . . ?
C11 C10 C9 O3 -179.8(4) . . . . ?
C11 C10 C9 C8 1.6(6) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
O3 C9 C8 C13 179.9(4) . . . . ?
C10 C9 C8 C13 -1.5(6) . . . . ?
O3 C9 C8 C14 0.6(6) . . . . ?
C10 C9 C8 C14 179.3(4) . . . . ?
C9 C8 C13 O4 -179.4(4) . . . . ?
C14 C8 C13 O4 -0.1(6) . . . . ?
C9 C8 C13 C12 -0.3(6) . . . . ?
C14 C8 C13 C12 179.0(4) . . . . ?
C22 C21 C20 C19 0.6(6) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C21 C20 C19 C18 -1.6(7) . . . . ?
C17 N2 C16 C15 -0.9(7) . . . . ?
N1 C15 C16 N2 -1.7(8) . . . . ?
C10 C11 C12 C13 -1.7(7) . . . . ?
O4 C13 C12 C11 -179.1(4) . . . . ?
C8 C13 C12 C11 1.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.83(6) 2.00(6) 2.814(5) 166(5) 2_565
O4 H4O N1 0.87(7) 1.95(7) 2.812(5) 172(6) 4_445
O3 H3O O2 0.84 2.06 2.857(5) 158.6 .

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060880'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33

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                   7.821(3)
_cell_length_b                   22.849(8)
_cell_length_c                   8.387(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.286(15)
_cell_angle_gamma                90
_cell_volume                     1498.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13123
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.782
_diffrn_reflns_theta_max         27.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3319
_reflns_number_gt                2922
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0785P)²+0.4464P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
H1O H 0.823(3) 0.1156(11) 0.759(3) 0.061(7) Uiso 1 1 d . . . . .
H2O H 0.514(4) 0.2980(11) 0.296(3) 0.059(7) Uiso 1 1 d . . . . .
O1 O 0.85490(14) 0.14561(5) 0.69457(13) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.61381(16) 0.28294(5) 0.32799(14) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.78807(16) 0.05818(5) 0.91426(14) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.70851(18) 0.16811(6) 0.61968(16) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.73234(18) 0.21339(6) 0.50819(16) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.4203(2) 0.21758(7) 0.46584(19) 0.0331(3) Uani 1 1 d . . . . .
H5 H 0.3229 0.2345 0.4143 0.040 Uiso 1 1 calc R U . . .
N2 N 0.69543(18) -0.03083(6) 1.13057(15) 0.0338(3) Uani 1 1 d . . . . .
C6 C 0.58541(19) 0.23808(6) 0.43409(16) 0.0277(3) Uani 1 1 d . . . . .
C13 C 0.76024(19) -0.04461(6) 0.98314(18) 0.0297(3) Uani 1 1 d . . . . .
C14 C 0.6805(2) 0.02498(7) 1.16699(18) 0.0320(3) Uani 1 1 d . . . . .
C7 C 0.9098(2) 0.23486(7) 0.46748(19) 0.0339(3) Uani 1 1 d . . . . .
H7A H 0.9420 0.2674 0.5380 0.051 Uiso 1 1 calc R U . . .
H7B H 0.9098 0.2481 0.3564 0.051 Uiso 1 1 calc R U . . .
H7C H 0.9922 0.2029 0.4818 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4018(2) 0.17168(7) 0.57500(19) 0.0340(4) Uani 1 1 d . . . . .
H4 H 0.2908 0.1573 0.5966 0.041 Uiso 1 1 calc R U . . .
C15 C 0.72641(19) 0.07094(6) 1.05625(17) 0.0299(3) Uani 1 1 d . . . . .
C8 C 0.80793(18) 0.00003(6) 0.87442(16) 0.0276(3) Uani 1 1 d . . . . .
C12 C 0.7802(2) -0.10425(7) 0.9396(2) 0.0400(4) Uani 1 1 d . . . . .
H12 H 0.7487 -0.1343 1.0114 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5444(2) 0.14673(7) 0.65265(17) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.5304 0.1157 0.7267 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8752(2) -0.01584(8) 0.72403(19) 0.0368(4) Uani 1 1 d . . . . .
H9 H 0.9079 0.0136 0.6509 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7036(3) 0.13446(7) 1.0994(2) 0.0424(4) Uani 1 1 d . . . . .
H16A H 0.7311 0.1590 1.0076 0.064 Uiso 1 1 calc R U . . .
H16B H 0.7802 0.1443 1.1895 0.064 Uiso 1 1 calc R U . . .
H16C H 0.5848 0.1413 1.1290 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8928(2) -0.07422(8) 0.6848(2) 0.0453(4) Uani 1 1 d . . . . .
H10 H 0.9372 -0.0847 0.5842 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6138(3) 0.04048(10) 1.3296(2) 0.0488(5) Uani 1 1 d . . . . .
H17A H 0.5914 0.0045 1.3893 0.073 Uiso 1 1 calc R U . . .
H17B H 0.5076 0.0629 1.3169 0.073 Uiso 1 1 calc R U . . .
H17C H 0.6992 0.0640 1.3879 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8453(2) -0.11857(8) 0.7934(2) 0.0458(4) Uani 1 1 d . . . . .
H11 H 0.8584 -0.1585 0.7651 0.055 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 C2 1.3920(18) . ?
O1 H1O 0.91(3) . ?
O2 C6 1.3786(18) . ?
O2 H2O 0.89(3) . ?
N1 C15 1.3272(19) . ?
N1 C8 1.380(2) . ?
C2 C3 1.407(2) . ?
C2 C1 1.4096(19) . ?
C1 C6 1.412(2) . ?
C1 C7 1.518(2) . ?
C5 C4 1.402(2) . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
N2 C14 1.317(2) . ?
N2 C13 1.383(2) . ?
C13 C12 1.420(2) . ?
C13 C8 1.423(2) . ?
C14 C15 1.453(2) . ?
C14 C17 1.513(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C3 1.400(2) . ?
C4 H4 0.9500 . ?
C15 C16 1.507(2) . ?
C8 C9 1.425(2) . ?
C12 C11 1.377(3) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C10 C11 1.418(3) . ?
C10 H10 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1O 108.3(16) . . ?
C6 O2 H2O 109.2(16) . . ?
C15 N1 C8 118.30(12) . . ?
O1 C2 C3 121.87(13) . . ?
O1 C2 C1 116.80(12) . . ?
C3 C2 C1 121.34(14) . . ?
C2 C1 C6 117.83(13) . . ?
C2 C1 C7 121.43(13) . . ?
C6 C1 C7 120.74(12) . . ?
C4 C5 C6 118.82(14) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C14 N2 C13 117.64(13) . . ?
O2 C6 C5 122.17(14) . . ?
O2 C6 C1 116.10(13) . . ?
C5 C6 C1 121.73(13) . . ?
N2 C13 C12 119.53(14) . . ?
N2 C13 C8 121.08(13) . . ?
C12 C13 C8 119.39(14) . . ?
N2 C14 C15 121.82(13) . . ?
N2 C14 C17 118.03(15) . . ?
C15 C14 C17 120.15(15) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C5 121.05(14) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C15 C14 121.00(13) . . ?
N1 C15 C16 118.30(13) . . ?
C14 C15 C16 120.70(13) . . ?
N1 C8 C13 120.15(13) . . ?
N1 C8 C9 120.36(13) . . ?
C13 C8 C9 119.48(14) . . ?
C11 C12 C13 120.12(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C4 C3 C2 119.20(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C10 C9 C8 119.83(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C10 C11 120.53(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C11 C10 120.65(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 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 C2 C1 C6 -178.21(11) . . . . ?
C3 C2 C1 C6 2.06(19) . . . . ?
O1 C2 C1 C7 2.24(19) . . . . ?
C3 C2 C1 C7 -177.50(13) . . . . ?
C4 C5 C6 O2 179.83(13) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C2 C1 C6 O2 178.87(12) . . . . ?
C7 C1 C6 O2 -1.58(19) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
C7 C1 C6 C5 177.81(13) . . . . ?
C14 N2 C13 C12 179.34(15) . . . . ?
C14 N2 C13 C8 -0.4(2) . . . . ?
C13 N2 C14 C15 1.3(2) . . . . ?
C13 N2 C14 C17 -178.52(15) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C8 N1 C15 C14 -0.2(2) . . . . ?
C8 N1 C15 C16 -179.62(14) . . . . ?
N2 C14 C15 N1 -1.1(2) . . . . ?
C17 C14 C15 N1 178.75(15) . . . . ?
N2 C14 C15 C16 178.39(16) . . . . ?
C17 C14 C15 C16 -1.8(2) . . . . ?
C15 N1 C8 C13 1.0(2) . . . . ?
C15 N1 C8 C9 -179.36(14) . . . . ?
N2 C13 C8 N1 -0.8(2) . . . . ?
C12 C13 C8 N1 179.48(14) . . . . ?
N2 C13 C8 C9 179.60(15) . . . . ?
C12 C13 C8 C9 -0.1(2) . . . . ?
N2 C13 C12 C11 -179.73(15) . . . . ?
C8 C13 C12 C11 0.0(3) . . . . ?
C5 C4 C3 C2 -0.2(2) . . . . ?
O1 C2 C3 C4 179.17(12) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
N1 C8 C9 C10 -179.32(15) . . . . ?
C13 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C13 C12 C11 C10 0.0(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.89(3) 1.97(3) 2.8137(18) 158(2) 4_565
C12 H12 O2 0.95 2.55 3.325(2) 139.5 2_646

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060881'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_weight         260.33

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P bc21'
_space_group_name_Hall           ?

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

_cell_length_a                   9.0198(15)
_cell_length_b                   10.7769(18)
_cell_length_c                   14.653(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1424.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14166
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.257
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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             3257
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.998
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0496P)²+0.3101P]
 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_abs_structure_details 
;
 Flack x determined using 865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.004
_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
N1 N 0.8655(3) 0.8178(3) 0.1587(2) 0.0293(8) Uani 1 1 d . . . . .
O2 O 1.4590(3) 0.9877(3) -0.1546(2) 0.0434(9) Uani 1 1 d . . . . .
H2 H 1.5123 0.9414 -0.1869 0.065 Uiso 1 1 calc R U . . .
O1 O 1.0476(3) 0.9696(3) 0.0436(2) 0.0433(9) Uani 1 1 d . . . . .
H1 H 1.0002 0.9193 0.0762 0.065 Uiso 1 1 calc R U . . .
N2 N 0.6590(3) 0.6610(3) 0.2377(3) 0.0298(8) Uani 1 1 d . . . . .
C5 C 1.3766(4) 0.7887(4) -0.1004(3) 0.0344(10) Uani 1 1 d . . . . .
H5 H 1.4550 0.7481 -0.1317 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6725(5) 0.9399(4) 0.0841(4) 0.0470(12) Uani 1 1 d . . . . .
H12A H 0.6171 0.9069 0.0319 0.070 Uiso 1 1 calc R U . . .
H12B H 0.7604 0.9843 0.0622 0.070 Uiso 1 1 calc R U . . .
H12C H 0.6093 0.9970 0.1186 0.070 Uiso 1 1 calc R U . . .
C6 C 1.3632(4) 0.9166(4) -0.1039(3) 0.0290(9) Uani 1 1 d . . . . .
C10 C 0.8048(4) 0.6440(4) 0.2515(3) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.6162(4) 0.7555(4) 0.1844(3) 0.0276(9) Uani 1 1 d . . . . .
C1 C 1.2528(5) 0.9786(3) -0.0563(4) 0.0296(7) Uani 1 1 d . . . . .
C2 C 1.1536(4) 0.9072(4) -0.0048(3) 0.0288(9) Uani 1 1 d . . . . .
C11 C 0.9079(4) 0.7241(4) 0.2117(3) 0.0258(9) Uani 1 1 d . . . . .
C15 C 1.0718(4) 0.7075(4) 0.2281(3) 0.0385(11) Uani 1 1 d . . . . .
H15A H 1.1265 0.7743 0.1977 0.058 Uiso 1 1 calc R U . . .
H15B H 1.1036 0.6272 0.2035 0.058 Uiso 1 1 calc R U . . .
H15C H 1.0918 0.7101 0.2938 0.058 Uiso 1 1 calc R U . . .
C7 C 1.2396(6) 1.1175(3) -0.0585(5) 0.0537(12) Uani 1 1 d . . . . .
H7A H 1.2616 1.1476 -0.1202 0.081 Uiso 1 1 calc R U . . .
H7B H 1.3101 1.1539 -0.0152 0.081 Uiso 1 1 calc R U . . .
H7C H 1.1385 1.1417 -0.0416 0.081 Uiso 1 1 calc R U . . .
C13 C 0.4527(4) 0.7739(4) 0.1697(3) 0.0396(11) Uani 1 1 d . . . . .
H13A H 0.4220 0.8528 0.1970 0.059 Uiso 1 1 calc R U . . .
H13B H 0.3980 0.7057 0.1985 0.059 Uiso 1 1 calc R U . . .
H13C H 0.4315 0.7750 0.1041 0.059 Uiso 1 1 calc R U . . .
C3 C 1.1615(5) 0.7786(4) -0.0047(3) 0.0343(10) Uani 1 1 d . . . . .
H3 H 1.0894 0.7308 0.0269 0.041 Uiso 1 1 calc R U . . .
C4 C 1.2749(5) 0.7213(3) -0.0509(3) 0.0357(10) Uani 1 1 d . . . . .
H4 H 1.2833 0.6335 -0.0487 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7198(4) 0.8345(3) 0.1450(3) 0.0277(9) Uani 1 1 d . . . . .
C14 C 0.8508(5) 0.5377(4) 0.3104(4) 0.0505(14) Uani 1 1 d . . . . .
H14A H 0.7692 0.4779 0.3148 0.076 Uiso 1 1 calc R U . . .
H14B H 0.8757 0.5683 0.3715 0.076 Uiso 1 1 calc R U . . .
H14C H 0.9377 0.4971 0.2836 0.076 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
N1 C11 1.330(5) . ?
N1 C8 1.341(4) . ?
O2 C6 1.373(5) . ?
O2 H2 0.8400 . ?
O1 C2 1.367(5) . ?
O1 H1 0.8400 . ?
N2 C9 1.341(5) . ?
N2 C10 1.343(5) . ?
C5 C4 1.377(6) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C12 C8 1.506(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C6 C1 1.387(6) . ?
C10 C11 1.396(5) . ?
C10 C14 1.494(6) . ?
C9 C8 1.390(5) . ?
C9 C13 1.503(5) . ?
C1 C2 1.401(6) . ?
C1 C7 1.501(5) . ?
C2 C3 1.389(6) . ?
C11 C15 1.509(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 C4 1.373(6) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C8 118.0(3) . . ?
C6 O2 H2 109.5 . . ?
C2 O1 H1 109.5 . . ?
C9 N2 C10 118.2(3) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C6 C5 121.4(4) . . ?
O2 C6 C1 117.0(3) . . ?
C5 C6 C1 121.6(4) . . ?
N2 C10 C11 120.4(4) . . ?
N2 C10 C14 117.6(4) . . ?
C11 C10 C14 122.0(3) . . ?
N2 C9 C8 120.9(3) . . ?
N2 C9 C13 117.8(3) . . ?
C8 C9 C13 121.3(4) . . ?
C6 C1 C2 117.7(3) . . ?
C6 C1 C7 121.8(4) . . ?
C2 C1 C7 120.6(4) . . ?
O1 C2 C3 121.8(4) . . ?
O1 C2 C1 117.1(3) . . ?
C3 C2 C1 121.1(4) . . ?
N1 C11 C10 121.5(3) . . ?
N1 C11 C15 117.7(3) . . ?
C10 C11 C15 120.9(4) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C8 C9 121.0(4) . . ?
N1 C8 C12 117.9(3) . . ?
C9 C8 C12 121.2(4) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 2.03 2.866(4) 171.9 .
C12 H12B O1 0.98 2.61 3.450(6) 143.8 .
O1 H1 N1 0.84 2.03 2.866(4) 171.9 .
C12 H12B O1 0.98 2.61 3.450(6) 143.8 .

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060882'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35

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'
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                   17.8576(19)
_cell_length_b                   9.9354(10)
_cell_length_c                   18.732(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.457(4)
_cell_angle_gamma                90
_cell_volume                     3203.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33416
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.400
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7382
_reflns_number_gt                5021
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1115P)²+0.9027P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7382
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2461
_refine_ls_wR_factor_gt          0.2029
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
C7 C 0.03200(19) 0.0221(3) -0.09419(17) 0.0447(8) Uani 1 1 d . . . . .
H7A H 0.0513 -0.0656 -0.0732 0.067 Uiso 1 1 calc R U . . .
H7B H 0.0026 0.0107 -0.1460 0.067 Uiso 1 1 calc R U . . .
H7C H -0.0019 0.0606 -0.0660 0.067 Uiso 1 1 calc R U . . .
H14 H 0.4393(19) 0.224(4) 0.3974(18) 0.051(10) Uiso 1 1 d . . . . .
H25 H 0.9502(18) 0.184(3) 1.3804(17) 0.039(9) Uiso 1 1 d . . . . .
H13 H 0.336(2) 0.037(3) 0.4492(18) 0.050(9) Uiso 1 1 d . . . . .
H26 H 0.875(2) 0.412(4) 1.414(2) 0.064(11) Uiso 1 1 d . . . . .
O1 O 0.14174(12) 0.0814(2) 0.03889(11) 0.0417(5) Uani 1 1 d . . . . .
H1O H 0.1788 0.0997 0.0758 0.063 Uiso 1 1 calc R U . . .
O2 O 0.05531(13) 0.1528(2) -0.21852(11) 0.0444(5) Uani 1 1 d . . . . .
H2O H 0.0661 0.1971 -0.2527 0.067 Uiso 1 1 calc R U . . .
O4 O 0.70803(14) 0.4236(2) 1.02670(11) 0.0469(6) Uani 1 1 d . . . . .
H4O H 0.7237 0.3515 1.0491 0.070 Uiso 1 1 calc R U . . .
N3 N 0.77652(15) 0.2791(3) 1.15048(14) 0.0445(6) Uani 1 1 d . . . . .
N2 N 0.53215(15) 0.1127(3) 0.67585(13) 0.0383(6) Uani 1 1 d . . . . .
N1 N 0.24808(14) 0.1343(3) 0.17321(13) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.09932(16) 0.1147(3) -0.09003(15) 0.0307(6) Uani 1 1 d . . . . .
C15 C 0.34261(16) 0.1475(3) 0.31943(15) 0.0348(6) Uani 1 1 d . . . . .
O3 O 0.62726(14) 0.1280(2) 0.81908(11) 0.0465(6) Uani 1 1 d . . . . .
H3O H 0.6022 0.1304 0.7743 0.070 Uiso 1 1 calc R U . . .
C14 C 0.39438(18) 0.1573(3) 0.39506(16) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.50510(17) 0.1812(3) 0.54866(15) 0.0342(6) Uani 1 1 d . . . . .
H9 H 0.5207 0.2315 0.5120 0.041 Uiso 1 1 calc R U . . .
C27 C 0.96300(17) 0.3252(3) 1.50553(16) 0.0381(7) Uani 1 1 d . . . . .
C11 C 0.41854(17) 0.0328(3) 0.58679(15) 0.0416(7) Uani 1 1 d . . . . .
H11 H 0.3730 -0.0211 0.5768 0.050 Uiso 1 1 calc R U . . .
C5 C 0.17569(16) 0.2547(3) -0.15157(15) 0.0343(6) Uani 1 1 d . . . . .
H5 H 0.1828 0.2937 -0.1956 0.041 Uiso 1 1 calc R U . . .
C13 C 0.38395(17) 0.0979(3) 0.45438(15) 0.0357(7) Uani 1 1 d . . . . .
C10 C 0.43642(16) 0.1056(3) 0.52996(14) 0.0318(6) Uani 1 1 d . . . . .
C2 C 0.15453(16) 0.1396(3) -0.02305(15) 0.0320(6) Uani 1 1 d . . . . .
C37 C 0.66785(16) 0.3954(3) 0.95486(15) 0.0331(6) Uani 1 1 d . . . . .
C36 C 0.62348(17) 0.5010(3) 0.91653(17) 0.0380(7) Uani 1 1 d . . . . .
H36 H 0.6228 0.5857 0.9398 0.046 Uiso 1 1 calc R U . . .
C4 C 0.22937(16) 0.2758(3) -0.08456(16) 0.0373(7) Uani 1 1 d . . . . .
H4 H 0.2739 0.3295 -0.0826 0.045 Uiso 1 1 calc R U . . .
N4 N 1.04595(16) 0.2944(3) 1.65495(14) 0.0487(7) Uani 1 1 d . . . . .
C8 C 0.54974(17) 0.1814(3) 0.62129(16) 0.0371(7) Uani 1 1 d . . . . .
H8 H 0.5959 0.2338 0.6331 0.044 Uiso 1 1 calc R U . . .
C25 C 0.91903(18) 0.2590(4) 1.37336(16) 0.0410(7) Uani 1 1 d . . . . .
C32 C 0.67090(16) 0.2700(3) 0.92291(14) 0.0319(6) Uani 1 1 d . . . . .
C33 C 0.62578(16) 0.2517(3) 0.84994(15) 0.0325(6) Uani 1 1 d . . . . .
C35 C 0.58058(17) 0.4811(3) 0.84434(17) 0.0399(7) Uani 1 1 d . . . . .
H35 H 0.5505 0.5526 0.8176 0.048 Uiso 1 1 calc R U . . .
C26 C 0.91637(18) 0.3408(3) 1.42854(16) 0.0400(7) Uani 1 1 d . . . . .
C21 C 0.82475(18) 0.3819(3) 1.26992(16) 0.0417(7) Uani 1 1 d . . . . .
H21 H 0.8248 0.4575 1.3010 0.050 Uiso 1 1 calc R U . . .
C16 C 0.36090(19) 0.2176(4) 0.26265(17) 0.0454(8) Uani 1 1 d . . . . .
H16 H 0.4065 0.2715 0.2722 0.054 Uiso 1 1 calc R U . . .
C3 C 0.21933(16) 0.2199(3) -0.02015(15) 0.0370(7) Uani 1 1 d . . . . .
H3 H 0.2564 0.2360 0.0259 0.044 Uiso 1 1 calc R U . . .
C6 C 0.11071(16) 0.1751(3) -0.15369(14) 0.0319(6) Uani 1 1 d . . . . .
C19 C 0.27550(18) 0.0698(4) 0.30071(16) 0.0444(8) Uani 1 1 d . . . . .
H19 H 0.2600 0.0202 0.3377 0.053 Uiso 1 1 calc R U . . .
C34 C 0.58122(16) 0.3566(3) 0.81060(16) 0.0360(6) Uani 1 1 d . . . . .
H34 H 0.5514 0.3429 0.7609 0.043 Uiso 1 1 calc R U . . .
C38 C 0.72125(19) 0.1586(3) 0.96457(17) 0.0432(7) Uani 1 1 d . . . . .
H38A H 0.7747 0.1912 0.9833 0.065 Uiso 1 1 calc R U . . .
H38B H 0.7203 0.0822 0.9313 0.065 Uiso 1 1 calc R U . . .
H38C H 0.7015 0.1301 1.0062 0.065 Uiso 1 1 calc R U . . .
C28 C 0.9456(2) 0.4003(3) 1.56134(17) 0.0452(8) Uani 1 1 d . . . . .
H28 H 0.9046 0.4642 1.5496 0.054 Uiso 1 1 calc R U . . .
C20 C 0.78004(19) 0.3815(3) 1.19788(16) 0.0422(7) Uani 1 1 d . . . . .
H20 H 0.7495 0.4590 1.1804 0.051 Uiso 1 1 calc R U . . .
C24 C 0.8197(2) 0.1717(4) 1.17651(18) 0.0484(8) Uani 1 1 d . . . . .
H24 H 0.8180 0.0974 1.1442 0.058 Uiso 1 1 calc R U . . .
C31 C 1.02461(18) 0.2348(4) 1.52715(18) 0.0497(9) Uani 1 1 d . . . . .
H31 H 1.0397 0.1817 1.4912 0.060 Uiso 1 1 calc R U . . .
C22 C 0.87020(17) 0.2687(3) 1.29662(16) 0.0381(7) Uani 1 1 d . . . . .
C23 C 0.86690(19) 0.1622(3) 1.24811(17) 0.0450(8) Uani 1 1 d . . . . .
H23 H 0.8968 0.0834 1.2639 0.054 Uiso 1 1 calc R U . . .
C17 C 0.3121(2) 0.2086(4) 0.19175(17) 0.0488(8) Uani 1 1 d . . . . .
H17 H 0.3254 0.2590 0.1538 0.059 Uiso 1 1 calc R U . . .
C18 C 0.23122(18) 0.0651(4) 0.22751(16) 0.0446(8) Uani 1 1 d . . . . .
H18 H 0.1864 0.0093 0.2157 0.054 Uiso 1 1 calc R U . . .
C12 C 0.46702(18) 0.0390(3) 0.65758(16) 0.0414(7) Uani 1 1 d . . . . .
H12 H 0.4535 -0.0115 0.6954 0.050 Uiso 1 1 calc R U . . .
C29 C 0.9878(2) 0.3824(4) 1.63403(18) 0.0503(8) Uani 1 1 d . . . . .
H29 H 0.9748 0.4356 1.6711 0.060 Uiso 1 1 calc R U . . .
C30 C 1.06361(19) 0.2230(4) 1.60145(18) 0.0557(9) Uani 1 1 d . . . . .
H30 H 1.1053 0.1605 1.6150 0.067 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
C7 C1 1.499(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 C2 1.369(3) . ?
O1 H1O 0.8400 . ?
O2 C6 1.365(3) . ?
O2 H2O 0.8400 . ?
O4 C37 1.375(3) . ?
O4 H4O 0.8400 . ?
N3 C24 1.331(4) . ?
N3 C20 1.341(4) . ?
N2 C8 1.334(4) . ?
N2 C12 1.339(4) . ?
N1 C18 1.327(4) . ?
N1 C17 1.327(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.397(4) . ?
C15 C16 1.382(4) . ?
C15 C19 1.390(4) . ?
C15 C14 1.474(4) . ?
O3 C33 1.361(3) . ?
O3 H3O 0.8400 . ?
C14 C13 1.315(4) . ?
C14 H14 1.03(3) . ?
C9 C8 1.381(4) . ?
C9 C10 1.400(4) . ?
C9 H9 0.9500 . ?
C27 C28 1.386(4) . ?
C27 C31 1.394(4) . ?
C27 C26 1.469(4) . ?
C11 C12 1.378(4) . ?
C11 C10 1.393(4) . ?
C11 H11 0.9500 . ?
C5 C4 1.377(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C13 C10 1.477(4) . ?
C13 H13 1.04(3) . ?
C2 C3 1.394(4) . ?
C37 C32 1.390(4) . ?
C37 C36 1.393(4) . ?
C36 C35 1.379(4) . ?
C36 H36 0.9500 . ?
C4 C3 1.383(4) . ?
C4 H4 0.9500 . ?
N4 C30 1.333(5) . ?
N4 C29 1.334(4) . ?
C8 H8 0.9500 . ?
C25 C26 1.325(5) . ?
C25 C22 1.472(4) . ?
C25 H25 0.92(3) . ?
C32 C33 1.401(4) . ?
C32 C38 1.506(4) . ?
C33 C34 1.396(4) . ?
C35 C34 1.390(4) . ?
C35 H35 0.9500 . ?
C26 H26 1.01(4) . ?
C21 C20 1.373(4) . ?
C21 C22 1.399(4) . ?
C21 H21 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C3 H3 0.9500 . ?
C19 C18 1.389(4) . ?
C19 H19 0.9500 . ?
C34 H34 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C28 C29 1.381(4) . ?
C28 H28 0.9500 . ?
C20 H20 0.9500 . ?
C24 C23 1.384(4) . ?
C24 H24 0.9500 . ?
C31 C30 1.385(4) . ?
C31 H31 0.9500 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 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
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 O1 H1O 109.5 . . ?
C6 O2 H2O 109.5 . . ?
C37 O4 H4O 109.5 . . ?
C24 N3 C20 116.5(3) . . ?
C8 N2 C12 116.7(2) . . ?
C18 N1 C17 116.3(3) . . ?
C2 C1 C6 117.6(2) . . ?
C2 C1 C7 121.3(3) . . ?
C6 C1 C7 121.1(2) . . ?
C16 C15 C19 116.8(3) . . ?
C16 C15 C14 119.4(3) . . ?
C19 C15 C14 123.8(3) . . ?
C33 O3 H3O 109.5 . . ?
C13 C14 C15 126.1(3) . . ?
C13 C14 H14 122.4(19) . . ?
C15 C14 H14 111.4(19) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C28 C27 C31 116.5(3) . . ?
C28 C27 C26 120.1(3) . . ?
C31 C27 C26 123.4(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C14 C13 C10 126.2(3) . . ?
C14 C13 H13 119.0(19) . . ?
C10 C13 H13 114.8(19) . . ?
C11 C10 C9 116.8(2) . . ?
C11 C10 C13 119.3(3) . . ?
C9 C10 C13 123.9(3) . . ?
O1 C2 C3 122.2(2) . . ?
O1 C2 C1 116.7(2) . . ?
C3 C2 C1 121.1(3) . . ?
O4 C37 C32 122.3(2) . . ?
O4 C37 C36 115.4(3) . . ?
C32 C37 C36 122.4(3) . . ?
C35 C36 C37 119.2(3) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C30 N4 C29 116.7(3) . . ?
N2 C8 C9 124.2(3) . . ?
N2 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C26 C25 C22 125.9(3) . . ?
C26 C25 H25 122(2) . . ?
C22 C25 H25 112(2) . . ?
C37 C32 C33 117.3(2) . . ?
C37 C32 C38 121.5(2) . . ?
C33 C32 C38 121.2(3) . . ?
O3 C33 C34 121.5(2) . . ?
O3 C33 C32 117.4(2) . . ?
C34 C33 C32 121.1(3) . . ?
C36 C35 C34 120.2(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C25 C26 C27 124.9(3) . . ?
C25 C26 H26 114(2) . . ?
C27 C26 H26 121(2) . . ?
C20 C21 C22 118.6(3) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O2 C6 C5 121.1(2) . . ?
O2 C6 C1 117.0(2) . . ?
C5 C6 C1 121.9(2) . . ?
C18 C19 C15 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?
C35 C34 C33 119.8(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C32 C38 H38A 109.5 . . ?
C32 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C32 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C29 C28 C27 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
N3 C20 C21 124.5(3) . . ?
N3 C20 H20 117.8 . . ?
C21 C20 H20 117.8 . . ?
N3 C24 C23 123.6(3) . . ?
N3 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
C30 C31 C27 119.6(3) . . ?
C30 C31 H31 120.2 . . ?
C27 C31 H31 120.2 . . ?
C23 C22 C21 117.4(3) . . ?
C23 C22 C25 120.1(3) . . ?
C21 C22 C25 122.5(3) . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
N1 C17 C16 124.4(3) . . ?
N1 C17 H17 117.8 . . ?
C16 C17 H17 117.8 . . ?
N1 C18 C19 123.6(3) . . ?
N1 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
N2 C12 C11 123.4(3) . . ?
N2 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N4 C29 C28 123.5(3) . . ?
N4 C29 H29 118.3 . . ?
C28 C29 H29 118.3 . . ?
N4 C30 C31 123.6(3) . . ?
N4 C30 H30 118.2 . . ?
C31 C30 H30 118.2 . . ?

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 C15 C14 C13 179.1(3) . . . . ?
C19 C15 C14 C13 -1.5(5) . . . . ?
C15 C14 C13 C10 178.9(3) . . . . ?
C12 C11 C10 C9 0.9(4) . . . . ?
C12 C11 C10 C13 180.0(3) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C8 C9 C10 C13 179.9(3) . . . . ?
C14 C13 C10 C11 -177.8(3) . . . . ?
C14 C13 C10 C9 1.1(5) . . . . ?
C6 C1 C2 O1 179.0(2) . . . . ?
C7 C1 C2 O1 -3.5(4) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C7 C1 C2 C3 176.4(3) . . . . ?
O4 C37 C36 C35 -179.3(3) . . . . ?
C32 C37 C36 C35 0.3(5) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C12 N2 C8 C9 0.4(4) . . . . ?
C10 C9 C8 N2 0.5(4) . . . . ?
O4 C37 C32 C33 178.2(3) . . . . ?
C36 C37 C32 C33 -1.3(4) . . . . ?
O4 C37 C32 C38 -2.4(4) . . . . ?
C36 C37 C32 C38 178.0(3) . . . . ?
C37 C32 C33 O3 -178.5(3) . . . . ?
C38 C32 C33 O3 2.1(4) . . . . ?
C37 C32 C33 C34 1.6(4) . . . . ?
C38 C32 C33 C34 -177.8(3) . . . . ?
C37 C36 C35 C34 0.5(5) . . . . ?
C22 C25 C26 C27 176.8(3) . . . . ?
C28 C27 C26 C25 -167.8(3) . . . . ?
C31 C27 C26 C25 10.7(5) . . . . ?
C19 C15 C16 C17 0.8(5) . . . . ?
C14 C15 C16 C17 -179.8(3) . . . . ?
C5 C4 C3 C2 0.8(4) . . . . ?
O1 C2 C3 C4 179.8(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C4 C5 C6 O2 179.1(3) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C2 C1 C6 O2 -178.4(2) . . . . ?
C7 C1 C6 O2 4.1(4) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C7 C1 C6 C5 -175.9(3) . . . . ?
C16 C15 C19 C18 0.6(5) . . . . ?
C14 C15 C19 C18 -178.8(3) . . . . ?
C36 C35 C34 C33 -0.3(5) . . . . ?
O3 C33 C34 C35 179.3(3) . . . . ?
C32 C33 C34 C35 -0.8(4) . . . . ?
C31 C27 C28 C29 -0.8(5) . . . . ?
C26 C27 C28 C29 177.9(3) . . . . ?
C24 N3 C20 C21 0.2(5) . . . . ?
C22 C21 C20 N3 0.1(5) . . . . ?
C20 N3 C24 C23 -0.4(5) . . . . ?
C28 C27 C31 C30 1.1(5) . . . . ?
C26 C27 C31 C30 -177.5(3) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C20 C21 C22 C25 -179.0(3) . . . . ?
C26 C25 C22 C23 -166.4(3) . . . . ?
C26 C25 C22 C21 12.4(5) . . . . ?
N3 C24 C23 C22 0.4(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C25 C22 C23 C24 178.8(3) . . . . ?
C18 N1 C17 C16 0.0(5) . . . . ?
C15 C16 C17 N1 -1.1(6) . . . . ?
C17 N1 C18 C19 1.5(5) . . . . ?
C15 C19 C18 N1 -1.8(5) . . . . ?
C8 N2 C12 C11 -0.6(5) . . . . ?
C10 C11 C12 N2 0.0(5) . . . . ?
C30 N4 C29 C28 1.1(5) . . . . ?
C27 C28 C29 N4 -0.3(5) . . . . ?
C29 N4 C30 C31 -0.8(6) . . . . ?
C27 C31 C30 N4 -0.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.84 1.94 2.769(3) 167.5 .
O2 H2O N4 0.84 1.93 2.723(3) 156.8 1_453
O4 H4O N3 0.84 2.01 2.724(3) 141.8 .
O3 H3O N2 0.84 1.94 2.771(3) 169.7 .
O1 H1O N1 0.84 1.94 2.769(3) 167.5 .
O2 H2O N4 0.84 1.93 2.723(3) 156.8 1_453
O3 H3O N2 0.84 1.94 2.771(3) 169.7 .

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060883'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   8.139(2)
_cell_length_b                   12.331(4)
_cell_length_c                   16.793(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.031(13)
_cell_angle_gamma                90
_cell_volume                     1668.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7668
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.020
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1915
_reflns_number_gt                1452
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1215P)²+0.3679P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1915
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.1964
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
H1O H 0.306(4) 0.265(3) 0.3819(18) 0.076(9) Uiso 1 1 d . . . . .
H11A H 1.011(3) 0.431(2) 0.5686(14) 0.041(6) Uiso 1 1 d . . . . .
H11B H 1.062(3) 0.393(2) 0.4864(16) 0.057(7) Uiso 1 1 d . . . . .
C2 C 0.0000 0.2215(2) 0.2500 0.0324(6) Uani 1 2 d S T P . .
O1 O 0.23128(18) 0.22123(13) 0.35122(9) 0.0443(4) Uani 1 1 d . . . . .
C1 C 0.11888(19) 0.28002(16) 0.30105(10) 0.0328(5) Uani 1 1 d . . . . .
N1 N 0.48324(19) 0.33706(14) 0.43331(11) 0.0410(5) Uani 1 1 d . . . . .
C5 C 0.0000 0.1000(2) 0.2500 0.0432(7) Uani 1 2 d S T P . .
H5A H 0.0916 0.0735 0.2893 0.065 Uiso 0.25 1 calc R U P . .
H5B H 0.0139 0.0735 0.1963 0.065 Uiso 0.25 1 calc R U P . .
H5C H -0.1055 0.0735 0.2644 0.065 Uiso 0.25 1 calc R U P . .
H5D H -0.0916 0.0735 0.2107 0.065 Uiso 0.25 1 calc R U P . .
H5E H -0.0139 0.0735 0.3037 0.065 Uiso 0.25 1 calc R U P . .
H5F H 0.1055 0.0735 0.2356 0.065 Uiso 0.25 1 calc R U P . .
C4 C 0.1205(2) 0.39359(16) 0.30061(11) 0.0367(5) Uani 1 1 d . . . . .
H4 H 0.2035 0.4322 0.3347 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8098(2) 0.40488(15) 0.48504(11) 0.0346(4) Uani 1 1 d . . . . .
C3 C 0.0000 0.4490(2) 0.2500 0.0395(6) Uani 1 2 d S T P . .
H3 H 0.0000 0.5260 0.2500 0.047 Uiso 1 2 calc R U P . .
C9 C 0.6978(2) 0.38824(16) 0.53865(12) 0.0384(5) Uani 1 1 d . . . . .
H9 H 0.7309 0.3995 0.5946 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5376(2) 0.35521(17) 0.51074(12) 0.0408(5) Uani 1 1 d . . . . .
H10 H 0.4627 0.3449 0.5487 0.049 Uiso 1 1 calc R U . . .
C11 C 0.9861(2) 0.44125(16) 0.51175(13) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.7522(3) 0.38780(19) 0.40421(13) 0.0452(5) Uani 1 1 d . . . . .
H7 H 0.8233 0.3995 0.3647 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5914(3) 0.3537(2) 0.38190(13) 0.0477(6) Uani 1 1 d . . . . .
H6 H 0.5553 0.3413 0.3264 0.057 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
C2 C1 1.400(2) 2 ?
C2 C1 1.400(2) . ?
C2 C5 1.498(4) . ?
O1 C1 1.363(2) . ?
O1 H1O 0.92(3) . ?
C1 C4 1.400(3) . ?
N1 C6 1.332(3) . ?
N1 C10 1.333(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5D 0.9800 . ?
C5 H5E 0.9800 . ?
C5 H5F 0.9800 . ?
C4 C3 1.385(2) . ?
C4 H4 0.9500 . ?
C8 C9 1.383(3) . ?
C8 C7 1.389(3) . ?
C8 C11 1.511(2) . ?
C3 C4 1.385(2) 2 ?
C3 H3 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C11 1.527(4) 5_766 ?
C11 H11A 0.96(2) . ?
C11 H11B 0.99(3) . ?
C7 C6 1.376(3) . ?
C7 H7 0.9500 . ?
C6 H6 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
C1 C2 C1 117.9(2) 2 . ?
C1 C2 C5 121.04(12) 2 . ?
C1 C2 C5 121.05(12) . . ?
C1 O1 H1O 112(2) . . ?
O1 C1 C2 116.80(18) . . ?
O1 C1 C4 121.94(16) . . ?
C2 C1 C4 121.25(17) . . ?
C6 N1 C10 116.54(17) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C5 H5D 109.5 . . ?
H5A C5 H5D 141.1 . . ?
H5B C5 H5D 56.3 . . ?
H5C C5 H5D 56.3 . . ?
C2 C5 H5E 109.5 . . ?
H5A C5 H5E 56.3 . . ?
H5B C5 H5E 141.1 . . ?
H5C C5 H5E 56.3 . . ?
H5D C5 H5E 109.5 . . ?
C2 C5 H5F 109.5 . . ?
H5A C5 H5F 56.3 . . ?
H5B C5 H5F 56.3 . . ?
H5C C5 H5F 141.1 . . ?
H5D C5 H5F 109.5 . . ?
H5E C5 H5F 109.5 . . ?
C3 C4 C1 119.32(17) . . ?
C3 C4 H4 120.3 . . ?
C1 C4 H4 120.3 . . ?
C9 C8 C7 116.81(17) . . ?
C9 C8 C11 122.40(17) . . ?
C7 C8 C11 120.78(18) . . ?
C4 C3 C4 120.9(3) . 2 ?
C4 C3 H3 119.5 . . ?
C4 C3 H3 119.5 2 . ?
C8 C9 C10 119.91(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 123.28(18) . . ?
N1 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C8 C11 C11 111.95(19) . 5_766 ?
C8 C11 H11A 108.6(14) . . ?
C11 C11 H11A 111.1(15) 5_766 . ?
C8 C11 H11B 108.4(16) . . ?
C11 C11 H11B 109.4(16) 5_766 . ?
H11A C11 H11B 107(2) . . ?
C6 C7 C8 119.37(19) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
N1 C6 C7 124.1(2) . . ?
N1 C6 H6 118.0 . . ?
C7 C6 H6 118.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C1 O1 178.80(17) 2 . . . ?
C5 C2 C1 O1 -1.20(17) . . . . ?
C1 C2 C1 C4 -0.74(11) 2 . . . ?
C5 C2 C1 C4 179.26(11) . . . . ?
O1 C1 C4 C3 -178.04(14) . . . . ?
C2 C1 C4 C3 1.5(2) . . . . ?
C1 C4 C3 C4 -0.72(11) . . . 2 ?
C7 C8 C9 C10 0.6(3) . . . . ?
C11 C8 C9 C10 179.81(18) . . . . ?
C6 N1 C10 C9 -0.9(3) . . . . ?
C8 C9 C10 N1 0.6(3) . . . . ?
C9 C8 C11 C11 -108.1(3) . . . 5_766 ?
C7 C8 C11 C11 71.1(3) . . . 5_766 ?
C9 C8 C7 C6 -1.3(3) . . . . ?
C11 C8 C7 C6 179.4(2) . . . . ?
C10 N1 C6 C7 0.0(3) . . . . ?
C8 C7 C6 N1 1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O1 0.95 2.59 3.531(3) 169.3 7_556

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060884'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N4 O2'
_chemical_formula_weight         308.34

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/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                   18.468(3)
_cell_length_b                   7.2386(11)
_cell_length_c                   11.831(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.866(10)
_cell_angle_gamma                90
_cell_volume                     1580.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16108
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.103
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3628
_reflns_number_gt                3110
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1053P)²+0.7025P]
 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         3628
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1852
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
N3 N 0.42858(10) 0.4549(3) 0.13245(15) 0.0392(4) Uani 1 1 d . . . . .
N2 N 0.97408(9) 0.9579(2) 1.02070(14) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.52041(9) 0.4725(3) 0.46230(14) 0.0377(4) Uani 1 1 d . . . . .
O1 O 0.85309(8) 0.1305(2) 0.78755(13) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.8735 0.2307 0.8049 0.059 Uiso 1 1 calc R U . . .
N1 N 0.91513(10) 0.4575(2) 0.86078(15) 0.0351(4) Uani 1 1 d . . . . .
O2 O 0.66168(9) -0.1085(2) 0.55958(15) 0.0491(5) Uani 1 1 d . . . . .
H2 H 0.6363 -0.0847 0.5012 0.074 Uiso 1 1 calc R U . . .
C9 C 0.53126(12) 0.4466(3) 0.26091(18) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.5823 0.4367 0.2725 0.046 Uiso 1 1 calc R U . . .
C15 C 0.95613(10) 0.7891(3) 0.96252(16) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.80127(11) 0.3243(3) 0.63933(18) 0.0354(5) Uani 1 1 d . . . . .
H3 H 0.8334 0.4228 0.6583 0.043 Uiso 1 1 calc R U . . .
C13 C 0.97922(12) 0.5361(3) 0.84029(18) 0.0362(5) Uani 1 1 d . . . . .
H13 H 1.0105 0.4756 0.7899 0.043 Uiso 1 1 calc R U . . .
C6 C 0.70642(11) 0.0378(3) 0.58420(17) 0.0346(4) Uani 1 1 d . . . . .
C16 C 0.89023(11) 0.7084(3) 0.98628(19) 0.0371(5) Uani 1 1 d . . . . .
H16 H 0.8584 0.7646 1.0376 0.045 Uiso 1 1 calc R U . . .
C14 C 1.00202(11) 0.7009(3) 0.88892(17) 0.0324(4) Uani 1 1 d . . . . .
H14 H 1.0478 0.7523 0.8724 0.039 Uiso 1 1 calc R U . . .
C5 C 0.70362(11) 0.2007(3) 0.52216(18) 0.0371(5) Uani 1 1 d . . . . .
H5 H 0.6694 0.2149 0.4611 0.044 Uiso 1 1 calc R U . . .
C17 C 0.87200(11) 0.5431(3) 0.93291(19) 0.0379(5) Uani 1 1 d . . . . .
H17 H 0.8267 0.4881 0.9484 0.045 Uiso 1 1 calc R U . . .
C2 C 0.80398(10) 0.1596(3) 0.70091(16) 0.0312(4) Uani 1 1 d . . . . .
C11 C 0.41210(12) 0.4812(3) 0.33216(18) 0.0392(5) Uani 1 1 d . . . . .
H11 H 0.3800 0.4931 0.3929 0.047 Uiso 1 1 calc R U . . .
C10 C 0.48624(11) 0.4682(3) 0.35187(16) 0.0332(4) Uani 1 1 d . . . . .
C1 C 0.75668(11) 0.0133(3) 0.67441(17) 0.0335(4) Uani 1 1 d . . . . .
C12 C 0.38641(12) 0.4762(3) 0.22188(19) 0.0411(5) Uani 1 1 d . . . . .
H12 H 0.3357 0.4886 0.2081 0.049 Uiso 1 1 calc R U . . .
C4 C 0.75139(12) 0.3423(3) 0.55055(19) 0.0392(5) Uani 1 1 d . . . . .
H4 H 0.7498 0.4538 0.5081 0.047 Uiso 1 1 calc R U . . .
C8 C 0.50001(12) 0.4399(3) 0.15310(18) 0.0394(5) Uani 1 1 d . . . . .
H8 H 0.5307 0.4238 0.0909 0.047 Uiso 1 1 calc R U . . .
C7 C 0.76098(16) -0.1642(3) 0.7401(2) 0.0542(7) Uani 1 1 d . . . . .
H7A H 0.8113 -0.1872 0.7649 0.081 Uiso 1 1 calc R U . . .
H7B H 0.7438 -0.2663 0.6919 0.081 Uiso 1 1 calc R U . . .
H7C H 0.7306 -0.1550 0.8063 0.081 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
N3 C8 1.338(3) . ?
N3 C12 1.343(3) . ?
N2 N2 1.248(3) 3_777 ?
N2 C15 1.436(2) . ?
N4 N4 1.251(3) 3_666 ?
N4 C10 1.433(3) . ?
O1 C2 1.363(2) . ?
O1 H1 0.8400 . ?
N1 C17 1.338(3) . ?
N1 C13 1.342(3) . ?
O2 C6 1.369(2) . ?
O2 H2 0.8400 . ?
C9 C8 1.384(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C15 C16 1.387(3) . ?
C15 C14 1.390(3) . ?
C3 C4 1.381(3) . ?
C3 C2 1.397(3) . ?
C3 H3 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C6 C5 1.389(3) . ?
C6 C1 1.403(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C14 H14 0.9500 . ?
C5 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C2 C1 1.402(3) . ?
C11 C12 1.374(3) . ?
C11 C10 1.385(3) . ?
C11 H11 0.9500 . ?
C1 C7 1.502(3) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N3 C12 117.32(18) . . ?
N2 N2 C15 113.3(2) 3_777 . ?
N4 N4 C10 113.5(2) 3_666 . ?
C2 O1 H1 109.5 . . ?
C17 N1 C13 117.74(17) . . ?
C6 O2 H2 109.5 . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C16 C15 C14 119.35(18) . . ?
C16 C15 N2 116.86(17) . . ?
C14 C15 N2 123.73(17) . . ?
C4 C3 C2 119.27(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N1 C13 C14 123.26(19) . . ?
N1 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
O2 C6 C5 122.18(18) . . ?
O2 C6 C1 116.37(18) . . ?
C5 C6 C1 121.44(18) . . ?
C15 C16 C17 118.17(19) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C13 C14 C15 118.22(18) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C6 C5 C4 119.15(19) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C17 C16 123.24(19) . . ?
N1 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
O1 C2 C3 122.39(17) . . ?
O1 C2 C1 116.49(17) . . ?
C3 C2 C1 121.11(18) . . ?
C12 C11 C10 117.85(19) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C10 C9 119.37(19) . . ?
C11 C10 N4 123.77(18) . . ?
C9 C10 N4 116.85(18) . . ?
C6 C1 C2 117.83(18) . . ?
C6 C1 C7 121.60(18) . . ?
C2 C1 C7 120.57(19) . . ?
N3 C12 C11 124.0(2) . . ?
N3 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C3 C4 C5 121.21(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N3 C8 C9 123.0(2) . . ?
N3 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N2 C15 C16 -166.2(2) 3_777 . . . ?
N2 N2 C15 C14 16.6(3) 3_777 . . . ?
C17 N1 C13 C14 -0.7(3) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
N2 C15 C16 C17 -178.79(18) . . . . ?
N1 C13 C14 C15 -0.1(3) . . . . ?
C16 C15 C14 C13 1.2(3) . . . . ?
N2 C15 C14 C13 178.32(18) . . . . ?
O2 C6 C5 C4 -178.9(2) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C13 N1 C17 C16 0.4(3) . . . . ?
C15 C16 C17 N1 0.7(3) . . . . ?
C4 C3 C2 O1 178.20(19) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C12 C11 C10 C9 -1.5(3) . . . . ?
C12 C11 C10 N4 179.6(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 N4 179.32(19) . . . . ?
N4 N4 C10 C11 -14.2(3) 3_666 . . . ?
N4 N4 C10 C9 166.9(2) 3_666 . . . ?
O2 C6 C1 C2 179.18(19) . . . . ?
C5 C6 C1 C2 0.5(3) . . . . ?
O2 C6 C1 C7 0.0(3) . . . . ?
C5 C6 C1 C7 -178.6(2) . . . . ?
O1 C2 C1 C6 -178.81(18) . . . . ?
C3 C2 C1 C6 -0.1(3) . . . . ?
O1 C2 C1 C7 0.3(3) . . . . ?
C3 C2 C1 C7 179.0(2) . . . . ?
C8 N3 C12 C11 -0.8(3) . . . . ?
C10 C11 C12 N3 1.7(4) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C12 N3 C8 C9 -0.5(3) . . . . ?
C10 C9 C8 N3 0.7(3) . . . . ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060885'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34

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                   7.656(7)
_cell_length_b                   22.46(2)
_cell_length_c                   8.940(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.516(14)
_cell_angle_gamma                90
_cell_volume                     1537(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15342
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3506
_reflns_number_gt                2734
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1157P)²+0.2680P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.067(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3506
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2240
_refine_ls_wR_factor_gt          0.1997
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
H2O H 0.596(5) 0.3019(14) 1.176(3) 0.069(9) Uiso 1 1 d . . . . .
H1O H 0.290(5) 0.117(2) 0.719(4) 0.109(13) Uiso 1 1 d . . . . .
O1 O 0.2587(2) 0.15269(7) 0.7826(2) 0.0522(5) Uani 1 1 d . . . . .
N1 N 0.2810(2) 0.05368(8) 0.60765(19) 0.0398(4) Uani 1 1 d . . . . .
N2 N 0.2258(2) -0.04169(8) 0.4051(2) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.3796(3) 0.22042(8) 0.9578(2) 0.0372(5) Uani 1 1 d . . . . .
C1 C 0.4065(3) 0.17577(9) 0.8521(2) 0.0394(5) Uani 1 1 d . . . . .
O2 O 0.4972(2) 0.28703(7) 1.1352(2) 0.0538(5) Uani 1 1 d . . . . .
C14 C 0.1851(3) -0.04637(9) 0.5500(2) 0.0372(5) Uani 1 1 d . . . . .
C6 C 0.5723(3) 0.15516(10) 0.8207(3) 0.0473(5) Uani 1 1 d . . . . .
H6 H 0.5873 0.1247 0.7485 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6953(3) 0.22403(9) 1.0008(3) 0.0419(5) Uani 1 1 d . . . . .
H4 H 0.7942 0.2406 1.0518 0.050 Uiso 1 1 calc R U . . .
C3 C 0.5273(3) 0.24419(8) 1.0307(2) 0.0379(5) Uani 1 1 d . . . . .
C13 C 0.2937(3) 0.01006(10) 0.3616(2) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.3210(3) 0.05856(10) 0.4632(2) 0.0408(5) Uani 1 1 d . . . . .
C19 C 0.2129(2) 0.00168(9) 0.6525(2) 0.0361(5) Uani 1 1 d . . . . .
C15 C 0.1110(3) -0.10080(11) 0.6029(3) 0.0536(6) Uani 1 1 d . . . . .
H15 H 0.0895 -0.1330 0.5360 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7158(3) 0.17957(11) 0.8958(3) 0.0475(6) Uani 1 1 d . . . . .
H5 H 0.8296 0.1656 0.8749 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1672(3) -0.00632(12) 0.8049(2) 0.0508(6) Uani 1 1 d . . . . .
H18 H 0.1839 0.0254 0.8743 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1991(3) 0.24052(12) 0.9981(3) 0.0563(7) Uani 1 1 d . . . . .
H7A H 0.1585 0.2712 0.9274 0.084 Uiso 1 1 calc R U . . .
H7B H 0.2023 0.2569 1.0997 0.084 Uiso 1 1 calc R U . . .
H7C H 0.1189 0.2065 0.9935 0.084 Uiso 1 1 calc R U . . .
C12 C 0.3407(3) 0.01765(16) 0.2089(3) 0.0646(8) Uani 1 1 d . . . . .
H12 H 0.3239 -0.0142 0.1401 0.077 Uiso 1 1 calc R U . . .
C9 C 0.3939(3) 0.11289(13) 0.4092(3) 0.0635(8) Uani 1 1 d . . . . .
H9 H 0.4130 0.1456 0.4749 0.076 Uiso 1 1 calc R U . . .
C17 C 0.1006(3) -0.05856(15) 0.8512(3) 0.0647(8) Uani 1 1 d . . . . .
H17 H 0.0727 -0.0635 0.9534 0.078 Uiso 1 1 calc R U . . .
C16 C 0.0717(3) -0.10585(14) 0.7501(4) 0.0655(8) Uani 1 1 d . . . . .
H16 H 0.0238 -0.1421 0.7854 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4357(4) 0.11701(19) 0.2620(5) 0.0845(12) Uani 1 1 d . . . . .
H10 H 0.4845 0.1531 0.2263 0.101 Uiso 1 1 calc R U . . .
C11 C 0.4087(4) 0.0695(2) 0.1620(4) 0.0846(12) Uani 1 1 d . . . . .
H11 H 0.4386 0.0740 0.0602 0.102 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 1.378(3) . ?
O1 H1O 1.01(4) . ?
N1 C8 1.339(3) . ?
N1 C19 1.344(3) . ?
N2 C13 1.335(3) . ?
N2 C14 1.344(3) . ?
C2 C3 1.396(3) . ?
C2 C1 1.396(3) . ?
C2 C7 1.507(3) . ?
C1 C6 1.387(3) . ?
O2 C3 1.364(3) . ?
O2 H2O 0.90(4) . ?
C14 C19 1.428(3) . ?
C14 C15 1.433(3) . ?
C6 C5 1.385(3) . ?
C6 H6 0.9500 . ?
C4 C5 1.382(3) . ?
C4 C3 1.396(3) . ?
C4 H4 0.9500 . ?
C13 C8 1.430(3) . ?
C13 C12 1.431(3) . ?
C8 C9 1.431(3) . ?
C19 C18 1.428(3) . ?
C15 C16 1.363(4) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C18 C17 1.349(4) . ?
C18 H18 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C12 C11 1.347(5) . ?
C12 H12 0.9500 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9500 . ?
C17 C16 1.408(5) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C10 C11 1.404(6) . ?
C10 H10 0.9500 . ?
C11 H11 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
C1 O1 H1O 110(2) . . ?
C8 N1 C19 117.30(18) . . ?
C13 N2 C14 116.80(18) . . ?
C3 C2 C1 117.28(19) . . ?
C3 C2 C7 120.7(2) . . ?
C1 C2 C7 121.96(19) . . ?
O1 C1 C6 121.9(2) . . ?
O1 C1 C2 116.20(19) . . ?
C6 C1 C2 121.9(2) . . ?
C3 O2 H2O 113(2) . . ?
N2 C14 C19 121.65(19) . . ?
N2 C14 C15 119.2(2) . . ?
C19 C14 C15 119.1(2) . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O2 C3 C4 122.24(19) . . ?
O2 C3 C2 116.06(19) . . ?
C4 C3 C2 121.7(2) . . ?
N2 C13 C8 121.9(2) . . ?
N2 C13 C12 119.4(2) . . ?
C8 C13 C12 118.6(2) . . ?
N1 C8 C13 121.12(19) . . ?
N1 C8 C9 119.8(2) . . ?
C13 C8 C9 119.1(2) . . ?
N1 C19 C18 120.0(2) . . ?
N1 C19 C14 121.18(19) . . ?
C18 C19 C14 118.8(2) . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 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
C3 C2 C1 O1 179.50(18) . . . . ?
C7 C2 C1 O1 2.4(3) . . . . ?
C3 C2 C1 C6 0.5(3) . . . . ?
C7 C2 C1 C6 -176.6(2) . . . . ?
C13 N2 C14 C19 0.1(3) . . . . ?
C13 N2 C14 C15 179.68(18) . . . . ?
O1 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C5 C4 C3 O2 178.6(2) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C1 C2 C3 O2 -178.96(18) . . . . ?
C7 C2 C3 O2 -1.8(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C7 C2 C3 C4 176.6(2) . . . . ?
C14 N2 C13 C8 -0.4(3) . . . . ?
C14 N2 C13 C12 179.62(19) . . . . ?
C19 N1 C8 C13 -0.6(3) . . . . ?
C19 N1 C8 C9 -179.99(19) . . . . ?
N2 C13 C8 N1 0.7(3) . . . . ?
C12 C13 C8 N1 -179.32(19) . . . . ?
N2 C13 C8 C9 -179.9(2) . . . . ?
C12 C13 C8 C9 0.1(3) . . . . ?
C8 N1 C19 C18 -179.92(18) . . . . ?
C8 N1 C19 C14 0.2(3) . . . . ?
N2 C14 C19 N1 0.0(3) . . . . ?
C15 C14 C19 N1 -179.57(18) . . . . ?
N2 C14 C19 C18 -179.80(18) . . . . ?
C15 C14 C19 C18 0.6(3) . . . . ?
N2 C14 C15 C16 179.2(2) . . . . ?
C19 C14 C15 C16 -1.2(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C1 C6 C5 C4 -0.2(4) . . . . ?
N1 C19 C18 C17 -179.3(2) . . . . ?
C14 C19 C18 C17 0.6(3) . . . . ?
N2 C13 C12 C11 179.7(2) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
N1 C8 C9 C10 179.3(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C19 C18 C17 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C18 C17 C16 C15 0.5(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C13 C12 C11 C10 0.4(4) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 1.01(4) 1.74(4) 2.726(3) 164(4) .
C15 H15 O2 0.95 2.44 3.386(4) 174.2 2_546

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.139

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060886'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35

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'
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                   7.742(4)
_cell_length_b                   22.159(11)
_cell_length_c                   9.100(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.630(5)
_cell_angle_gamma                90
_cell_volume                     1558.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15898
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3558
_reflns_number_gt                3122
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0800P)²+0.2786P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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
H2O H 0.545(3) 0.3023(10) 0.682(3) 0.063(6) Uiso 1 1 d . . . . .
H1O H 0.243(3) 0.1185(12) 0.227(3) 0.071(7) Uiso 1 1 d . . . . .
O1 O 0.21643(15) 0.15307(5) 0.28053(13) 0.0398(3) Uani 1 1 d . . . . .
N1 N 0.23924(16) 0.55597(5) 0.38756(14) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.44828(15) 0.28852(5) 0.63941(13) 0.0409(3) Uani 1 1 d . . . . .
C2 C 0.33307(18) 0.22134(6) 0.46021(16) 0.0300(3) Uani 1 1 d . . . . .
C1 C 0.36016(19) 0.17721(6) 0.35434(16) 0.0313(3) Uani 1 1 d . . . . .
C3 C 0.47962(19) 0.24587(6) 0.53583(15) 0.0305(3) Uani 1 1 d . . . . .
C6 C 0.5259(2) 0.15805(7) 0.32557(18) 0.0386(4) Uani 1 1 d . . . . .
H6 H 0.5416 0.1281 0.2530 0.046 Uiso 1 1 calc R U . . .
C20 C 0.29467(18) 0.50269(6) 0.33645(15) 0.0295(3) Uani 1 1 d . . . . .
C14 C 0.2730(2) 0.45556(7) 0.57417(17) 0.0361(3) Uani 1 1 d . . . . .
H14 H 0.2867 0.4217 0.6380 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6459(2) 0.22694(7) 0.50933(18) 0.0367(3) Uani 1 1 d . . . . .
H4 H 0.7434 0.2438 0.5630 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2111(2) 0.50958(7) 0.62730(16) 0.0352(3) Uani 1 1 d . . . . .
C8 C 0.19757(19) 0.55992(7) 0.52881(17) 0.0336(3) Uani 1 1 d . . . . .
C5 C 0.6675(2) 0.18304(8) 0.40350(19) 0.0418(4) Uani 1 1 d . . . . .
H5 H 0.7807 0.1700 0.3843 0.050 Uiso 1 1 calc R U . . .
C15 C 0.31527(19) 0.45039(6) 0.42827(16) 0.0312(3) Uani 1 1 d . . . . .
C19 C 0.3342(2) 0.49804(8) 0.18612(17) 0.0411(4) Uani 1 1 d . . . . .
H19 H 0.3201 0.5321 0.1232 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3779(2) 0.39603(7) 0.3664(2) 0.0437(4) Uani 1 1 d . . . . .
H16 H 0.3940 0.3611 0.4264 0.052 Uiso 1 1 calc R U . . .
C17 C 0.4147(2) 0.39374(9) 0.2230(2) 0.0501(5) Uani 1 1 d . . . . .
H17 H 0.4561 0.3573 0.1832 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1543(2) 0.24122(8) 0.4956(2) 0.0446(4) Uani 1 1 d . . . . .
H7A H 0.1262 0.2794 0.4454 0.067 Uiso 1 1 calc R U . . .
H7B H 0.1506 0.2468 0.6022 0.067 Uiso 1 1 calc R U . . .
H7C H 0.0700 0.2104 0.4622 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1383(2) 0.61633(9) 0.5816(2) 0.0498(5) Uani 1 1 d . . . . .
H9 H 0.1306 0.6503 0.5179 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1606(2) 0.51774(10) 0.77480(19) 0.0529(5) Uani 1 1 d . . . . .
H12 H 0.1678 0.4848 0.8417 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3919(2) 0.44510(9) 0.13228(19) 0.0497(5) Uani 1 1 d . . . . .
H18 H 0.4173 0.4426 0.0317 0.060 Uiso 1 1 calc R U . . .
C10 C 0.0929(3) 0.62160(11) 0.7225(3) 0.0633(6) Uani 1 1 d . . . . .
H10 H 0.0536 0.6594 0.7565 0.076 Uiso 1 1 calc R U . . .
C11 C 0.1028(3) 0.57194(12) 0.8197(2) 0.0640(7) Uani 1 1 d . . . . .
H11 H 0.0687 0.5766 0.9175 0.077 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 1.3714(18) . ?
O1 H1O 0.94(3) . ?
N1 C8 1.348(2) . ?
N1 C20 1.3491(19) . ?
O2 C3 1.3672(19) . ?
O2 H2O 0.88(3) . ?
C2 C1 1.398(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.506(2) . ?
C1 C6 1.392(2) . ?
C3 C4 1.389(2) . ?
C6 C5 1.383(2) . ?
C6 H6 0.9500 . ?
C20 C19 1.424(2) . ?
C20 C15 1.432(2) . ?
C14 C13 1.388(2) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C13 C8 1.431(2) . ?
C13 C12 1.433(2) . ?
C8 C9 1.425(2) . ?
C5 H5 0.9500 . ?
C15 C16 1.427(2) . ?
C19 C18 1.358(3) . ?
C19 H19 0.9500 . ?
C16 C17 1.354(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.411(3) . ?
C17 H17 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.356(3) . ?
C9 H9 0.9500 . ?
C12 C11 1.354(3) . ?
C12 H12 0.9500 . ?
C18 H18 0.9500 . ?
C10 C11 1.411(4) . ?
C10 H10 0.9500 . ?
C11 H11 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
C1 O1 H1O 112.0(15) . . ?
C8 N1 C20 119.09(12) . . ?
C3 O2 H2O 111.1(15) . . ?
C1 C2 C3 117.28(13) . . ?
C1 C2 C7 122.13(13) . . ?
C3 C2 C7 120.57(14) . . ?
O1 C1 C6 121.19(14) . . ?
O1 C1 C2 117.25(13) . . ?
C6 C1 C2 121.55(14) . . ?
O2 C3 C4 122.36(13) . . ?
O2 C3 C2 115.71(13) . . ?
C4 C3 C2 121.92(14) . . ?
C5 C6 C1 119.45(15) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C20 C19 119.13(13) . . ?
N1 C20 C15 122.24(13) . . ?
C19 C20 C15 118.64(14) . . ?
C13 C14 C15 120.70(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C5 C4 C3 119.11(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C14 C13 C8 117.88(14) . . ?
C14 C13 C12 123.77(16) . . ?
C8 C13 C12 118.35(16) . . ?
N1 C8 C9 118.70(15) . . ?
N1 C8 C13 122.30(13) . . ?
C9 C8 C13 119.00(15) . . ?
C6 C5 C4 120.69(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C14 C15 C16 123.48(14) . . ?
C14 C15 C20 117.76(13) . . ?
C16 C15 C20 118.76(14) . . ?
C18 C19 C20 120.31(16) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C17 C16 C15 120.59(16) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.52(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C19 C18 C17 121.17(16) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C9 C10 C11 121.23(19) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.58(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 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
C3 C2 C1 O1 179.84(12) . . . . ?
C7 C2 C1 O1 1.3(2) . . . . ?
C3 C2 C1 C6 0.4(2) . . . . ?
C7 C2 C1 C6 -178.19(15) . . . . ?
C1 C2 C3 O2 -179.46(12) . . . . ?
C7 C2 C3 O2 -0.9(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C7 C2 C3 C4 177.69(14) . . . . ?
O1 C1 C6 C5 -179.30(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C8 N1 C20 C19 178.29(13) . . . . ?
C8 N1 C20 C15 -1.7(2) . . . . ?
O2 C3 C4 C5 179.35(14) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C15 C14 C13 C8 -1.9(2) . . . . ?
C15 C14 C13 C12 178.25(15) . . . . ?
C20 N1 C8 C9 -179.69(14) . . . . ?
C20 N1 C8 C13 0.4(2) . . . . ?
C14 C13 C8 N1 1.4(2) . . . . ?
C12 C13 C8 N1 -178.79(14) . . . . ?
C14 C13 C8 C9 -178.50(14) . . . . ?
C12 C13 C8 C9 1.3(2) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C13 C14 C15 C16 -179.37(14) . . . . ?
C13 C14 C15 C20 0.8(2) . . . . ?
N1 C20 C15 C14 1.1(2) . . . . ?
C19 C20 C15 C14 -178.86(14) . . . . ?
N1 C20 C15 C16 -178.75(13) . . . . ?
C19 C20 C15 C16 1.3(2) . . . . ?
N1 C20 C19 C18 179.34(15) . . . . ?
C15 C20 C19 C18 -0.7(2) . . . . ?
C14 C15 C16 C17 179.15(16) . . . . ?
C20 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
N1 C8 C9 C10 179.01(17) . . . . ?
C13 C8 C9 C10 -1.1(3) . . . . ?
C14 C13 C12 C11 179.35(17) . . . . ?
C8 C13 C12 C11 -0.5(2) . . . . ?
C20 C19 C18 C17 -0.2(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C13 C12 C11 C10 -0.7(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.94(3) 1.75(3) 2.6746(19) 171(2) 2_545

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060887'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H26 N2 O2'
_chemical_formula_weight         482.56

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.097(17)
_cell_length_b                   12.117(19)
_cell_length_c                   12.53(2)
_cell_angle_alpha                73.19(5)
_cell_angle_beta                 81.98(5)
_cell_angle_gamma                75.42(5)
_cell_volume                     1276(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13607
_diffrn_reflns_av_unetI/netI     0.1527
_diffrn_reflns_av_R_equivalents  0.1668
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         27.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5860
_reflns_number_gt                2004
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1592P)²]
 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         5860
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2668
_refine_ls_R_factor_gt           0.1231
_refine_ls_wR_factor_ref         0.3809
_refine_ls_wR_factor_gt          0.2833
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.1634(4) 0.6312(3) 0.1670(3) 0.0725(11) Uani 1 1 d . . . . .
H1 H 0.1177 0.6418 0.1098 0.109 Uiso 1 1 calc R U . . .
O2 O 0.3406(4) 0.8401(3) 0.3664(3) 0.0768(12) Uani 1 1 d . . . . .
H2 H 0.3814 0.8979 0.3551 0.115 Uiso 1 1 calc R U . . .
C3 C 0.2856(5) 0.8419(4) 0.2696(4) 0.0488(11) Uani 1 1 d . . . . .
N1 N 0.4175(5) 1.0488(4) 0.3636(3) 0.0653(12) Uani 1 1 d . . . . .
C2 C 0.2524(4) 0.7361(4) 0.2666(3) 0.0416(10) Uani 1 1 d . . . . .
C1 C 0.1945(5) 0.7354(4) 0.1687(4) 0.0522(12) Uani 1 1 d . . . . .
C20 C 0.3252(7) 1.1261(5) 0.4169(4) 0.0656(15) Uani 1 1 d . . . . .
C14 C 0.5216(8) 1.2291(5) 0.4094(4) 0.0761(18) Uani 1 1 d . . . . .
H14 H 0.5569 1.2899 0.4249 0.091 Uiso 1 1 calc R U . . .
C8 C 0.5604(7) 1.0612(5) 0.3310(4) 0.0665(14) Uani 1 1 d . . . . .
C13 C 0.6190(7) 1.1531(5) 0.3533(4) 0.0677(16) Uani 1 1 d . . . . .
C4 C 0.2636(6) 0.9417(4) 0.1802(4) 0.0631(14) Uani 1 1 d . . . . .
H4 H 0.2888 1.0122 0.1833 0.076 Uiso 1 1 calc R U . . .
C15 C 0.3744(7) 1.2175(4) 0.4432(4) 0.0695(16) Uani 1 1 d . . . . .
C7 C 0.2806(6) 0.6271(4) 0.3633(4) 0.0661(14) Uani 1 1 d . . . . .
H7A H 0.2342 0.5672 0.3517 0.099 Uiso 1 1 calc R U . . .
H7B H 0.2354 0.6475 0.4328 0.099 Uiso 1 1 calc R U . . .
H7C H 0.3905 0.5958 0.3685 0.099 Uiso 1 1 calc R U . . .
C19 C 0.1723(7) 1.1141(5) 0.4500(5) 0.0753(16) Uani 1 1 d . . . . .
H19 H 0.1365 1.0545 0.4327 0.090 Uiso 1 1 calc R U . . .
C12 C 0.7737(8) 1.1593(6) 0.3146(5) 0.0861(19) Uani 1 1 d . . . . .
H12 H 0.8147 1.2182 0.3285 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2040(6) 0.9368(4) 0.0860(4) 0.0743(16) Uani 1 1 d . . . . .
H5 H 0.1870 1.0051 0.0245 0.089 Uiso 1 1 calc R U . . .
C6 C 0.1691(6) 0.8350(4) 0.0801(4) 0.0747(17) Uani 1 1 d . . . . .
H6 H 0.1277 0.8332 0.0152 0.090 Uiso 1 1 calc R U . . .
C9 C 0.6588(8) 0.9835(5) 0.2719(5) 0.0815(17) Uani 1 1 d . . . . .
H9 H 0.6217 0.9234 0.2568 0.098 Uiso 1 1 calc R U . . .
C11 C 0.8624(8) 1.0833(7) 0.2589(6) 0.098(2) Uani 1 1 d . . . . .
H11 H 0.9643 1.0895 0.2343 0.117 Uiso 1 1 calc R U . . .
C16 C 0.2714(8) 1.2941(5) 0.5019(5) 0.0876(19) Uani 1 1 d . . . . .
H16 H 0.3035 1.3557 0.5186 0.105 Uiso 1 1 calc R U . . .
C10 C 0.8040(9) 0.9931(6) 0.2367(5) 0.093(2) Uani 1 1 d . . . . .
H10 H 0.8671 0.9402 0.1973 0.112 Uiso 1 1 calc R U . . .
C18 C 0.0765(8) 1.1889(6) 0.5071(5) 0.0914(19) Uani 1 1 d . . . . .
H18 H -0.0253 1.1806 0.5290 0.110 Uiso 1 1 calc R U . . .
C17 C 0.1285(9) 1.2784(6) 0.5334(6) 0.097(2) Uani 1 1 d . . . . .
H17 H 0.0613 1.3282 0.5741 0.117 Uiso 1 1 calc R U . . .
C26 C 0.1198(6) 0.6012(4) 0.8921(4) 0.0623(14) Uani 1 1 d . . . . .
C27 C -0.1051(7) 0.6235(5) 0.7978(5) 0.0743(17) Uani 1 1 d . . . . .
H27 H -0.1528 0.6129 0.7398 0.089 Uiso 1 1 calc R U . . .
N2 N 0.0348(6) 0.6510(3) 0.9703(3) 0.0649(12) Uani 1 1 d . . . . .
C33 C -0.1942(7) 0.6755(4) 0.8758(4) 0.0659(15) Uani 1 1 d . . . . .
C21 C 0.0526(7) 0.5858(4) 0.8004(4) 0.0691(16) Uani 1 1 d . . . . .
C28 C -0.1194(7) 0.6887(4) 0.9639(4) 0.0643(15) Uani 1 1 d . . . . .
C25 C 0.2816(7) 0.5637(4) 0.8964(5) 0.0747(16) Uani 1 1 d . . . . .
H25 H 0.3282 0.5741 0.9550 0.090 Uiso 1 1 calc R U . . .
C22 C 0.1533(9) 0.5308(5) 0.7218(5) 0.0877(19) Uani 1 1 d . . . . .
H22 H 0.1120 0.5192 0.6613 0.105 Uiso 1 1 calc R U . . .
C29 C -0.2086(8) 0.7417(5) 1.0460(5) 0.0817(17) Uani 1 1 d . . . . .
H29 H -0.1609 0.7503 1.1050 0.098 Uiso 1 1 calc R U . . .
C24 C 0.3700(8) 0.5138(5) 0.8188(6) 0.0915(19) Uani 1 1 d . . . . .
H24 H 0.4773 0.4909 0.8230 0.110 Uiso 1 1 calc R U . . .
C23 C 0.3034(9) 0.4957(6) 0.7316(6) 0.097(2) Uani 1 1 d . . . . .
H23 H 0.3662 0.4579 0.6793 0.116 Uiso 1 1 calc R U . . .
C32 C -0.3547(8) 0.7161(6) 0.8750(6) 0.092(2) Uani 1 1 d . . . . .
H32 H -0.4055 0.7078 0.8174 0.110 Uiso 1 1 calc R U . . .
C31 C -0.4372(8) 0.7663(6) 0.9543(7) 0.103(2) Uani 1 1 d . . . . .
H31 H -0.5447 0.7920 0.9524 0.124 Uiso 1 1 calc R U . . .
C30 C -0.3633(8) 0.7805(6) 1.0405(6) 0.095(2) Uani 1 1 d . . . . .
H30 H -0.4216 0.8172 1.0950 0.114 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 1.368(5) . ?
O1 H1 0.8400 . ?
O2 C3 1.369(5) . ?
O2 H2 0.8400 . ?
C3 C4 1.383(6) . ?
C3 C2 1.401(6) . ?
N1 C8 1.340(7) . ?
N1 C20 1.355(7) . ?
C2 C1 1.404(6) . ?
C2 C7 1.506(6) . ?
C1 C6 1.377(7) . ?
C20 C19 1.426(8) . ?
C20 C15 1.428(7) . ?
C14 C15 1.376(8) . ?
C14 C13 1.385(8) . ?
C14 H14 0.9500 . ?
C8 C9 1.424(8) . ?
C8 C13 1.456(7) . ?
C13 C12 1.437(8) . ?
C4 C5 1.388(6) . ?
C4 H4 0.9500 . ?
C15 C16 1.430(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C19 C18 1.377(8) . ?
C19 H19 0.9500 . ?
C12 C11 1.352(8) . ?
C12 H12 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.355(8) . ?
C9 H9 0.9500 . ?
C11 C10 1.436(9) . ?
C11 H11 0.9500 . ?
C16 C17 1.350(9) . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?
C18 C17 1.420(8) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C26 N2 1.348(7) . ?
C26 C25 1.431(8) . ?
C26 C21 1.451(7) . ?
C27 C33 1.374(8) . ?
C27 C21 1.393(8) . ?
C27 H27 0.9500 . ?
N2 C28 1.368(7) . ?
C33 C32 1.419(8) . ?
C33 C28 1.440(7) . ?
C21 C22 1.440(8) . ?
C28 C29 1.420(8) . ?
C25 C24 1.354(8) . ?
C25 H25 0.9500 . ?
C22 C23 1.335(8) . ?
C22 H22 0.9500 . ?
C29 C30 1.372(8) . ?
C29 H29 0.9500 . ?
C24 C23 1.414(9) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
C32 C31 1.354(9) . ?
C32 H32 0.9500 . ?
C31 C30 1.420(9) . ?
C31 H31 0.9500 . ?
C30 H30 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
C1 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
O2 C3 C4 122.3(4) . . ?
O2 C3 C2 115.7(4) . . ?
C4 C3 C2 122.0(4) . . ?
C8 N1 C20 118.4(5) . . ?
C3 C2 C1 117.1(4) . . ?
C3 C2 C7 121.4(4) . . ?
C1 C2 C7 121.5(4) . . ?
O1 C1 C6 122.2(4) . . ?
O1 C1 C2 116.3(4) . . ?
C6 C1 C2 121.5(4) . . ?
N1 C20 C19 118.4(5) . . ?
N1 C20 C15 123.1(6) . . ?
C19 C20 C15 118.5(6) . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C8 C9 119.7(5) . . ?
N1 C8 C13 121.9(6) . . ?
C9 C8 C13 118.4(6) . . ?
C14 C13 C12 124.4(6) . . ?
C14 C13 C8 117.9(6) . . ?
C12 C13 C8 117.7(6) . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C14 C15 C20 117.8(6) . . ?
C14 C15 C16 122.2(5) . . ?
C20 C15 C16 120.0(6) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C18 C19 C20 120.0(6) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C11 C12 C13 121.5(6) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C6 C5 C4 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C10 C9 C8 121.8(6) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C12 C11 C10 120.6(7) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C17 C16 C15 119.6(6) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C9 C10 C11 120.0(7) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C19 C18 C17 120.6(7) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C17 C18 121.3(7) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
N2 C26 C25 120.2(5) . . ?
N2 C26 C21 122.0(5) . . ?
C25 C26 C21 117.8(6) . . ?
C33 C27 C21 122.5(5) . . ?
C33 C27 H27 118.7 . . ?
C21 C27 H27 118.7 . . ?
C26 N2 C28 119.6(4) . . ?
C27 C33 C32 124.0(6) . . ?
C27 C33 C28 117.6(5) . . ?
C32 C33 C28 118.3(6) . . ?
C27 C21 C22 125.7(5) . . ?
C27 C21 C26 116.7(6) . . ?
C22 C21 C26 117.6(6) . . ?
N2 C28 C29 119.5(5) . . ?
N2 C28 C33 121.6(6) . . ?
C29 C28 C33 118.9(6) . . ?
C24 C25 C26 121.6(6) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C23 C22 C21 121.7(6) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C30 C29 C28 120.3(6) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C25 C24 C23 120.4(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C22 C23 C24 120.9(7) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C31 C32 C33 121.6(7) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C32 C31 C30 120.0(7) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 C31 120.8(7) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?

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
O2 C3 C2 C1 179.5(4) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?
O2 C3 C2 C7 -1.7(6) . . . . ?
C4 C3 C2 C7 178.4(4) . . . . ?
C3 C2 C1 O1 179.7(4) . . . . ?
C7 C2 C1 O1 0.9(6) . . . . ?
C3 C2 C1 C6 -1.0(7) . . . . ?
C7 C2 C1 C6 -179.8(5) . . . . ?
C8 N1 C20 C19 179.0(4) . . . . ?
C8 N1 C20 C15 -2.2(7) . . . . ?
C20 N1 C8 C9 -178.2(4) . . . . ?
C20 N1 C8 C13 1.3(7) . . . . ?
C15 C14 C13 C12 179.6(5) . . . . ?
C15 C14 C13 C8 0.2(7) . . . . ?
N1 C8 C13 C14 -0.4(7) . . . . ?
C9 C8 C13 C14 179.2(4) . . . . ?
N1 C8 C13 C12 -179.9(4) . . . . ?
C9 C8 C13 C12 -0.3(6) . . . . ?
O2 C3 C4 C5 -178.5(5) . . . . ?
C2 C3 C4 C5 1.3(8) . . . . ?
C13 C14 C15 C20 -1.0(7) . . . . ?
C13 C14 C15 C16 179.6(5) . . . . ?
N1 C20 C15 C14 2.0(7) . . . . ?
C19 C20 C15 C14 -179.1(4) . . . . ?
N1 C20 C15 C16 -178.6(4) . . . . ?
C19 C20 C15 C16 0.3(7) . . . . ?
N1 C20 C19 C18 178.2(5) . . . . ?
C15 C20 C19 C18 -0.7(7) . . . . ?
C14 C13 C12 C11 -179.1(5) . . . . ?
C8 C13 C12 C11 0.3(8) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C4 C5 C6 C1 -0.4(9) . . . . ?
O1 C1 C6 C5 -179.3(5) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
N1 C8 C9 C10 179.6(5) . . . . ?
C13 C8 C9 C10 0.1(8) . . . . ?
C13 C12 C11 C10 -0.1(9) . . . . ?
C14 C15 C16 C17 -179.7(5) . . . . ?
C20 C15 C16 C17 0.9(8) . . . . ?
C8 C9 C10 C11 0.2(9) . . . . ?
C12 C11 C10 C9 -0.2(9) . . . . ?
C20 C19 C18 C17 0.0(8) . . . . ?
C15 C16 C17 C18 -1.6(9) . . . . ?
C19 C18 C17 C16 1.2(9) . . . . ?
C25 C26 N2 C28 178.6(4) . . . . ?
C21 C26 N2 C28 -0.2(7) . . . . ?
C21 C27 C33 C32 179.3(5) . . . . ?
C21 C27 C33 C28 -1.1(7) . . . . ?
C33 C27 C21 C22 -180.0(5) . . . . ?
C33 C27 C21 C26 1.5(7) . . . . ?
N2 C26 C21 C27 -0.9(7) . . . . ?
C25 C26 C21 C27 -179.7(4) . . . . ?
N2 C26 C21 C22 -179.5(4) . . . . ?
C25 C26 C21 C22 1.6(7) . . . . ?
C26 N2 C28 C29 -179.7(4) . . . . ?
C26 N2 C28 C33 0.6(7) . . . . ?
C27 C33 C28 N2 0.0(7) . . . . ?
C32 C33 C28 N2 179.6(4) . . . . ?
C27 C33 C28 C29 -179.7(4) . . . . ?
C32 C33 C28 C29 -0.1(7) . . . . ?
N2 C26 C25 C24 -179.8(5) . . . . ?
C21 C26 C25 C24 -0.9(7) . . . . ?
C27 C21 C22 C23 -179.0(5) . . . . ?
C26 C21 C22 C23 -0.4(8) . . . . ?
N2 C28 C29 C30 179.7(5) . . . . ?
C33 C28 C29 C30 -0.6(7) . . . . ?
C26 C25 C24 C23 -1.0(9) . . . . ?
C21 C22 C23 C24 -1.5(10) . . . . ?
C25 C24 C23 C22 2.3(10) . . . . ?
C27 C33 C32 C31 179.7(6) . . . . ?
C28 C33 C32 C31 0.1(8) . . . . ?
C33 C32 C31 C30 0.6(10) . . . . ?
C28 C29 C30 C31 1.3(9) . . . . ?
C32 C31 C30 C29 -1.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.96 2.796(6) 172.1 1_554
O2 H2 N1 0.84 1.97 2.778(6) 160.4 .

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.123

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060888'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H34 N4 O4'
_chemical_formula_weight         550.64

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.734(5)
_cell_length_b                   9.196(6)
_cell_length_c                   20.844(14)
_cell_angle_alpha                101.370(15)
_cell_angle_beta                 94.21(3)
_cell_angle_gamma                96.022(17)
_cell_volume                     1438.6(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15403
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.001
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6586
_reflns_number_gt                3999
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1041P)²+0.0406P]
 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         6586
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2307
_refine_ls_wR_factor_gt          0.1821
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.1210(2) 0.0590(2) 0.13059(10) 0.0348(5) Uani 1 1 d . . . . .
H1O H 0.1522 -0.0244 0.1148 0.052 Uiso 1 1 calc R U . . .
O3 O 0.3780(2) 0.3090(2) 0.65801(10) 0.0321(5) Uani 1 1 d . . . . .
H3O H 0.3478 0.3576 0.6298 0.048 Uiso 1 1 calc R U . . .
O4 O 0.1444(2) 0.0144(2) 0.79924(10) 0.0342(5) Uani 1 1 d . . . . .
H4O H 0.0513 -0.0087 0.8152 0.051 Uiso 1 1 calc R U . . .
O2 O 0.3567(3) 0.5409(2) 0.24728(11) 0.0377(5) Uani 1 1 d . . . . .
H2O H 0.4478 0.5841 0.2706 0.057 Uiso 1 1 calc R U . . .
N1 N 0.2957(3) 0.4385(3) 0.55303(11) 0.0294(5) Uani 1 1 d . . . . .
C10 C 0.1130(3) 0.1033(3) 0.75505(13) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.2593(3) 0.1589(3) 0.72728(13) 0.0249(6) Uani 1 1 d . . . . .
C2 C 0.2393(3) 0.3012(3) 0.18887(13) 0.0266(6) Uani 1 1 d . . . . .
C1 C 0.2661(3) 0.1592(3) 0.15571(13) 0.0269(6) Uani 1 1 d . . . . .
C8 C 0.2314(3) 0.2510(3) 0.68290(13) 0.0263(6) Uani 1 1 d . . . . .
C3 C 0.3871(4) 0.4028(3) 0.21476(14) 0.0286(6) Uani 1 1 d . . . . .
C13 C 0.0647(4) 0.2847(3) 0.66487(14) 0.0310(6) Uani 1 1 d . . . . .
H13 H 0.0487 0.3476 0.6343 0.037 Uiso 1 1 calc R U . . .
N3 N -0.1903(3) 0.2024(3) 0.93140(15) 0.0456(7) Uani 1 1 d . . . . .
C6 C 0.4336(4) 0.1207(3) 0.14750(14) 0.0315(6) Uani 1 1 d . . . . .
H6 H 0.4497 0.0240 0.1242 0.038 Uiso 1 1 calc R U . . .
N4 N -0.2765(3) 0.6227(3) 1.03521(12) 0.0390(6) Uani 1 1 d . . . . .
C12 C -0.0774(4) 0.2241(3) 0.69265(15) 0.0337(7) Uani 1 1 d . . . . .
H12 H -0.1915 0.2451 0.6805 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5765(4) 0.2245(3) 0.17360(15) 0.0338(7) Uani 1 1 d . . . . .
H5 H 0.6911 0.1983 0.1686 0.041 Uiso 1 1 calc R U . . .
N2 N 0.2063(3) 0.5696(3) 0.44461(12) 0.0329(6) Uani 1 1 d . . . . .
C33 C 0.3052(3) 0.3657(3) 0.49062(14) 0.0281(6) Uani 1 1 d . . . . .
C14 C 0.4382(3) 0.1161(3) 0.74325(15) 0.0314(6) Uani 1 1 d . . . . .
H14A H 0.5067 0.1172 0.7056 0.047 Uiso 1 1 calc R U . . .
H14B H 0.4265 0.0156 0.7529 0.047 Uiso 1 1 calc R U . . .
H14C H 0.4977 0.1877 0.7816 0.047 Uiso 1 1 calc R U . . .
C22 C 0.2411(3) 0.5756(3) 0.56185(14) 0.0280(6) Uani 1 1 d . . . . .
C11 C -0.0547(3) 0.1340(3) 0.73756(14) 0.0305(6) Uani 1 1 d . . . . .
H11 H -0.1522 0.0934 0.7563 0.037 Uiso 1 1 calc R U . . .
C28 C 0.2610(3) 0.4335(3) 0.43615(14) 0.0306(6) Uani 1 1 d . . . . .
C32 C 0.3616(4) 0.2201(3) 0.47825(16) 0.0374(7) Uani 1 1 d . . . . .
H32 H 0.3914 0.1737 0.5137 0.045 Uiso 1 1 calc R U . . .
C27 C 0.1960(3) 0.6412(3) 0.50672(14) 0.0293(6) Uani 1 1 d . . . . .
C16 C -0.2539(4) 0.3615(4) 1.03064(16) 0.0403(7) Uani 1 1 d . . . . .
H16 H -0.2788 0.3698 1.0751 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0572(3) 0.3435(4) 0.19722(15) 0.0353(7) Uani 1 1 d . . . . .
H7A H -0.0164 0.3081 0.1556 0.053 Uiso 1 1 calc R U . . .
H7B H 0.0628 0.4524 0.2101 0.053 Uiso 1 1 calc R U . . .
H7C H 0.0073 0.2973 0.2313 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5547(3) 0.3659(3) 0.20687(14) 0.0319(7) Uani 1 1 d . . . . .
H4 H 0.6533 0.4372 0.2242 0.038 Uiso 1 1 calc R U . . .
C18 C -0.2171(4) 0.4609(4) 0.93479(15) 0.0389(7) Uani 1 1 d . . . . .
H18 H -0.2152 0.5402 0.9117 0.047 Uiso 1 1 calc R U . . .
C29 C 0.2746(4) 0.3530(4) 0.37093(14) 0.0374(7) Uani 1 1 d . . . . .
H29 H 0.2456 0.3963 0.3344 0.045 Uiso 1 1 calc R U . . .
C17 C -0.2494(3) 0.4868(3) 1.00164(14) 0.0316(7) Uani 1 1 d . . . . .
C23 C 0.2267(4) 0.6551(3) 0.62683(15) 0.0350(7) Uani 1 1 d . . . . .
H23 H 0.2573 0.6127 0.6635 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2221(5) 0.2273(4) 0.99479(18) 0.0474(8) Uani 1 1 d . . . . .
H15 H -0.2227 0.1455 1.0164 0.057 Uiso 1 1 calc R U . . .
C26 C 0.1382(4) 0.7860(4) 0.51950(17) 0.0407(8) Uani 1 1 d . . . . .
H26 H 0.1086 0.8322 0.4839 0.049 Uiso 1 1 calc R U . . .
C19 C -0.1887(4) 0.3217(4) 0.90341(17) 0.0484(9) Uani 1 1 d . . . . .
H19 H -0.1661 0.3086 0.8586 0.058 Uiso 1 1 calc R U . . .
C25 C 0.1252(4) 0.8581(4) 0.58217(19) 0.0470(9) Uani 1 1 d . . . . .
H25 H 0.0864 0.9541 0.5899 0.056 Uiso 1 1 calc R U . . .
C20 C -0.3048(5) 0.6444(4) 1.10479(16) 0.0488(9) Uani 1 1 d . . . . .
H20A H -0.4046 0.5746 1.1105 0.073 Uiso 1 1 calc R U . . .
H20B H -0.3287 0.7472 1.1207 0.073 Uiso 1 1 calc R U . . .
H20C H -0.2001 0.6259 1.1299 0.073 Uiso 1 1 calc R U . . .
C21 C -0.2705(5) 0.7524(4) 1.0044(2) 0.0558(10) Uani 1 1 d . . . . .
H21A H -0.1573 0.7675 0.9869 0.084 Uiso 1 1 calc R U . . .
H21B H -0.2859 0.8412 1.0372 0.084 Uiso 1 1 calc R U . . .
H21C H -0.3642 0.7354 0.9685 0.084 Uiso 1 1 calc R U . . .
C30 C 0.3287(4) 0.2150(4) 0.36103(16) 0.0445(8) Uani 1 1 d . . . . .
H30 H 0.3374 0.1625 0.3175 0.053 Uiso 1 1 calc R U . . .
C31 C 0.3722(4) 0.1489(4) 0.41508(17) 0.0444(8) Uani 1 1 d . . . . .
H31 H 0.4097 0.0524 0.4071 0.053 Uiso 1 1 calc R U . . .
C24 C 0.1690(4) 0.7918(4) 0.63628(17) 0.0418(8) Uani 1 1 d . . . . .
H24 H 0.1579 0.8436 0.6797 0.050 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 1.374(3) . ?
O1 H1O 0.8400 . ?
O3 C8 1.381(3) . ?
O3 H3O 0.8400 . ?
O4 C10 1.371(3) . ?
O4 H4O 0.8400 . ?
O2 C3 1.369(3) . ?
O2 H2O 0.8400 . ?
N1 C33 1.352(4) . ?
N1 C22 1.354(4) . ?
C10 C11 1.394(4) . ?
C10 C9 1.403(4) . ?
C9 C8 1.392(4) . ?
C9 C14 1.510(4) . ?
C2 C1 1.396(4) . ?
C2 C3 1.399(4) . ?
C2 C7 1.513(4) . ?
C1 C6 1.393(4) . ?
C8 C13 1.399(4) . ?
C3 C4 1.387(4) . ?
C13 C12 1.395(4) . ?
C13 H13 0.9500 . ?
N3 C19 1.340(5) . ?
N3 C15 1.341(5) . ?
C6 C5 1.384(4) . ?
C6 H6 0.9500 . ?
N4 C17 1.352(4) . ?
N4 C21 1.459(4) . ?
N4 C20 1.460(4) . ?
C12 C11 1.381(4) . ?
C12 H12 0.9500 . ?
C5 C4 1.382(4) . ?
C5 H5 0.9500 . ?
N2 C27 1.344(4) . ?
N2 C28 1.347(4) . ?
C33 C32 1.432(4) . ?
C33 C28 1.436(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C22 C23 1.425(4) . ?
C22 C27 1.437(4) . ?
C11 H11 0.9500 . ?
C28 C29 1.431(4) . ?
C32 C31 1.362(5) . ?
C32 H32 0.9500 . ?
C27 C26 1.431(4) . ?
C16 C15 1.367(5) . ?
C16 C17 1.401(4) . ?
C16 H16 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 H4 0.9500 . ?
C18 C19 1.365(5) . ?
C18 C17 1.412(4) . ?
C18 H18 0.9500 . ?
C29 C30 1.360(5) . ?
C29 H29 0.9500 . ?
C23 C24 1.361(4) . ?
C23 H23 0.9500 . ?
C15 H15 0.9500 . ?
C26 C25 1.359(5) . ?
C26 H26 0.9500 . ?
C19 H19 0.9500 . ?
C25 C24 1.420(5) . ?
C25 H25 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C30 C31 1.418(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C24 H24 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
C1 O1 H1O 109.5 . . ?
C8 O3 H3O 109.5 . . ?
C10 O4 H4O 109.5 . . ?
C3 O2 H2O 109.5 . . ?
C33 N1 C22 117.6(2) . . ?
O4 C10 C11 122.1(2) . . ?
O4 C10 C9 116.0(2) . . ?
C11 C10 C9 121.8(3) . . ?
C8 C9 C10 117.2(2) . . ?
C8 C9 C14 121.6(2) . . ?
C10 C9 C14 121.2(2) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 C7 121.3(2) . . ?
C3 C2 C7 121.1(3) . . ?
O1 C1 C6 121.0(3) . . ?
O1 C1 C2 117.7(2) . . ?
C6 C1 C2 121.3(3) . . ?
O3 C8 C9 116.3(2) . . ?
O3 C8 C13 121.6(2) . . ?
C9 C8 C13 122.1(3) . . ?
O2 C3 C4 122.1(3) . . ?
O2 C3 C2 116.2(2) . . ?
C4 C3 C2 121.7(3) . . ?
C12 C13 C8 118.6(3) . . ?
C12 C13 H13 120.7 . . ?
C8 C13 H13 120.7 . . ?
C19 N3 C15 115.2(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C17 N4 C21 121.6(3) . . ?
C17 N4 C20 120.1(3) . . ?
C21 N4 C20 118.2(3) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C27 N2 C28 117.1(3) . . ?
N1 C33 C32 120.1(3) . . ?
N1 C33 C28 120.6(3) . . ?
C32 C33 C28 119.3(3) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C22 C23 119.3(3) . . ?
N1 C22 C27 121.0(3) . . ?
C23 C22 C27 119.6(3) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N2 C28 C29 119.2(3) . . ?
N2 C28 C33 122.0(3) . . ?
C29 C28 C33 118.8(3) . . ?
C31 C32 C33 119.4(3) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
N2 C27 C26 120.3(3) . . ?
N2 C27 C22 121.6(3) . . ?
C26 C27 C22 118.1(3) . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
N4 C17 C16 122.2(3) . . ?
N4 C17 C18 122.4(3) . . ?
C16 C17 C18 115.4(3) . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N3 C15 C16 125.0(3) . . ?
N3 C15 H15 117.5 . . ?
C16 C15 H15 117.5 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
N3 C19 C18 124.6(3) . . ?
N3 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 121.7(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C23 C24 C25 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?

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
O4 C10 C9 C8 -179.2(2) . . . . ?
C11 C10 C9 C8 2.2(4) . . . . ?
O4 C10 C9 C14 2.8(4) . . . . ?
C11 C10 C9 C14 -175.8(3) . . . . ?
C3 C2 C1 O1 179.6(2) . . . . ?
C7 C2 C1 O1 0.3(4) . . . . ?
C3 C2 C1 C6 -1.2(4) . . . . ?
C7 C2 C1 C6 179.4(3) . . . . ?
C10 C9 C8 O3 177.7(2) . . . . ?
C14 C9 C8 O3 -4.4(4) . . . . ?
C10 C9 C8 C13 -1.6(4) . . . . ?
C14 C9 C8 C13 176.3(3) . . . . ?
C1 C2 C3 O2 -179.7(2) . . . . ?
C7 C2 C3 O2 -0.3(4) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C7 C2 C3 C4 -179.3(3) . . . . ?
O3 C8 C13 C12 -179.0(2) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
O1 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C8 C13 C12 C11 0.7(4) . . . . ?
C1 C6 C5 C4 -0.8(4) . . . . ?
C22 N1 C33 C32 -179.8(2) . . . . ?
C22 N1 C33 C28 0.9(4) . . . . ?
C33 N1 C22 C23 179.0(2) . . . . ?
C33 N1 C22 C27 -0.4(4) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
O4 C10 C11 C12 -179.9(3) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C27 N2 C28 C29 -179.8(2) . . . . ?
C27 N2 C28 C33 0.6(4) . . . . ?
N1 C33 C28 N2 -1.1(4) . . . . ?
C32 C33 C28 N2 179.6(3) . . . . ?
N1 C33 C28 C29 179.4(2) . . . . ?
C32 C33 C28 C29 0.1(4) . . . . ?
N1 C33 C32 C31 -179.3(3) . . . . ?
C28 C33 C32 C31 0.0(4) . . . . ?
C28 N2 C27 C26 -179.7(3) . . . . ?
C28 N2 C27 C22 -0.1(4) . . . . ?
N1 C22 C27 N2 0.0(4) . . . . ?
C23 C22 C27 N2 -179.4(3) . . . . ?
N1 C22 C27 C26 179.6(3) . . . . ?
C23 C22 C27 C26 0.2(4) . . . . ?
C6 C5 C4 C3 0.9(4) . . . . ?
O2 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
N2 C28 C29 C30 -179.7(3) . . . . ?
C33 C28 C29 C30 -0.1(4) . . . . ?
C21 N4 C17 C16 179.6(3) . . . . ?
C20 N4 C17 C16 2.5(4) . . . . ?
C21 N4 C17 C18 -1.3(4) . . . . ?
C20 N4 C17 C18 -178.4(3) . . . . ?
C15 C16 C17 N4 -178.7(3) . . . . ?
C15 C16 C17 C18 2.1(4) . . . . ?
C19 C18 C17 N4 179.3(3) . . . . ?
C19 C18 C17 C16 -1.6(4) . . . . ?
N1 C22 C23 C24 -178.9(3) . . . . ?
C27 C22 C23 C24 0.6(4) . . . . ?
C19 N3 C15 C16 0.8(5) . . . . ?
C17 C16 C15 N3 -1.9(5) . . . . ?
N2 C27 C26 C25 179.1(3) . . . . ?
C22 C27 C26 C25 -0.6(4) . . . . ?
C15 N3 C19 C18 -0.2(5) . . . . ?
C17 C18 C19 N3 0.7(5) . . . . ?
C27 C26 C25 C24 0.2(5) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C33 C32 C31 C30 0.0(5) . . . . ?
C29 C30 C31 C32 0.0(5) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C26 C25 C24 C23 0.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4O O1 0.84 1.89 2.711(3) 166.1 2_556
O1 H1O N3 0.84 1.79 2.623(4) 169.5 2_556
O3 H3O N1 0.84 1.93 2.755(3) 168.7 .
O2 H2O O3 0.84 1.96 2.784(3) 166.1 2_666
C29 H29 O2 0.95 2.60 3.434(4) 147.3 .
O4 H4O O1 0.84 1.89 2.711(3) 166.1 2_556
O1 H1O N3 0.84 1.79 2.623(4) 169.5 2_556
O3 H3O N1 0.84 1.93 2.755(3) 168.7 .
O2 H2O O3 0.84 1.96 2.784(3) 166.1 2_666
C29 H29 O2 0.95 2.60 3.434(4) 147.3 .

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060889'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H48 N6 O4'
_chemical_formula_weight         628.80

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.7071(19)
_cell_length_b                   8.9632(19)
_cell_length_c                   12.790(2)
_cell_angle_alpha                78.86(4)
_cell_angle_beta                 79.56(4)
_cell_angle_gamma                83.81(4)
_cell_volume                     850.1(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8736
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.645
_diffrn_reflns_theta_max         27.831
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3961
_reflns_number_gt                2677
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1164P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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
H1O H 0.216(4) 0.816(4) 0.921(3) 0.082(9) Uiso 1 1 d . . . . .
H2O H 0.113(4) 0.352(3) 0.647(3) 0.075(9) Uiso 1 1 d . . . . .
O1 O 0.13274(19) 0.76049(16) 0.90960(11) 0.0416(4) Uani 1 1 d . . . . .
N1 N 0.3777(2) 0.91891(16) 0.97335(11) 0.0308(4) Uani 1 1 d . . . . .
O2 O 0.04323(19) 0.40951(16) 0.69913(12) 0.0428(4) Uani 1 1 d . . . . .
C2 C 0.0896(2) 0.58495(19) 0.80431(14) 0.0322(4) Uani 1 1 d . . . . .
C3 C 0.1530(3) 0.50499(19) 0.72055(15) 0.0337(4) Uani 1 1 d . . . . .
C9 C 0.5040(2) 0.84658(19) 1.02712(14) 0.0297(4) Uani 1 1 d . . . . .
C8 C 0.3706(2) 1.07178(19) 0.94575(13) 0.0309(4) Uani 1 1 d . . . . .
C6 C 0.3692(3) 0.7011(2) 0.77023(16) 0.0380(4) Uani 1 1 d . . . . .
H6 H 0.4430 0.7680 0.7874 0.046 Uiso 1 1 calc R U . . .
C7 C -0.0930(3) 0.5646(2) 0.86724(17) 0.0424(5) Uani 1 1 d . . . . .
H7A H -0.1734 0.5536 0.8184 0.064 Uiso 1 1 calc R U . . .
H7B H -0.1345 0.6539 0.9012 0.064 Uiso 1 1 calc R U . . .
H7C H -0.0905 0.4731 0.9232 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1999(2) 0.6831(2) 0.82774(14) 0.0326(4) Uani 1 1 d . . . . .
C4 C 0.3224(3) 0.5228(2) 0.66165(16) 0.0390(4) Uani 1 1 d . . . . .
H4 H 0.3645 0.4684 0.6041 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4287(3) 0.6202(2) 0.68762(17) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.5447 0.6316 0.6479 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5027(3) 0.6768(2) 1.05820(17) 0.0408(5) Uani 1 1 d . . . . .
H10A H 0.4524 0.6498 1.1348 0.061 Uiso 1 1 calc R U . . .
H10B H 0.6240 0.6305 1.0456 0.061 Uiso 1 1 calc R U . . .
H10C H 0.4308 0.6390 1.0145 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2250(3) 1.1482(2) 0.88697(18) 0.0449(5) Uani 1 1 d . . . . .
H11A H 0.1559 1.0708 0.8729 0.067 Uiso 1 1 calc R U . . .
H11B H 0.2758 1.2093 0.8183 0.067 Uiso 1 1 calc R U . . .
H11C H 0.1478 1.2146 0.9312 0.067 Uiso 1 1 calc R U . . .
N2 N 0.1823(2) 0.2254(2) 0.56023(15) 0.0470(4) Uani 1 1 d . . . . .
C14 C 0.2146(2) 0.0192(2) 0.41443(15) 0.0363(4) Uani 1 1 d . . . . .
N3 N 0.2254(3) -0.0811(2) 0.34629(15) 0.0485(5) Uani 1 1 d . . . . .
C15 C 0.2699(3) -0.0223(2) 0.51593(17) 0.0417(5) Uani 1 1 d . . . . .
H15 H 0.3199 -0.1226 0.5380 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2512(3) 0.0823(3) 0.58210(18) 0.0468(5) Uani 1 1 d . . . . .
H16 H 0.2907 0.0507 0.6497 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1440(3) 0.1700(2) 0.38994(17) 0.0427(5) Uani 1 1 d . . . . .
H13 H 0.1055 0.2063 0.3225 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1306(3) 0.2648(2) 0.46312(19) 0.0473(5) Uani 1 1 d . . . . .
H12 H 0.0810 0.3660 0.4440 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1700(4) -0.0329(3) 0.24166(18) 0.0597(6) Uani 1 1 d . . . . .
H18A H 0.0524 0.0213 0.2506 0.090 Uiso 1 1 calc R U . . .
H18B H 0.1657 -0.1225 0.2091 0.090 Uiso 1 1 calc R U . . .
H18C H 0.2546 0.0351 0.1946 0.090 Uiso 1 1 calc R U . . .
C17 C 0.3054(3) -0.2341(3) 0.3711(2) 0.0599(7) Uani 1 1 d . . . . .
H17A H 0.4331 -0.2307 0.3670 0.090 Uiso 1 1 calc R U . . .
H17B H 0.2837 -0.2941 0.3189 0.090 Uiso 1 1 calc R U . . .
H17C H 0.2537 -0.2815 0.4441 0.090 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 1.361(2) . ?
O1 H1O 0.90(3) . ?
N1 C9 1.332(2) . ?
N1 C8 1.345(2) . ?
O2 C3 1.362(2) . ?
O2 H2O 0.97(3) . ?
C2 C3 1.390(3) . ?
C2 C1 1.394(3) . ?
C2 C7 1.500(3) . ?
C3 C4 1.393(3) . ?
C9 C8 1.401(2) 2_677 ?
C9 C10 1.497(2) . ?
C8 C9 1.401(2) 2_677 ?
C8 C11 1.495(3) . ?
C6 C5 1.379(3) . ?
C6 C1 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N2 C16 1.332(3) . ?
N2 C12 1.344(3) . ?
C14 N3 1.354(3) . ?
C14 C13 1.401(3) . ?
C14 C15 1.409(3) . ?
N3 C17 1.443(3) . ?
N3 C18 1.450(3) . ?
C15 C16 1.360(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C13 C12 1.364(3) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 110(2) . . ?
C9 N1 C8 119.39(15) . . ?
C3 O2 H2O 106.8(17) . . ?
C3 C2 C1 118.26(17) . . ?
C3 C2 C7 120.24(16) . . ?
C1 C2 C7 121.50(17) . . ?
O2 C3 C2 117.31(17) . . ?
O2 C3 C4 121.93(17) . . ?
C2 C3 C4 120.76(17) . . ?
N1 C9 C8 120.59(15) . 2_677 ?
N1 C9 C10 117.08(16) . . ?
C8 C9 C10 122.32(16) 2_677 . ?
N1 C8 C9 120.03(16) . 2_677 ?
N1 C8 C11 117.51(16) . . ?
C9 C8 C11 122.46(16) 2_677 . ?
C5 C6 C1 118.93(18) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C1 C6 121.87(17) . . ?
O1 C1 C2 116.59(16) . . ?
C6 C1 C2 121.54(17) . . ?
C5 C4 C3 119.43(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 121.08(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 N2 C12 114.77(18) . . ?
N3 C14 C13 122.31(18) . . ?
N3 C14 C15 122.22(18) . . ?
C13 C14 C15 115.45(18) . . ?
C14 N3 C17 121.40(18) . . ?
C14 N3 C18 120.45(19) . . ?
C17 N3 C18 117.94(19) . . ?
C16 C15 C14 119.48(19) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N2 C16 C15 125.6(2) . . ?
N2 C16 H16 117.2 . . ?
C15 C16 H16 117.2 . . ?
C12 C13 C14 119.93(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
N2 C12 C13 124.79(19) . . ?
N2 C12 H12 117.6 . . ?
C13 C12 H12 117.6 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 O2 179.89(15) . . . . ?
C7 C2 C3 O2 0.0(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C7 C2 C3 C4 -179.91(17) . . . . ?
C8 N1 C9 C8 -0.4(3) . . . 2_677 ?
C8 N1 C9 C10 178.48(16) . . . . ?
C9 N1 C8 C9 0.4(3) . . . 2_677 ?
C9 N1 C8 C11 -179.08(16) . . . . ?
C5 C6 C1 O1 -179.48(17) . . . . ?
C5 C6 C1 C2 0.3(3) . . . . ?
C3 C2 C1 O1 179.43(15) . . . . ?
C7 C2 C1 O1 -0.7(3) . . . . ?
C3 C2 C1 C6 -0.4(3) . . . . ?
C7 C2 C1 C6 179.47(17) . . . . ?
O2 C3 C4 C5 -179.39(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C13 C14 N3 C17 177.4(2) . . . . ?
C15 C14 N3 C17 -4.2(3) . . . . ?
C13 C14 N3 C18 2.7(3) . . . . ?
C15 C14 N3 C18 -178.9(2) . . . . ?
N3 C14 C15 C16 -178.16(19) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C12 N2 C16 C15 -0.8(3) . . . . ?
C14 C15 C16 N2 0.5(3) . . . . ?
N3 C14 C13 C12 177.70(19) . . . . ?
C15 C14 C13 C12 -0.8(3) . . . . ?
C16 N2 C12 C13 0.2(3) . . . . ?
C14 C13 C12 N2 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O N2 0.97(3) 1.72(3) 2.663(2) 164(3) .

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060890'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N2 O2'
_chemical_formula_weight         347.42

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.287(6)
_cell_length_b                   9.179(7)
_cell_length_c                   14.419(11)
_cell_angle_alpha                105.567(19)
_cell_angle_beta                 90.12(3)
_cell_angle_gamma                93.375(19)
_cell_volume                     927.3(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             370
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9785
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.466
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4244
_reflns_number_gt                2190
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1753P)²]
 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         4244
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2921
_refine_ls_wR_factor_gt          0.1922
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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 0.3945(3) 0.7512(2) 0.08980(15) 0.0367(5) Uani 1 1 d . . . . .
H1 H 0.3195 0.8118 0.0801 0.055 Uiso 1 1 calc R U . . .
N1 N 0.1338(3) 0.9151(2) 0.02399(16) 0.0282(5) Uani 1 1 d . . . . .
O2 O 0.4962(3) 0.4270(2) 0.28660(15) 0.0342(5) Uani 1 1 d . . . . .
H2 H 0.4504 0.3987 0.3328 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0236(4) 0.8466(3) -0.02090(18) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.3823(4) 0.5219(3) 0.25998(19) 0.0273(6) Uani 1 1 d . . . . .
C1 C 0.3302(4) 0.6882(3) 0.16064(18) 0.0270(6) Uani 1 1 d . . . . .
C9 C 0.1590(4) 1.0674(3) 0.04471(18) 0.0266(6) Uani 1 1 d . . . . .
C2 C 0.4425(4) 0.5869(3) 0.18705(18) 0.0258(6) Uani 1 1 d . . . . .
C10 C -0.0455(4) 0.6780(3) -0.0427(2) 0.0350(7) Uani 1 1 d . . . . .
H10A H -0.0451 0.6337 -0.1125 0.053 Uiso 1 1 calc R U . . .
H10B H -0.1621 0.6485 -0.0170 0.053 Uiso 1 1 calc R U . . .
H10C H 0.0565 0.6410 -0.0127 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1614(4) 0.7228(3) 0.2037(2) 0.0320(6) Uani 1 1 d . . . . .
H6 H 0.0864 0.7913 0.1847 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2129(4) 0.5554(3) 0.3041(2) 0.0338(7) Uani 1 1 d . . . . .
H4 H 0.1726 0.5103 0.3532 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1051(4) 0.6549(4) 0.2752(2) 0.0359(7) Uani 1 1 d . . . . .
H5 H -0.0100 0.6774 0.3048 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6223(4) 0.5472(4) 0.1380(2) 0.0362(7) Uani 1 1 d . . . . .
H7A H 0.6729 0.4648 0.1593 0.054 Uiso 1 1 calc R U . . .
H7B H 0.7093 0.6363 0.1546 0.054 Uiso 1 1 calc R U . . .
H7C H 0.6018 0.5148 0.0680 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3359(5) 1.1376(4) 0.0919(3) 0.0430(8) Uani 1 1 d . . . . .
H11A H 0.4071 1.0596 0.1074 0.065 Uiso 1 1 calc R U . . .
H11B H 0.3114 1.2152 0.1513 0.065 Uiso 1 1 calc R U . . .
H11C H 0.4059 1.1842 0.0482 0.065 Uiso 1 1 calc R U . . .
N2 N 0.3501(4) 0.2671(3) 0.40624(19) 0.0400(6) Uani 1 1 d . . . . .
C14 C 0.2764(4) 0.0815(3) 0.5320(2) 0.0284(6) Uani 1 1 d . . . . .
C17 C 0.2382(4) -0.0159(3) 0.5983(2) 0.0319(6) Uani 1 1 d . . . . .
C13 C 0.2782(5) 0.0224(3) 0.4329(2) 0.0396(7) Uani 1 1 d . . . . .
H13 H 0.2555 -0.0834 0.4055 0.047 Uiso 1 1 calc R U . . .
C20 C 0.1702(5) -0.1991(5) 0.7241(3) 0.0586(11) Uani 1 1 d . . . . .
H20 H 0.1471 -0.2615 0.7663 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3157(4) 0.2386(3) 0.5662(2) 0.0374(7) Uani 1 1 d . . . . .
H15 H 0.3198 0.2861 0.6335 0.045 Uiso 1 1 calc R U . . .
C22 C 0.2667(5) 0.0421(4) 0.6982(2) 0.0472(8) Uani 1 1 d . . . . .
H22 H 0.3108 0.1446 0.7238 0.057 Uiso 1 1 calc R U . . .
C16 C 0.3484(5) 0.3239(4) 0.5012(3) 0.0436(8) Uani 1 1 d . . . . .
H16 H 0.3711 0.4303 0.5263 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1759(5) -0.1666(4) 0.5637(3) 0.0433(8) Uani 1 1 d . . . . .
H18 H 0.1549 -0.2085 0.4965 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3131(5) 0.1170(4) 0.3735(2) 0.0449(8) Uani 1 1 d . . . . .
H12 H 0.3106 0.0730 0.3058 0.054 Uiso 1 1 calc R U . . .
C21 C 0.2308(6) -0.0491(5) 0.7601(3) 0.0586(11) Uani 1 1 d . . . . .
H21 H 0.2483 -0.0077 0.8275 0.070 Uiso 1 1 calc R U . . .
C19 C 0.1437(6) -0.2570(4) 0.6263(3) 0.0565(10) Uani 1 1 d . . . . .
H19 H 0.1028 -0.3604 0.6010 0.068 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 1.372(3) . ?
O1 H1 0.8400 . ?
N1 C9 1.350(3) . ?
N1 C8 1.350(4) . ?
O2 C3 1.363(3) . ?
O2 H2 0.8400 . ?
C8 C9 1.397(4) 2_575 ?
C8 C10 1.493(4) . ?
C3 C4 1.402(4) . ?
C3 C2 1.401(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.399(4) . ?
C9 C8 1.397(4) 2_575 ?
C9 C11 1.484(4) . ?
C2 C7 1.508(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 C5 1.391(4) . ?
C6 H6 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N2 C16 1.328(5) . ?
N2 C12 1.342(4) . ?
C14 C13 1.386(4) . ?
C14 C15 1.404(4) . ?
C14 C17 1.490(4) . ?
C17 C18 1.387(4) . ?
C17 C22 1.405(5) . ?
C13 C12 1.388(4) . ?
C13 H13 0.9500 . ?
C20 C19 1.377(6) . ?
C20 C21 1.380(6) . ?
C20 H20 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C22 C21 1.393(5) . ?
C22 H22 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C21 H21 0.9500 . ?
C19 H19 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
C1 O1 H1 109.5 . . ?
C9 N1 C8 119.1(2) . . ?
C3 O2 H2 109.5 . . ?
N1 C8 C9 120.3(2) . 2_575 ?
N1 C8 C10 117.3(2) . . ?
C9 C8 C10 122.4(3) 2_575 . ?
O2 C3 C4 121.9(2) . . ?
O2 C3 C2 117.2(2) . . ?
C4 C3 C2 120.9(2) . . ?
O1 C1 C6 121.8(2) . . ?
O1 C1 C2 116.5(2) . . ?
C6 C1 C2 121.7(2) . . ?
N1 C9 C8 120.6(2) . 2_575 ?
N1 C9 C11 117.3(2) . . ?
C8 C9 C11 122.1(2) 2_575 . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 C7 121.2(2) . . ?
C3 C2 C7 120.7(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 N2 C12 116.1(3) . . ?
C13 C14 C15 115.8(3) . . ?
C13 C14 C17 122.1(3) . . ?
C15 C14 C17 122.1(3) . . ?
C18 C17 C22 117.8(3) . . ?
C18 C17 C14 121.4(3) . . ?
C22 C17 C14 120.8(3) . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C19 C20 C21 119.1(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
N2 C16 C15 124.4(3) . . ?
N2 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
N2 C12 C13 123.6(3) . . ?
N2 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C8 C9 -0.6(4) . . . 2_575 ?
C9 N1 C8 C10 179.8(2) . . . . ?
C8 N1 C9 C8 0.6(4) . . . 2_575 ?
C8 N1 C9 C11 -178.5(3) . . . . ?
O1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
O1 C1 C2 C7 -1.4(4) . . . . ?
C6 C1 C2 C7 178.3(3) . . . . ?
O2 C3 C2 C1 -178.1(2) . . . . ?
C4 C3 C2 C1 1.1(4) . . . . ?
O2 C3 C2 C7 2.5(4) . . . . ?
C4 C3 C2 C7 -178.3(3) . . . . ?
O1 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
O2 C3 C4 C5 178.7(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C1 C6 C5 C4 0.3(4) . . . . ?
C13 C14 C17 C18 -9.8(4) . . . . ?
C15 C14 C17 C18 171.3(3) . . . . ?
C13 C14 C17 C22 169.5(3) . . . . ?
C15 C14 C17 C22 -9.5(4) . . . . ?
C15 C14 C13 C12 -1.4(5) . . . . ?
C17 C14 C13 C12 179.6(3) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C17 C14 C15 C16 -179.4(3) . . . . ?
C18 C17 C22 C21 -0.8(5) . . . . ?
C14 C17 C22 C21 180.0(3) . . . . ?
C12 N2 C16 C15 1.6(5) . . . . ?
C14 C15 C16 N2 -1.8(5) . . . . ?
C22 C17 C18 C19 -0.3(5) . . . . ?
C14 C17 C18 C19 178.9(3) . . . . ?
C16 N2 C12 C13 -1.3(5) . . . . ?
C14 C13 C12 N2 1.4(5) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C17 C22 C21 C20 1.3(6) . . . . ?
C21 C20 C19 C18 -0.4(6) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.84 1.92 2.729(3) 160.1 .
O1 H1 N1 0.84 1.99 2.805(3) 164.9 .
C11 H11B O2 0.98 2.65 3.453(4) 138.9 1_565
C11 H11C O1 0.98 2.64 3.604(4) 167.6 2_675
O2 H2 N2 0.84 1.92 2.729(3) 160.1 .
O1 H1 N1 0.84 1.99 2.805(3) 164.9 .
C11 H11B O2 0.98 2.65 3.453(4) 138.9 1_565
C11 H11C O1 0.98 2.64 3.604(4) 167.6 2_675

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.172

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060891'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N4 O2'
_chemical_formula_weight         404.50

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.635(5)
_cell_length_b                   9.055(8)
_cell_length_c                   17.237(13)
_cell_angle_alpha                96.22(3)
_cell_angle_beta                 94.09(2)
_cell_angle_gamma                113.734(15)
_cell_volume                     1075.8(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10143
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.198
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4226
_reflns_number_gt                3610
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1041P)²+0.1835P]
 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         4226
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001

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 0.54172(18) 0.78903(16) 0.18585(7) 0.0379(3) Uani 1 1 d . . . . .
H1 H 0.6053 0.8523 0.1559 0.057 Uiso 1 1 calc R U . . .
O2 O 0.59164(18) 0.43717(15) 0.35915(7) 0.0354(3) Uani 1 1 d . . . . .
H2 H 0.6638 0.3934 0.3742 0.053 Uiso 1 1 calc R U . . .
N1 N 0.7340(2) 0.98237(17) 0.07514(8) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.8960(2) 1.18151(18) -0.03807(8) 0.0323(3) Uani 1 1 d . . . . .
C2 C 0.5692(2) 0.61421(18) 0.27298(8) 0.0258(4) Uani 1 1 d . . . . .
C23 C 0.8718(2) 1.1300(2) 0.09568(10) 0.0297(4) Uani 1 1 d . . . . .
C1 C 0.6482(2) 0.71367(19) 0.21662(9) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.6745(2) 0.53579(19) 0.30595(9) 0.0264(3) Uani 1 1 d . . . . .
C15 C 0.6717(2) 0.92699(19) -0.00345(10) 0.0280(4) Uani 1 1 d . . . . .
C16 C 0.5260(3) 0.7685(2) -0.02816(11) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.4704 0.7003 0.0097 0.042 Uiso 1 1 calc R U . . .
C6 C 0.8262(2) 0.7339(2) 0.19337(9) 0.0296(4) Uani 1 1 d . . . . .
H6 H 0.8775 0.8008 0.1545 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8552(2) 0.55751(19) 0.28392(9) 0.0288(4) Uani 1 1 d . . . . .
H4 H 0.9270 0.5056 0.3075 0.035 Uiso 1 1 calc R U . . .
C22 C 0.9551(2) 1.2317(2) 0.03707(10) 0.0304(4) Uani 1 1 d . . . . .
C19 C 0.6841(3) 0.9687(2) -0.14061(10) 0.0374(4) Uani 1 1 d . . . . .
H19 H 0.7354 1.0365 -0.1791 0.045 Uiso 1 1 calc R U . . .
N4 N 0.7633(2) -0.10258(18) 0.55330(9) 0.0362(4) Uani 1 1 d . . . . .
C20 C 0.7526(2) 1.0280(2) -0.06027(10) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.7196(3) -0.0172(2) 0.42759(10) 0.0347(4) Uani 1 1 d . . . . .
H9 H 0.6936 -0.1216 0.3997 0.042 Uiso 1 1 calc R U . . .
N3 N 0.7526(2) 0.2571(2) 0.42096(10) 0.0450(4) Uani 1 1 d . . . . .
C5 C 0.9279(2) 0.6555(2) 0.22741(10) 0.0307(4) Uani 1 1 d . . . . .
H5 H 1.0496 0.6694 0.2117 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7619(2) 0.0134(2) 0.51031(9) 0.0278(4) Uani 1 1 d . . . . .
C7 C 0.3740(2) 0.5896(2) 0.29619(10) 0.0359(4) Uani 1 1 d . . . . .
H7A H 0.3524 0.5339 0.3426 0.054 Uiso 1 1 calc R U . . .
H7B H 0.2740 0.5231 0.2526 0.054 Uiso 1 1 calc R U . . .
H7C H 0.3686 0.6958 0.3085 0.054 Uiso 1 1 calc R U . . .
C21 C 1.1125(3) 1.3998(2) 0.06163(12) 0.0437(5) Uani 1 1 d . . . . .
H21A H 1.1606 1.4471 0.0148 0.066 Uiso 1 1 calc R U . . .
H21B H 1.2182 1.3931 0.0947 0.066 Uiso 1 1 calc R U . . .
H21C H 1.0615 1.4687 0.0914 0.066 Uiso 1 1 calc R U . . .
C24 C 0.9396(3) 1.1908(2) 0.18129(10) 0.0417(4) Uani 1 1 d . . . . .
H24A H 0.8708 1.1050 0.2120 0.063 Uiso 1 1 calc R U . . .
H24B H 0.9142 1.2870 0.1967 0.063 Uiso 1 1 calc R U . . .
H24C H 1.0784 1.2203 0.1913 0.063 Uiso 1 1 calc R U . . .
C18 C 0.5445(3) 0.8143(2) -0.16334(11) 0.0397(4) Uani 1 1 d . . . . .
H18 H 0.5008 0.7747 -0.2176 0.048 Uiso 1 1 calc R U . . .
C17 C 0.4648(3) 0.7131(2) -0.10668(11) 0.0393(4) Uani 1 1 d . . . . .
H17 H 0.3681 0.6058 -0.1231 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8028(2) 0.1739(2) 0.54563(10) 0.0339(4) Uani 1 1 d . . . . .
H11 H 0.8351 0.2039 0.6010 0.041 Uiso 1 1 calc R U . . .
C13 C 0.8030(3) -0.0670(3) 0.63840(11) 0.0455(5) Uani 1 1 d . . . . .
H13A H 0.9348 0.0163 0.6538 0.068 Uiso 1 1 calc R U . . .
H13B H 0.7892 -0.1666 0.6597 0.068 Uiso 1 1 calc R U . . .
H13C H 0.7116 -0.0268 0.6592 0.068 Uiso 1 1 calc R U . . .
C8 C 0.7163(3) 0.1054(3) 0.38767(11) 0.0421(5) Uani 1 1 d . . . . .
H8 H 0.6858 0.0805 0.3321 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7956(3) 0.2862(2) 0.49962(12) 0.0405(4) Uani 1 1 d . . . . .
H12 H 0.8232 0.3928 0.5253 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7152(3) -0.2679(2) 0.51560(12) 0.0429(5) Uani 1 1 d . . . . .
H14A H 0.5838 -0.3142 0.4879 0.064 Uiso 1 1 calc R U . . .
H14B H 0.7233 -0.3348 0.5556 0.064 Uiso 1 1 calc R U . . .
H14C H 0.8061 -0.2662 0.4779 0.064 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 1.368(2) . ?
O1 H1 0.8400 . ?
O2 C3 1.358(2) . ?
O2 H2 0.8400 . ?
N1 C23 1.316(2) . ?
N1 C15 1.372(2) . ?
N2 C22 1.308(2) . ?
N2 C20 1.370(2) . ?
C2 C1 1.398(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.506(2) . ?
C23 C22 1.447(2) . ?
C23 C24 1.495(3) . ?
C1 C6 1.391(2) . ?
C3 C4 1.400(2) . ?
C15 C16 1.412(3) . ?
C15 C20 1.416(2) . ?
C16 C17 1.370(3) . ?
C16 H16 0.9500 . ?
C6 C5 1.386(2) . ?
C6 H6 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C22 C21 1.502(3) . ?
C19 C18 1.366(3) . ?
C19 C20 1.410(3) . ?
C19 H19 0.9500 . ?
N4 C10 1.352(2) . ?
N4 C13 1.450(3) . ?
N4 C14 1.453(3) . ?
C9 C8 1.375(3) . ?
C9 C10 1.411(3) . ?
C9 H9 0.9500 . ?
N3 C8 1.339(3) . ?
N3 C12 1.344(3) . ?
C5 H5 0.9500 . ?
C10 C11 1.413(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C18 C17 1.412(3) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
C23 N1 C15 118.22(14) . . ?
C22 N2 C20 117.99(15) . . ?
C1 C2 C3 118.21(15) . . ?
C1 C2 C7 120.78(14) . . ?
C3 C2 C7 121.00(14) . . ?
N1 C23 C22 121.00(16) . . ?
N1 C23 C24 118.33(15) . . ?
C22 C23 C24 120.67(16) . . ?
O1 C1 C6 122.15(14) . . ?
O1 C1 C2 116.66(14) . . ?
C6 C1 C2 121.20(14) . . ?
O2 C3 C4 122.25(14) . . ?
O2 C3 C2 116.71(15) . . ?
C4 C3 C2 121.03(14) . . ?
N1 C15 C16 120.10(15) . . ?
N1 C15 C20 120.35(15) . . ?
C16 C15 C20 119.55(16) . . ?
C17 C16 C15 120.00(16) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C5 C6 C1 119.33(15) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C4 C3 119.11(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N2 C22 C23 121.61(16) . . ?
N2 C22 C21 118.15(16) . . ?
C23 C22 C21 120.24(16) . . ?
C18 C19 C20 120.36(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C10 N4 C13 120.75(16) . . ?
C10 N4 C14 120.74(16) . . ?
C13 N4 C14 118.44(15) . . ?
N2 C20 C19 120.03(15) . . ?
N2 C20 C15 120.82(16) . . ?
C19 C20 C15 119.15(16) . . ?
C8 C9 C10 119.51(17) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C8 N3 C12 115.05(15) . . ?
C4 C5 C6 121.10(15) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N4 C10 C9 122.55(16) . . ?
N4 C10 C11 121.92(16) . . ?
C9 C10 C11 115.53(15) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C18 C17 120.47(17) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C17 C18 120.45(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C12 C11 C10 119.71(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C8 C9 125.18(18) . . ?
N3 C8 H8 117.4 . . ?
C9 C8 H8 117.4 . . ?
N3 C12 C11 125.01(19) . . ?
N3 C12 H12 117.5 . . ?
C11 C12 H12 117.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C23 C22 0.2(2) . . . . ?
C15 N1 C23 C24 179.83(14) . . . . ?
C3 C2 C1 O1 -179.73(14) . . . . ?
C7 C2 C1 O1 1.5(2) . . . . ?
C3 C2 C1 C6 0.4(2) . . . . ?
C7 C2 C1 C6 -178.37(15) . . . . ?
C1 C2 C3 O2 -178.53(13) . . . . ?
C7 C2 C3 O2 0.2(2) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C7 C2 C3 C4 179.45(15) . . . . ?
C23 N1 C15 C16 179.12(14) . . . . ?
C23 N1 C15 C20 -0.9(2) . . . . ?
N1 C15 C16 C17 -179.59(14) . . . . ?
C20 C15 C16 C17 0.4(2) . . . . ?
O1 C1 C6 C5 179.32(15) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
O2 C3 C4 C5 177.83(14) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C20 N2 C22 C23 -0.5(2) . . . . ?
C20 N2 C22 C21 179.88(15) . . . . ?
N1 C23 C22 N2 0.5(2) . . . . ?
C24 C23 C22 N2 -179.10(15) . . . . ?
N1 C23 C22 C21 -179.87(15) . . . . ?
C24 C23 C22 C21 0.5(2) . . . . ?
C22 N2 C20 C19 179.95(14) . . . . ?
C22 N2 C20 C15 -0.2(2) . . . . ?
C18 C19 C20 N2 178.37(16) . . . . ?
C18 C19 C20 C15 -1.5(3) . . . . ?
N1 C15 C20 N2 0.9(2) . . . . ?
C16 C15 C20 N2 -179.10(14) . . . . ?
N1 C15 C20 C19 -179.24(14) . . . . ?
C16 C15 C20 C19 0.7(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C13 N4 C10 C9 -178.48(16) . . . . ?
C14 N4 C10 C9 -1.8(3) . . . . ?
C13 N4 C10 C11 1.5(3) . . . . ?
C14 N4 C10 C11 178.19(15) . . . . ?
C8 C9 C10 N4 178.49(16) . . . . ?
C8 C9 C10 C11 -1.5(2) . . . . ?
C20 C19 C18 C17 1.0(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C19 C18 C17 C16 0.2(3) . . . . ?
N4 C10 C11 C12 -178.67(16) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C12 N3 C8 C9 0.2(3) . . . . ?
C10 C9 C8 N3 0.8(3) . . . . ?
C8 N3 C12 C11 -0.4(3) . . . . ?
C10 C11 C12 N3 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N3 0.84 1.86 2.666(2) 161.5 .
O1 H1 N1 0.84 1.98 2.814(2) 173.3 .
O2 H2 N3 0.84 1.86 2.666(2) 161.5 .
O1 H1 N1 0.84 1.98 2.814(2) 173.3 .

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-2

