# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436809'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         424.48

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9476(4)
_cell_length_b                   11.0300(3)
_cell_length_c                   11.0714(3)
_cell_angle_alpha                86.1003(17)
_cell_angle_beta                 64.8281(17)
_cell_angle_gamma                60.6087(15)
_cell_volume                     1037.28(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.2562
_cell_measurement_theta_max      31.0425
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            39746
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         31.19
_diffrn_reflns_theta_full        31.19
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             6681
_reflns_number_gt                5553
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1368
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         6681
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0821P)²+0.2285P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.52102(12) 0.23664(10) -0.01727(10) 0.01184(19) Uani d . . . 1 . .
C C2 0.44198(12) 0.28699(10) 0.13756(10) 0.01053(18) Uani d . . . 1 . .
C C3 0.30530(12) 0.26246(10) 0.18696(10) 0.01057(18) Uani d . . . 1 . .
C C4 0.18580(12) 0.28915(11) 0.31510(10) 0.01319(19) Uani d . . . 1 . .
H H4 0.1746 0.3379 0.3901 0.016 Uiso calc U . R 1 . .
C C5 0.08145(13) 0.24326(11) 0.33273(11) 0.0159(2) Uani d . . . 1 . .
H H5 -0.0016 0.2614 0.4202 0.019 Uiso calc U . R 1 . .
C C6 0.09879(13) 0.17121(12) 0.22284(11) 0.0166(2) Uani d . . . 1 . .
H H6 0.0282 0.1394 0.2367 0.02 Uiso calc U . R 1 . .
C C7 0.21856(13) 0.14458(11) 0.09204(11) 0.0146(2) Uani d . . . 1 . .
H H7 0.23 0.0962 0.0167 0.018 Uiso calc U . R 1 . .
C C8 0.31938(12) 0.19178(10) 0.07733(10) 0.01080(18) Uani d . . . 1 . .
C C9 0.40933(12) 0.43723(10) 0.17343(10) 0.01106(18) Uani d . . . 1 . .
H H9 0.4845 0.454 0.0937 0.013 Uiso calc U . R 1 . .
C C10 0.45390(12) 0.42539(10) 0.28877(10) 0.01294(19) Uani d . . . 1 . .
H H10A 0.5124 0.4742 0.2782 0.016 Uiso calc U . R 1 . .
H H10B 0.36 0.4645 0.3782 0.016 Uiso calc U . R 1 . .
C C11 0.55688(12) 0.26723(10) 0.27163(10) 0.01100(18) Uani d . . . 1 . .
C C12 0.65252(12) 0.20212(10) 0.34503(10) 0.01121(18) Uani d . . . 1 . .
C C13 0.76282(13) 0.05728(11) 0.31219(11) 0.0160(2) Uani d . . . 1 . .
H H13 0.7823 0.0012 0.2375 0.019 Uiso calc U . R 1 . .
C C14 0.84414(14) -0.00517(12) 0.38820(12) 0.0187(2) Uani d . . . 1 . .
H H14 0.9188 -0.1037 0.3655 0.022 Uiso calc U . R 1 . .
C C15 0.81629(13) 0.07651(12) 0.49733(11) 0.0158(2) Uani d . . . 1 . .
H H15 0.8697 0.0333 0.5508 0.019 Uiso calc U . R 1 . .
C C16 0.71083(13) 0.22094(12) 0.52833(11) 0.0166(2) Uani d . . . 1 . .
H H16 0.6939 0.2771 0.6015 0.02 Uiso calc U . R 1 . .
C C17 0.62978(13) 0.28348(11) 0.45204(11) 0.0154(2) Uani d . . . 1 . .
H H17 0.5582 0.3826 0.473 0.019 Uiso calc U . R 1 . .
C C18 0.24492(12) 0.55313(10) 0.20301(10) 0.01248(19) Uani d . . . 1 . .
C C19 0.07655(13) 0.66511(12) 0.09539(11) 0.0170(2) Uani d . . . 1 . .
H H19A -0.0011 0.7121 0.1905 0.02 Uiso calc U . R 1 . .
H H19B 0.0357 0.6216 0.0592 0.02 Uiso calc U . R 1 . .
C C20 0.10058(15) 0.77166(14) 0.01227(14) 0.0254(3) Uani d . . . 1 . .
H H20A 0.1404 0.8147 0.0489 0.038 Uiso calc U . R 1 . .
H H20B 0.0004 0.8452 0.0154 0.038 Uiso calc U . R 1 . .
H H20C 0.1767 0.7247 -0.0819 0.038 Uiso calc U . R 1 . .
C C21 0.49256(12) 0.11599(11) -0.17622(10) 0.01316(19) Uani d . . . 1 . .
H H21A 0.4869 0.0288 -0.1712 0.016 Uiso calc U . R 1 . .
H H21B 0.6029 0.0889 -0.2364 0.016 Uiso calc U . R 1 . .
C C22 0.38990(12) 0.21521(11) -0.23880(10) 0.01206(19) Uani d . . . 1 . .
C C23 0.30477(13) 0.36132(11) -0.19823(11) 0.0161(2) Uani d . . . 1 . .
H H23 0.3072 0.4018 -0.1269 0.019 Uiso calc U . R 1 . .
C C24 0.21591(14) 0.44839(12) -0.26195(12) 0.0185(2) Uani d . . . 1 . .
H H24 0.1582 0.5481 -0.2341 0.022 Uiso calc U . R 1 . .
C C25 0.21148(13) 0.38977(12) -0.36617(11) 0.0178(2) Uani d . . . 1 . .
H H25 0.1503 0.4491 -0.4092 0.021 Uiso calc U . R 1 . .
C C26 0.29698(13) 0.24394(12) -0.40710(11) 0.0175(2) Uani d . . . 1 . .
H H26 0.2949 0.2035 -0.4788 0.021 Uiso calc U . R 1 . .
C C27 0.38545(13) 0.15722(11) -0.34354(11) 0.0147(2) Uani d . . . 1 . .
H H27 0.4434 0.0575 -0.3718 0.018 Uiso calc U . R 1 . .
N N1 0.44929(10) 0.17554(9) -0.04179(8) 0.01140(17) Uani d . . . 1 . .
N N2 0.55265(10) 0.19212(9) 0.19105(9) 0.01156(17) Uani d . . . 1 . .
O O1 0.62783(9) 0.24917(9) -0.10249(8) 0.01784(17) Uani d . . . 1 . .
O O2 0.14515(10) 0.62874(9) 0.31105(8) 0.01981(18) Uani d . . . 1 . .
O O3 0.22614(9) 0.55636(8) 0.09031(8) 0.01494(16) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2161(13) ?
C1 N1 . 1.3676(13) ?
C1 C2 . 1.5465(14) ?
C2 N2 . 1.4816(13) ?
C2 C3 . 1.5141(14) ?
C2 C9 . 1.5553(14) ?
C3 C4 . 1.3824(14) ?
C3 C8 . 1.3987(13) ?
C4 C5 . 1.4013(15) ?
C5 C6 . 1.3909(16) ?
C6 C7 . 1.4026(15) ?
C7 C8 . 1.3839(14) ?
C8 N1 . 1.4074(13) ?
C9 C18 . 1.5093(14) ?
C9 C10 . 1.5267(14) ?
C10 C11 . 1.5110(14) ?
C11 N2 . 1.2875(13) ?
C11 C12 . 1.4761(14) ?
C12 C17 . 1.3948(14) ?
C12 C13 . 1.3981(14) ?
C13 C14 . 1.3900(15) ?
C14 C15 . 1.3890(16) ?
C15 C16 . 1.3859(15) ?
C16 C17 . 1.3906(15) ?
C18 O2 . 1.2040(13) ?
C18 O3 . 1.3437(12) ?
C19 O3 . 1.4583(13) ?
C19 C20 . 1.4992(16) ?
C21 N1 . 1.4487(12) ?
C21 C22 . 1.5141(14) ?
C22 C23 . 1.3913(14) ?
C22 C27 . 1.3914(14) ?
C23 C24 . 1.3932(15) ?
C24 C25 . 1.3900(16) ?
C25 C26 . 1.3889(16) ?
C26 C27 . 1.3882(15) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 125.87(9) ?
O1 C1 C2 . . 126.25(9) ?
N1 C1 C2 . . 107.88(8) ?
N2 C2 C3 . . 109.34(8) ?
N2 C2 C1 . . 108.47(8) ?
C3 C2 C1 . . 101.98(8) ?
N2 C2 C9 . . 105.35(8) ?
C3 C2 C9 . . 119.16(8) ?
C1 C2 C9 . . 112.25(8) ?
C4 C3 C8 . . 119.82(9) ?
C4 C3 C2 . . 131.58(9) ?
C8 C3 C2 . . 108.45(8) ?
C3 C4 C5 . . 119.01(10) ?
C6 C5 C4 . . 120.34(10) ?
C5 C6 C7 . . 121.27(10) ?
C8 C7 C6 . . 117.20(10) ?
C7 C8 C3 . . 122.35(9) ?
C7 C8 N1 . . 127.85(9) ?
C3 C8 N1 . . 109.77(9) ?
C18 C9 C10 . . 115.91(8) ?
C18 C9 C2 . . 113.11(8) ?
C10 C9 C2 . . 103.76(8) ?
C11 C10 C9 . . 101.72(8) ?
N2 C11 C12 . . 121.87(9) ?
N2 C11 C10 . . 115.46(9) ?
C12 C11 C10 . . 122.65(9) ?
C17 C12 C13 . . 118.89(9) ?
C17 C12 C11 . . 120.34(9) ?
C13 C12 C11 . . 120.73(9) ?
C14 C13 C12 . . 120.40(10) ?
C15 C14 C13 . . 119.98(10) ?
C16 C15 C14 . . 120.16(10) ?
C15 C16 C17 . . 119.83(10) ?
C16 C17 C12 . . 120.67(10) ?
O2 C18 O3 . . 125.28(10) ?
O2 C18 C9 . . 125.55(10) ?
O3 C18 C9 . . 109.15(8) ?
O3 C19 C20 . . 109.07(9) ?
N1 C21 C22 . . 113.90(8) ?
C23 C22 C27 . . 119.34(9) ?
C23 C22 C21 . . 122.37(9) ?
C27 C22 C21 . . 118.26(9) ?
C22 C23 C24 . . 120.19(10) ?
C25 C24 C23 . . 120.19(10) ?
C26 C25 C24 . . 119.64(10) ?
C27 C26 C25 . . 120.15(10) ?
C26 C27 C22 . . 120.49(10) ?
C1 N1 C8 . . 111.31(8) ?
C1 N1 C21 . . 123.51(9) ?
C8 N1 C21 . . 124.86(9) ?
C11 N2 C2 . . 109.21(8) ?
C18 O3 C19 . . 118.08(8) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436810'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H24 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         456.52

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3650(9)
_cell_length_b                   11.4265(10)
_cell_length_c                   11.9971(11)
_cell_angle_alpha                74.104(3)
_cell_angle_beta                 80.112(3)
_cell_angle_gamma                71.016(3)
_cell_volume                     1162.72(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2871
_cell_measurement_theta_min      2.3004
_cell_measurement_theta_max      24.9030
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18124
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5770
_reflns_number_gt                3976
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1209
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         5770
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+0.3193P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.24571(19) 0.11954(16) 0.59123(15) 0.0216(4) Uani d . . . 1 . .
H H1 0.2946 0.0519 0.6512 0.026 Uiso calc U . R 1 . .
C C2 0.1566(2) 0.09809(18) 0.52201(16) 0.0270(4) Uani d . . . 1 . .
H H2 0.1455 0.0157 0.5341 0.032 Uiso calc U . R 1 . .
C C3 0.0840(2) 0.19676(18) 0.43543(16) 0.0277(4) Uani d . . . 1 . .
H H3 0.0231 0.1818 0.3883 0.033 Uiso calc U . R 1 . .
C C4 0.0996(2) 0.31694(18) 0.41717(15) 0.0264(4) Uani d . . . 1 . .
H H4 0.0492 0.3844 0.3578 0.032 Uiso calc U . R 1 . .
C C5 0.18904(18) 0.33907(17) 0.48583(14) 0.0207(4) Uani d . . . 1 . .
H H5 0.1995 0.4218 0.4734 0.025 Uiso calc U . R 1 . .
C C6 0.26354(17) 0.24020(15) 0.57292(13) 0.0157(3) Uani d . . . 1 . .
C C7 0.35945(17) 0.26349(15) 0.64577(13) 0.0155(3) Uani d . . . 1 . .
C C8 0.39924(19) 0.38586(15) 0.61893(15) 0.0204(4) Uani d . . . 1 . .
H H8A 0.3072 0.4587 0.6235 0.025 Uiso calc U . R 1 . .
H H8B 0.4533 0.4017 0.5403 0.025 Uiso calc U . R 1 . .
C C9 0.50226(17) 0.36495(15) 0.71317(14) 0.0162(3) Uani d . . . 1 . .
H H9 0.4563 0.4304 0.7601 0.019 Uiso calc U . R 1 . .
C C10 0.66296(18) 0.36638(14) 0.66662(14) 0.0158(3) Uani d . . . 1 . .
C C11 0.75624(18) 0.38921(15) 0.74334(13) 0.0155(3) Uani d . . . 1 . .
C C12 0.91161(18) 0.32544(16) 0.73796(14) 0.0194(4) Uani d . . . 1 . .
H H12 0.9547 0.2708 0.6861 0.023 Uiso calc U . R 1 . .
C C13 1.00239(19) 0.34220(17) 0.80855(15) 0.0223(4) Uani d . . . 1 . .
H H13 1.1071 0.2962 0.8073 0.027 Uiso calc U . R 1 . .
C C14 0.9412(2) 0.42563(16) 0.88088(15) 0.0226(4) Uani d . . . 1 . .
H H14 1.0045 0.4378 0.9281 0.027 Uiso calc U . R 1 . .
C C15 0.7873(2) 0.49181(16) 0.88472(15) 0.0224(4) Uani d . . . 1 . .
H H15 0.7456 0.5502 0.9333 0.027 Uiso calc U . R 1 . .
C C16 0.69487(19) 0.47177(15) 0.81689(14) 0.0187(4) Uani d . . . 1 . .
H H16 0.5893 0.5148 0.8209 0.022 Uiso calc U . R 1 . .
C C17 0.50305(17) 0.22857(14) 0.79185(13) 0.0144(3) Uani d . . . 1 . .
C C18 0.42143(18) 0.24364(15) 0.91342(14) 0.0158(3) Uani d . . . 1 . .
C C19 0.65057(18) 0.09175(15) 0.94492(14) 0.0154(3) Uani d . . . 1 . .
C C20 0.65227(17) 0.12896(14) 0.82377(13) 0.0146(3) Uani d . . . 1 . .
C C21 0.77365(18) 0.06903(15) 0.75562(15) 0.0191(4) Uani d . . . 1 . .
H H21 0.7747 0.0916 0.6732 0.023 Uiso calc U . R 1 . .
C C22 0.89485(19) -0.02544(16) 0.81025(15) 0.0222(4) Uani d . . . 1 . .
H H22 0.9804 -0.0659 0.7646 0.027 Uiso calc U . R 1 . .
C C23 0.89100(19) -0.06053(16) 0.93072(15) 0.0219(4) Uani d . . . 1 . .
H H23 0.974 -0.1254 0.9663 0.026 Uiso calc U . R 1 . .
C C24 0.76826(18) -0.00282(15) 1.00069(15) 0.0190(4) Uani d . . . 1 . .
H H24 0.7655 -0.0274 1.0832 0.023 Uiso calc U . R 1 . .
C C25 0.47221(18) 0.14797(16) 1.12051(13) 0.0180(3) Uani d . . . 1 . .
H H25A 0.4923 0.0561 1.1577 0.022 Uiso calc U . R 1 . .
H H25B 0.3618 0.1887 1.1331 0.022 Uiso calc U . R 1 . .
C C26 0.55454(17) 0.20410(15) 1.18062(14) 0.0155(3) Uani d . . . 1 . .
C C27 0.66121(18) 0.26619(16) 1.12264(15) 0.0200(4) Uani d . . . 1 . .
H H27 0.683 0.2771 1.0408 0.024 Uiso calc U . R 1 . .
C C28 0.73617(19) 0.31241(16) 1.18346(16) 0.0240(4) Uani d . . . 1 . .
H H28 0.8081 0.3553 1.1428 0.029 Uiso calc U . R 1 . .
C C29 0.70657(19) 0.29636(16) 1.30278(16) 0.0245(4) Uani d . . . 1 . .
H H29 0.759 0.3268 1.3444 0.029 Uiso calc U . R 1 . .
C C30 0.5994(2) 0.23523(17) 1.36139(15) 0.0253(4) Uani d . . . 1 . .
H H30 0.5779 0.2243 1.4433 0.03 Uiso calc U . R 1 . .
C C31 0.52394(19) 0.19024(16) 1.30045(14) 0.0214(4) Uani d . . . 1 . .
H H31 0.4502 0.1493 1.341 0.026 Uiso calc U . R 1 . .
N N1 0.41399(14) 0.17957(12) 0.73559(11) 0.0151(3) Uani d . . . 1 . .
N N2 0.51405(14) 0.16253(12) 0.99621(11) 0.0159(3) Uani d . . . 1 . .
O O1 0.71635(13) 0.34366(11) 0.57203(10) 0.0227(3) Uani d . . . 1 . .
O O2 0.29708(13) 0.31741(11) 0.93077(10) 0.0220(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.389(2) ?
C1 C6 . 1.396(2) ?
C2 C3 . 1.384(3) ?
C3 C4 . 1.382(3) ?
C4 C5 . 1.390(2) ?
C5 C6 . 1.395(2) ?
C6 C7 . 1.481(2) ?
C7 N1 . 1.283(2) ?
C7 C8 . 1.500(2) ?
C8 C9 . 1.531(2) ?
C9 C10 . 1.516(2) ?
C9 C17 . 1.584(2) ?
C10 O1 . 1.2196(19) ?
C10 C11 . 1.495(2) ?
C11 C16 . 1.389(2) ?
C11 C12 . 1.399(2) ?
C12 C13 . 1.385(2) ?
C13 C14 . 1.385(2) ?
C14 C15 . 1.393(2) ?
C15 C16 . 1.391(2) ?
C17 N1 . 1.4727(19) ?
C17 C20 . 1.518(2) ?
C17 C18 . 1.552(2) ?
C18 O2 . 1.2182(19) ?
C18 N2 . 1.366(2) ?
C19 C24 . 1.383(2) ?
C19 C20 . 1.397(2) ?
C19 N2 . 1.413(2) ?
C20 C21 . 1.382(2) ?
C21 C22 . 1.398(2) ?
C22 C23 . 1.387(2) ?
C23 C24 . 1.393(2) ?
C25 N2 . 1.4528(19) ?
C25 C26 . 1.514(2) ?
C26 C27 . 1.392(2) ?
C26 C31 . 1.392(2) ?
C27 C28 . 1.390(2) ?
C28 C29 . 1.383(2) ?
C29 C30 . 1.391(3) ?
C30 C31 . 1.385(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.15(16) ?
C3 C2 C1 . . 120.00(17) ?
C4 C3 C2 . . 120.40(16) ?
C3 C4 C5 . . 119.95(16) ?
C4 C5 C6 . . 120.20(16) ?
C5 C6 C1 . . 119.30(15) ?
C5 C6 C7 . . 120.26(15) ?
C1 C6 C7 . . 120.44(14) ?
N1 C7 C6 . . 121.80(14) ?
N1 C7 C8 . . 116.00(14) ?
C6 C7 C8 . . 122.20(14) ?
C7 C8 C9 . . 103.71(13) ?
C10 C9 C8 . . 114.05(13) ?
C10 C9 C17 . . 109.93(12) ?
C8 C9 C17 . . 103.61(12) ?
O1 C10 C11 . . 121.21(15) ?
O1 C10 C9 . . 120.94(14) ?
C11 C10 C9 . . 117.75(14) ?
C16 C11 C12 . . 119.75(15) ?
C16 C11 C10 . . 122.59(14) ?
C12 C11 C10 . . 117.65(14) ?
C13 C12 C11 . . 119.77(15) ?
C14 C13 C12 . . 120.32(16) ?
C13 C14 C15 . . 120.25(15) ?
C16 C15 C14 . . 119.51(16) ?
C11 C16 C15 . . 120.34(15) ?
N1 C17 C20 . . 110.89(12) ?
N1 C17 C18 . . 108.53(12) ?
C20 C17 C18 . . 101.78(12) ?
N1 C17 C9 . . 106.39(12) ?
C20 C17 C9 . . 120.03(12) ?
C18 C17 C9 . . 108.75(12) ?
O2 C18 N2 . . 126.37(15) ?
O2 C18 C17 . . 125.25(14) ?
N2 C18 C17 . . 108.37(13) ?
C24 C19 C20 . . 122.31(15) ?
C24 C19 N2 . . 127.75(15) ?
C20 C19 N2 . . 109.93(13) ?
C21 C20 C19 . . 119.83(14) ?
C21 C20 C17 . . 131.27(14) ?
C19 C20 C17 . . 108.72(13) ?
C20 C21 C22 . . 118.74(15) ?
C23 C22 C21 . . 120.43(16) ?
C22 C23 C24 . . 121.54(15) ?
C19 C24 C23 . . 117.13(15) ?
N2 C25 C26 . . 114.75(13) ?
C27 C26 C31 . . 118.55(15) ?
C27 C26 C25 . . 123.39(14) ?
C31 C26 C25 . . 118.04(14) ?
C28 C27 C26 . . 120.59(16) ?
C29 C28 C27 . . 120.36(16) ?
C28 C29 C30 . . 119.47(16) ?
C31 C30 C29 . . 120.04(16) ?
C30 C31 C26 . . 120.97(16) ?
C7 N1 C17 . . 110.15(13) ?
C18 N2 C19 . . 111.14(13) ?
C18 N2 C25 . . 123.59(13) ?
C19 N2 C25 . . 125.20(13) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436811'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         378.44

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.817(3)
_cell_length_b                   10.5300(12)
_cell_length_c                   9.5207(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.996(8)
_cell_angle_gamma                90
_cell_volume                     1872.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4362
_cell_measurement_theta_min      2.1809
_cell_measurement_theta_max      24.8197
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            31819
_diffrn_reflns_av_R_equivalents  0.2035
_diffrn_reflns_av_unetI/netI     0.1580
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_full        26.81
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             3967
_reflns_number_gt                1957
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1677
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2439
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      0.959
_refine_ls_number_reflns         3967
_refine_ls_number_parameters     356
_refine_ls_number_restraints     694
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1109P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(4)

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3994(2) 1.4197(3) 0.3438(4) 0.0268(10) Uani d . . . 1.0 . .
H H1 0.3684 1.4463 0.4098 0.032 Uiso calc U . R 1.0 . .
C C2 0.4570(2) 1.4944(4) 0.3202(4) 0.0281(10) Uani d . . . 1.0 . .
H H2 0.4656 1.5713 0.3717 0.034 Uiso calc U . R 1.0 . .
C C3 0.5020(2) 1.4597(4) 0.2237(5) 0.0303(10) Uani d . . . 1.0 . .
H H3 0.5414 1.5122 0.2082 0.036 Uiso calc U . R 1.0 . .
C C4 0.4892(2) 1.3467(4) 0.1488(5) 0.0305(10) Uani d . . . 1.0 . .
H H4 0.5199 1.322 0.0814 0.037 Uiso calc U . R 1.0 . .
C C5 0.43188(19) 1.2703(3) 0.1723(5) 0.0255(10) Uani d . . . 1.0 . .
H H5 0.4234 1.1934 0.1208 0.031 Uiso calc U . R 1.0 . .
C C6 0.38643(19) 1.3057(3) 0.2714(4) 0.0232(9) Uani d . . . 1.0 . .
C C7 0.32780(19) 1.2221(3) 0.3021(4) 0.0224(9) Uani d . . . 1.0 . .
C C8 0.2755(2) 1.2599(3) 0.4015(5) 0.0272(10) Uani d . . . 1.0 . .
H H8A 0.2515 1.341 0.3723 0.033 Uiso calc U . R 1.0 . .
H H8B 0.2993 1.2681 0.4997 0.033 Uiso calc U . R 1.0 . .
C C9 0.2223(2) 1.1492(3) 0.3878(4) 0.0257(9) Uani d . . . 1.0 . .
H H9 0.1784 1.1764 0.3254 0.031 Uiso calc U . R 1.0 . .
C C10 0.2015(2) 1.1072(4) 0.5219(5) 0.0296(10) Uani d . . . 1.0 . .
C C11 0.26170(18) 1.0435(3) 0.3079(4) 0.0227(9) Uani d . . . 1.0 . .
C C12 0.2089(2) 0.9835(4) 0.1926(4) 0.0265(10) Uani d . . . 1.0 . .
C C13 0.2519(2) 0.8233(3) 0.3406(4) 0.0264(9) Uani d . . . 1.0 . .
C C14 0.28870(18) 0.9294(3) 0.3950(4) 0.0210(9) Uani d . . . 1.0 . .
C C15 0.34104(19) 0.9188(3) 0.5081(4) 0.0244(9) Uani d . . . 1.0 . .
H H15 0.3668 0.9915 0.545 0.029 Uiso calc U . R 1.0 . .
C C16 0.3558(2) 0.7994(3) 0.5678(4) 0.0262(10) Uani d . . . 1.0 . .
H H16 0.3913 0.7903 0.6471 0.031 Uiso calc U . R 1.0 . .
C C17 0.3187(2) 0.6941(4) 0.5116(5) 0.0305(10) Uani d . . . 1.0 . .
H H17 0.3296 0.6132 0.5529 0.037 Uiso calc U . R 1.0 . .
C C18 0.2660(2) 0.7030(4) 0.3965(5) 0.0343(11) Uani d . . . 1.0 . .
H H18 0.2409 0.6303 0.3579 0.041 Uiso calc U . R 1.0 . .
C C19 0.1433(6) 0.7727(12) 0.1668(13) 0.025(2) Uani d U P D 0.487(3) A 1
H H19A 0.1642 0.6897 0.1452 0.03 Uiso calc U P R 0.487(3) A 1
H H19B 0.1209 0.8087 0.076 0.03 Uiso calc U P R 0.487(3) A 1
C C20 0.0847(3) 0.7481(6) 0.2580(6) 0.0223(18) Uani d U P DG 0.487(3) A 1
C C21 0.0545(3) 0.8498(4) 0.3225(7) 0.0251(19) Uani d U P DG 0.487(3) A 1
H H21 0.072 0.9334 0.3116 0.03 Uiso calc U P R 0.487(3) A 1
C C22 -0.0014(3) 0.8292(5) 0.4028(7) 0.0300(19) Uani d U P DG 0.487(3) A 1
H H22 -0.022 0.8987 0.4468 0.036 Uiso calc U P R 0.487(3) A 1
C C23 -0.0270(3) 0.7069(5) 0.4187(6) 0.0322(18) Uani d U P DG 0.487(3) A 1
H H23 -0.0652 0.6928 0.4736 0.039 Uiso calc U P R 0.487(3) A 1
C C24 0.0032(3) 0.6052(4) 0.3542(7) 0.033(2) Uani d U P DG 0.487(3) A 1
H H24 -0.0143 0.5216 0.3651 0.04 Uiso calc U P R 0.487(3) A 1
C C25 0.0591(3) 0.6258(5) 0.2739(7) 0.0263(19) Uani d U P DG 0.487(3) A 1
H H25 0.0797 0.5563 0.2299 0.032 Uiso calc U P R 0.487(3) A 1
C C19A 0.1566(12) 0.775(4) 0.130(3) 0.023(3) Uani d U P D 0.262(3) A 2
H H19C 0.18 0.6914 0.1204 0.027 Uiso calc U P R 0.262(3) A 2
H H19D 0.1455 0.813 0.0355 0.027 Uiso calc U P R 0.262(3) A 2
C C20A 0.0897(5) 0.7584(11) 0.1989(12) 0.021(2) Uani d U P DG 0.262(3) A 2
C C21A 0.0356(5) 0.8486(9) 0.1753(11) 0.028(3) Uani d U P DG 0.262(3) A 2
H H21A 0.0422 0.9215 0.1194 0.033 Uiso calc U P R 0.262(3) A 2
C C22A -0.0280(5) 0.8323(9) 0.2333(12) 0.032(3) Uani d U P DG 0.262(3) A 2
H H22A -0.065 0.894 0.2172 0.038 Uiso calc U P R 0.262(3) A 2
C C23A -0.0377(5) 0.7257(11) 0.3150(13) 0.034(3) Uani d U P DG 0.262(3) A 2
H H23A -0.0812 0.7146 0.3546 0.041 Uiso calc U P R 0.262(3) A 2
C C24A 0.0163(6) 0.6354(10) 0.3386(14) 0.032(3) Uani d U P DG 0.262(3) A 2
H H24A 0.0097 0.5626 0.3944 0.039 Uiso calc U P R 0.262(3) A 2
C C25A 0.0800(5) 0.6518(10) 0.2805(14) 0.026(3) Uani d U P DG 0.262(3) A 2
H H25A 0.1169 0.5901 0.2967 0.032 Uiso calc U P R 0.262(3) A 2
C C19B 0.1584(15) 0.770(4) 0.134(4) 0.022(4) Uani d U P D 0.251(3) A 3
H H19E 0.1838 0.6876 0.1286 0.027 Uiso calc U P R 0.251(3) A 3
H H19F 0.1484 0.8042 0.0366 0.027 Uiso calc U P R 0.251(3) A 3
C C20B 0.0896(5) 0.7493(11) 0.1945(12) 0.022(3) Uani d U P DG 0.251(3) A 3
C C21B 0.0746(6) 0.8208(11) 0.3100(13) 0.021(3) Uani d U P DG 0.251(3) A 3
H H21B 0.1084 0.8811 0.3514 0.025 Uiso calc U P R 0.251(3) A 3
C C22B 0.0101(6) 0.8040(11) 0.3649(12) 0.027(3) Uani d U P DG 0.251(3) A 3
H H22B -0.0002 0.8529 0.4439 0.033 Uiso calc U P R 0.251(3) A 3
C C23B -0.0393(5) 0.7157(11) 0.3044(13) 0.032(3) Uani d U P DG 0.251(3) A 3
H H23B -0.0834 0.7042 0.3419 0.038 Uiso calc U P R 0.251(3) A 3
C C24B -0.0243(5) 0.6442(9) 0.1889(12) 0.027(3) Uani d U P DG 0.251(3) A 3
H H24B -0.0581 0.5838 0.1475 0.032 Uiso calc U P R 0.251(3) A 3
C C25B 0.0402(5) 0.6610(10) 0.1339(10) 0.024(3) Uani d U P DG 0.251(3) A 3
H H25B 0.0505 0.6121 0.055 0.029 Uiso calc U P R 0.251(3) A 3
N N1 0.32004(15) 1.1103(3) 0.2494(3) 0.0231(8) Uani d . . . 1.0 . .
N N2 0.20304(16) 0.8576(3) 0.2224(4) 0.0278(8) Uani d U . D 1.0 . .
N N3 0.18719(19) 1.0737(3) 0.6290(5) 0.0414(10) Uani d . . . 1.0 . .
O O1 0.17631(14) 1.0400(2) 0.0917(3) 0.0321(7) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.379(5) ?
C1 C6 . 1.391(5) ?
C2 C3 . 1.373(6) ?
C3 C4 . 1.393(6) ?
C4 C5 . 1.386(5) ?
C5 C6 . 1.399(5) ?
C6 C7 . 1.469(5) ?
C7 N1 . 1.281(4) ?
C7 C8 . 1.501(5) ?
C8 C9 . 1.531(5) ?
C9 C10 . 1.450(6) ?
C9 C11 . 1.582(5) ?
C10 N3 . 1.142(5) ?
C11 N1 . 1.469(5) ?
C11 C14 . 1.512(5) ?
C11 C12 . 1.525(5) ?
C12 O1 . 1.229(4) ?
C12 N2 . 1.363(5) ?
C13 C14 . 1.382(5) ?
C13 C18 . 1.387(5) ?
C13 N2 . 1.411(5) ?
C14 C15 . 1.372(5) ?
C15 C16 . 1.394(5) ?
C16 C17 . 1.382(5) ?
C17 C18 . 1.388(6) ?
C19 N2 . 1.482(9) ?
C19 C20 . 1.508(9) ?
C20 C21 . 1.39 ?
C20 C25 . 1.39 ?
C21 C22 . 1.39 ?
C22 C23 . 1.39 ?
C23 C24 . 1.39 ?
C24 C25 . 1.39 ?
C19A N2 . 1.451(14) ?
C19A C20A . 1.497(13) ?
C20A C21A . 1.39 ?
C20A C25A . 1.39 ?
C21A C22A . 1.39 ?
C22A C23A . 1.39 ?
C23A C24A . 1.39 ?
C24A C25A . 1.39 ?
C19B N2 . 1.451(13) ?
C19B C20B . 1.496(13) ?
C20B C21B . 1.39 ?
C20B C25B . 1.39 ?
C21B C22B . 1.39 ?
C22B C23B . 1.39 ?
C23B C24B . 1.39 ?
C24B C25B . 1.39 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.4(4) ?
C3 C2 C1 . . 121.2(4) ?
C2 C3 C4 . . 119.2(4) ?
C5 C4 C3 . . 120.2(4) ?
C4 C5 C6 . . 120.4(4) ?
C1 C6 C5 . . 118.6(4) ?
C1 C6 C7 . . 120.6(4) ?
C5 C6 C7 . . 120.7(3) ?
N1 C7 C6 . . 121.7(4) ?
N1 C7 C8 . . 116.0(3) ?
C6 C7 C8 . . 122.2(3) ?
C7 C8 C9 . . 102.5(3) ?
C10 C9 C8 . . 113.6(3) ?
C10 C9 C11 . . 113.7(3) ?
C8 C9 C11 . . 103.7(3) ?
N3 C10 C9 . . 178.0(5) ?
N1 C11 C14 . . 111.8(3) ?
N1 C11 C12 . . 112.1(3) ?
C14 C11 C12 . . 102.2(3) ?
N1 C11 C9 . . 105.1(3) ?
C14 C11 C9 . . 116.1(3) ?
C12 C11 C9 . . 109.6(3) ?
O1 C12 N2 . . 126.0(4) ?
O1 C12 C11 . . 125.6(3) ?
N2 C12 C11 . . 108.4(3) ?
C14 C13 C18 . . 122.0(4) ?
C14 C13 N2 . . 109.9(3) ?
C18 C13 N2 . . 128.0(3) ?
C15 C14 C13 . . 120.5(3) ?
C15 C14 C11 . . 131.0(3) ?
C13 C14 C11 . . 108.5(3) ?
C14 C15 C16 . . 118.8(3) ?
C17 C16 C15 . . 119.9(4) ?
C16 C17 C18 . . 122.0(4) ?
C13 C18 C17 . . 116.7(4) ?
N2 C19 C20 . . 118.3(7) ?
C21 C20 C25 . . 120.0 ?
C21 C20 C19 . . 119.3(6) ?
C25 C20 C19 . . 120.7(5) ?
C20 C21 C22 . . 120.0 ?
C23 C22 C21 . . 120.0 ?
C22 C23 C24 . . 120.0 ?
C25 C24 C23 . . 120.0 ?
C24 C25 C20 . . 120.0 ?
N2 C19A C20A . . 106.4(11) ?
C21A C20A C25A . . 120.0 ?
C21A C20A C19A . . 119.3(18) ?
C25A C20A C19A . . 120.6(18) ?
C22A C21A C20A . . 120.0 ?
C21A C22A C23A . . 120.0 ?
C22A C23A C24A . . 120.0 ?
C25A C24A C23A . . 120.0 ?
C24A C25A C20A . . 120.0 ?
N2 C19B C20B . . 109.4(11) ?
C21B C20B C25B . . 120.0 ?
C21B C20B C19B . . 119.8(8) ?
C25B C20B C19B . . 120.1(8) ?
C20B C21B C22B . . 120.0 ?
C23B C22B C21B . . 120.0 ?
C22B C23B C24B . . 120.0 ?
C25B C24B C23B . . 120.0 ?
C24B C25B C20B . . 120.0 ?
C7 N1 C11 . . 110.3(3) ?
C12 N2 C13 . . 110.7(3) ?
C12 N2 C19B . . 124.(2) ?
C13 N2 C19B . . 125.(2) ?
C12 N2 C19A . . 121.(2) ?
C13 N2 C19A . . 128.(2) ?
C12 N2 C19 . . 126.1(7) ?
C13 N2 C19 . . 121.5(7) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436812'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         461.96

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4690(9)
_cell_length_b                   10.0316(11)
_cell_length_c                   13.1967(13)
_cell_angle_alpha                83.975(3)
_cell_angle_beta                 70.468(3)
_cell_angle_gamma                85.668(3)
_cell_volume                     1173.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4409
_cell_measurement_theta_min      2.2843
_cell_measurement_theta_max      29.0422
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            28776
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         31.03
_diffrn_reflns_theta_full        31.03
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             7442
_reflns_number_gt                5182
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1631
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         7442
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.1773P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.472
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.04130(17) 0.53342(16) 0.78120(13) 0.0121(3) Uani d . . . 1 . .
C C2 0.10609(17) 0.38688(15) 0.78247(13) 0.0109(3) Uani d . . . 1 . .
C C3 0.20511(17) 0.35382(15) 0.66615(12) 0.0109(3) Uani d . . . 1 . .
H H3 0.1709 0.4142 0.6128 0.013 Uiso calc U . R 1 . .
C C4 0.16569(17) 0.20954(15) 0.66089(13) 0.0120(3) Uani d . . . 1 . .
H H4 0.239 0.1481 0.6846 0.014 Uiso calc U . R 1 . .
C C5 0.17183(18) 0.17130(17) 0.55026(14) 0.0150(3) Uani d . . . 1 . .
H H5A 0.2782 0.167 0.5036 0.018 Uiso calc U . R 1 . .
H H5B 0.134 0.0799 0.5595 0.018 Uiso calc U . R 1 . .
C C6 0.08408(19) 0.26405(18) 0.49092(14) 0.0176(3) Uani d . . . 1 . .
H H6A 0.0922 0.2251 0.4232 0.021 Uiso calc U . R 1 . .
H H6B 0.1326 0.3514 0.4707 0.021 Uiso calc U . R 1 . .
C C7 -0.08287(19) 0.29011(18) 0.55335(15) 0.0187(4) Uani d . . . 1 . .
H H7A -0.1291 0.3453 0.505 0.022 Uiso calc U . R 1 . .
H H7B -0.0912 0.3432 0.6144 0.022 Uiso calc U . R 1 . .
C C8 -0.1737(2) 0.16262(19) 0.59818(15) 0.0215(4) Uani d . . . 1 . .
H H8A -0.2663 0.1734 0.5785 0.026 Uiso calc U . R 1 . .
H H8B -0.1138 0.0854 0.562 0.026 Uiso calc U . R 1 . .
C C9 -0.21779(19) 0.12911(19) 0.72007(16) 0.0222(4) Uani d . . . 1 . .
H H9A -0.2877 0.0548 0.7405 0.027 Uiso calc U . R 1 . .
H H9B -0.2734 0.2082 0.756 0.027 Uiso calc U . R 1 . .
C C10 -0.08812(19) 0.08871(17) 0.76484(15) 0.0176(3) Uani d . . . 1 . .
H H10A -0.1307 0.0594 0.8426 0.021 Uiso calc U . R 1 . .
H H10B -0.0298 0.0114 0.7277 0.021 Uiso calc U . R 1 . .
C C11 0.01571(17) 0.20028(16) 0.75080(13) 0.0130(3) Uani d . . . 1 . .
C C12 0.18670(17) 0.38532(15) 0.86390(13) 0.0117(3) Uani d . . . 1 . .
C C13 0.26482(18) 0.28182(17) 0.90198(13) 0.0158(3) Uani d . . . 1 . .
H H13 0.2747 0.1949 0.8773 0.019 Uiso calc U . R 1 . .
C C14 0.3286(2) 0.30976(18) 0.97802(14) 0.0198(4) Uani d . . . 1 . .
C C15 0.31433(19) 0.43548(19) 1.01525(14) 0.0198(4) Uani d . . . 1 . .
H H15 0.3588 0.4507 1.0676 0.024 Uiso calc U . R 1 . .
C C16 0.23539(18) 0.54022(18) 0.97683(13) 0.0164(3) Uani d . . . 1 . .
H H16 0.2252 0.627 1.0018 0.02 Uiso calc U . R 1 . .
C C17 0.17236(17) 0.51308(15) 0.90083(13) 0.0118(3) Uani d . . . 1 . .
C C18 0.05937(18) 0.74280(16) 0.86223(14) 0.0158(3) Uani d . . . 1 . .
H H18A 0.0322 0.7597 0.9391 0.019 Uiso calc U . R 1 . .
H H18B -0.0255 0.7762 0.8372 0.019 Uiso calc U . R 1 . .
C C19 0.19777(18) 0.81816(15) 0.79693(14) 0.0138(3) Uani d . . . 1 . .
C C20 0.25521(18) 0.81348(16) 0.68486(14) 0.0152(3) Uani d . . . 1 . .
H H20 0.2041 0.7667 0.6496 0.018 Uiso calc U . R 1 . .
C C21 0.38638(19) 0.87680(16) 0.62482(14) 0.0163(3) Uani d . . . 1 . .
H H21 0.4249 0.8728 0.5488 0.02 Uiso calc U . R 1 . .
C C22 0.46150(18) 0.94620(16) 0.67592(14) 0.0163(3) Uani d . . . 1 . .
H H22 0.5515 0.9891 0.635 0.02 Uiso calc U . R 1 . .
C C23 0.40435(19) 0.95244(16) 0.78667(15) 0.0166(3) Uani d . . . 1 . .
H H23 0.455 1.0004 0.8215 0.02 Uiso calc U . R 1 . .
C C24 0.27317(19) 0.88884(16) 0.84721(14) 0.0157(3) Uani d . . . 1 . .
H H24 0.2348 0.8936 0.9231 0.019 Uiso calc U . R 1 . .
C C25 0.37032(17) 0.37206(16) 0.64306(13) 0.0119(3) Uani d . . . 1 . .
C C26 0.55016(18) 0.53548(17) 0.62528(14) 0.0156(3) Uani d . . . 1 . .
H H26A 0.5709 0.6249 0.5852 0.019 Uiso calc U . R 1 . .
H H26B 0.6208 0.4687 0.5819 0.019 Uiso calc U . R 1 . .
C C27 0.5744(2) 0.5360(2) 0.73227(15) 0.0255(4) Uani d . . . 1 . .
H H27A 0.5087 0.6059 0.7734 0.038 Uiso calc U . R 1 . .
H H27B 0.6793 0.5541 0.7202 0.038 Uiso calc U . R 1 . .
H H27C 0.5509 0.4484 0.7729 0.038 Uiso calc U . R 1 . .
Cl Cl1 0.42768(7) 0.18062(6) 1.02823(5) 0.03899(16) Uani d . . . 1 . .
N N1 0.08486(15) 0.59844(13) 0.85156(11) 0.0122(3) Uani d . . . 1 . .
N N2 -0.01571(15) 0.29111(14) 0.81740(11) 0.0135(3) Uani d . . . 1 . .
O O1 -0.03137(13) 0.58251(12) 0.72544(10) 0.0182(3) Uani d . . . 1 . .
O O2 0.46598(13) 0.28262(12) 0.62878(11) 0.0206(3) Uani d . . . 1 . .
O O3 0.39606(12) 0.50263(11) 0.64047(9) 0.0139(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.212(2) ?
C1 N1 . 1.372(2) ?
C1 C2 . 1.550(2) ?
C2 N2 . 1.4780(19) ?
C2 C12 . 1.510(2) ?
C2 C3 . 1.563(2) ?
C3 C25 . 1.512(2) ?
C3 C4 . 1.536(2) ?
C4 C11 . 1.518(2) ?
C4 C5 . 1.529(2) ?
C5 C6 . 1.528(2) ?
C6 C7 . 1.536(2) ?
C7 C8 . 1.547(2) ?
C8 C9 . 1.527(3) ?
C9 C10 . 1.543(3) ?
C10 C11 . 1.502(2) ?
C11 N2 . 1.282(2) ?
C12 C13 . 1.379(2) ?
C12 C17 . 1.400(2) ?
C13 C14 . 1.393(2) ?
C14 C15 . 1.382(3) ?
C14 Cl1 . 1.7461(18) ?
C15 C16 . 1.394(3) ?
C16 C17 . 1.385(2) ?
C17 N1 . 1.407(2) ?
C18 N1 . 1.464(2) ?
C18 C19 . 1.513(2) ?
C19 C24 . 1.395(2) ?
C19 C20 . 1.399(2) ?
C20 C21 . 1.389(2) ?
C21 C22 . 1.393(2) ?
C22 C23 . 1.385(2) ?
C23 C24 . 1.392(2) ?
C25 O2 . 1.2081(19) ?
C25 O3 . 1.3452(19) ?
C26 O3 . 1.4632(19) ?
C26 C27 . 1.505(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 126.20(15) ?
O1 C1 C2 . . 125.82(14) ?
N1 C1 C2 . . 107.95(13) ?
N2 C2 C12 . . 111.82(13) ?
N2 C2 C1 . . 110.74(12) ?
C12 C2 C1 . . 101.89(12) ?
N2 C2 C3 . . 105.94(12) ?
C12 C2 C3 . . 116.11(12) ?
C1 C2 C3 . . 110.39(13) ?
C25 C3 C4 . . 114.34(13) ?
C25 C3 C2 . . 113.18(13) ?
C4 C3 C2 . . 103.21(12) ?
C11 C4 C5 . . 117.06(13) ?
C11 C4 C3 . . 101.02(12) ?
C5 C4 C3 . . 116.40(13) ?
C6 C5 C4 . . 116.57(13) ?
C5 C6 C7 . . 115.98(14) ?
C6 C7 C8 . . 115.01(14) ?
C9 C8 C7 . . 115.62(15) ?
C8 C9 C10 . . 116.28(15) ?
C11 C10 C9 . . 113.22(14) ?
N2 C11 C10 . . 121.29(15) ?
N2 C11 C4 . . 116.06(14) ?
C10 C11 C4 . . 122.60(14) ?
C13 C12 C17 . . 120.93(15) ?
C13 C12 C2 . . 129.92(14) ?
C17 C12 C2 . . 109.15(13) ?
C12 C13 C14 . . 117.39(15) ?
C15 C14 C13 . . 122.02(16) ?
C15 C14 Cl1 . . 119.47(14) ?
C13 C14 Cl1 . . 118.51(14) ?
C14 C15 C16 . . 120.66(16) ?
C17 C16 C15 . . 117.54(16) ?
C16 C17 C12 . . 121.47(15) ?
C16 C17 N1 . . 129.07(15) ?
C12 C17 N1 . . 109.43(14) ?
N1 C18 C19 . . 111.13(13) ?
C24 C19 C20 . . 118.98(15) ?
C24 C19 C18 . . 120.93(15) ?
C20 C19 C18 . . 120.06(14) ?
C21 C20 C19 . . 120.49(15) ?
C20 C21 C22 . . 120.08(16) ?
C23 C22 C21 . . 119.71(15) ?
C22 C23 C24 . . 120.42(16) ?
C23 C24 C19 . . 120.32(16) ?
O2 C25 O3 . . 124.62(14) ?
O2 C25 C3 . . 125.12(14) ?
O3 C25 C3 . . 110.26(13) ?
O3 C26 C27 . . 110.79(13) ?
C1 N1 C17 . . 111.56(13) ?
C1 N1 C18 . . 123.37(14) ?
C17 N1 C18 . . 124.61(14) ?
C11 N2 C2 . . 108.91(13) ?
C25 O3 C26 . . 116.65(12) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436813'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         321.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3566(6)
_cell_length_b                   17.7311(14)
_cell_length_c                   10.5304(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.637(5)
_cell_angle_gamma                90
_cell_volume                     1528.24(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1518
_cell_measurement_theta_min      2.7409
_cell_measurement_theta_max      26.2327
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.380
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            20715
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_unetI/netI     0.1724
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         38.64
_diffrn_reflns_theta_full        38.64
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             8575
_reflns_number_gt                4574
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2231
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_number_reflns         8575
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.16826(18) 0.29991(9) 0.57382(14) 0.0127(3) Uani d . . . 1 . .
C C2 0.1890(2) 0.23219(10) 0.51201(15) 0.0162(3) Uani d . . . 1 . .
H H2 0.2603 0.2304 0.4523 0.019 Uiso calc U . R 1 . .
C C3 0.1075(2) 0.16732(10) 0.53612(16) 0.0195(3) Uani d . . . 1 . .
H H3 0.124 0.1215 0.4938 0.023 Uiso calc U . R 1 . .
C C4 0.0014(2) 0.16936(10) 0.62250(16) 0.0189(3) Uani d . . . 1 . .
H H4 -0.056 0.1252 0.638 0.023 Uiso calc U . R 1 . .
C C5 -0.0203(2) 0.23593(10) 0.68567(15) 0.0162(3) Uani d . . . 1 . .
H H5 -0.0912 0.2376 0.7457 0.019 Uiso calc U . R 1 . .
C C6 0.06257(18) 0.29995(9) 0.66018(14) 0.0133(3) Uani d . . . 1 . .
C C7 0.12173(18) 0.42865(9) 0.72902(14) 0.0123(3) Uani d . . . 1 . .
C C8 0.26524(17) 0.42946(9) 0.65935(13) 0.0105(2) Uani d . . . 1 . .
C C9 0.24971(18) 0.37154(9) 0.54779(14) 0.0125(3) Uani d . . . 1 . .
H H9 0.3615 0.3595 0.5332 0.015 Uiso calc U . R 1 . .
C C10 0.1577(2) 0.41799(10) 0.43111(14) 0.0166(3) Uani d . . . 1 . .
H H10A 0.1929 0.4029 0.3505 0.02 Uiso calc U . R 1 . .
H H10B 0.0383 0.4101 0.4193 0.02 Uiso calc U . R 1 . .
C C11 0.26119(18) 0.50384(9) 0.58274(14) 0.0121(3) Uani d . . . 1 . .
C C12 0.31864(17) 0.57755(9) 0.63886(14) 0.0121(3) Uani d . . . 1 . .
C C13 0.38068(19) 0.58776(10) 0.77158(14) 0.0142(3) Uani d . . . 1 . .
H H13 0.3809 0.5467 0.8296 0.017 Uiso calc U . R 1 . .
C C14 0.4417(2) 0.65699(10) 0.81889(16) 0.0178(3) Uani d . . . 1 . .
H H14 0.4853 0.663 0.9089 0.021 Uiso calc U . R 1 . .
C C15 0.4394(2) 0.71772(11) 0.73552(17) 0.0206(3) Uani d . . . 1 . .
H H15 0.4817 0.7652 0.7683 0.025 Uiso calc U . R 1 . .
C C16 0.3751(2) 0.70902(10) 0.60415(16) 0.0188(3) Uani d . . . 1 . .
H H16 0.3714 0.7508 0.5472 0.023 Uiso calc U . R 1 . .
C C17 0.3163(2) 0.63957(10) 0.55595(15) 0.0156(3) Uani d . . . 1 . .
H H17 0.274 0.6339 0.4657 0.019 Uiso calc U . R 1 . .
C C18 0.41803(18) 0.41563(9) 0.76337(14) 0.0119(3) Uani d . . . 1 . .
C C19 0.70288(19) 0.43057(12) 0.81798(17) 0.0211(4) Uani d . . . 1 . .
H H19A 0.6943 0.4618 0.8931 0.032 Uiso calc U . R 1 . .
H H19B 0.7936 0.4487 0.78 0.032 Uiso calc U . R 1 . .
H H19C 0.7228 0.378 0.8455 0.032 Uiso calc U . R 1 . .
N N1 0.19902(17) 0.49682(8) 0.46188(12) 0.0159(3) Uani d . . . 1 . .
O O1 0.03059(13) 0.36554(7) 0.72428(11) 0.0149(2) Uani d . . . 1 . .
O O2 0.08732(14) 0.48160(7) 0.78919(11) 0.0154(2) Uani d . . . 1 . .
O O3 0.41521(14) 0.38919(8) 0.86878(11) 0.0184(3) Uani d . . . 1 . .
O O4 0.55190(13) 0.43536(7) 0.72221(10) 0.0155(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.390(2) ?
C1 C2 . 1.393(2) ?
C1 C9 . 1.492(2) ?
C2 C3 . 1.386(2) ?
C3 C4 . 1.393(2) ?
C4 C5 . 1.385(2) ?
C5 C6 . 1.384(2) ?
C6 O1 . 1.397(2) ?
C7 O2 . 1.1995(19) ?
C7 O1 . 1.3489(19) ?
C7 C8 . 1.527(2) ?
C8 C18 . 1.525(2) ?
C8 C11 . 1.543(2) ?
C8 C9 . 1.546(2) ?
C9 C10 . 1.549(2) ?
C10 N1 . 1.461(2) ?
C11 N1 . 1.2800(19) ?
C11 C12 . 1.474(2) ?
C12 C13 . 1.401(2) ?
C12 C17 . 1.402(2) ?
C13 C14 . 1.383(2) ?
C14 C15 . 1.387(3) ?
C15 C16 . 1.388(2) ?
C16 C17 . 1.384(2) ?
C18 O3 . 1.2095(18) ?
C18 O4 . 1.3257(18) ?
C19 O4 . 1.450(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 117.49(15) ?
C6 C1 C9 . . 119.56(14) ?
C2 C1 C9 . . 122.92(14) ?
C3 C2 C1 . . 121.18(15) ?
C2 C3 C4 . . 119.94(16) ?
C5 C4 C3 . . 119.89(16) ?
C6 C5 C4 . . 119.13(15) ?
C5 C6 C1 . . 122.38(15) ?
C5 C6 O1 . . 115.92(13) ?
C1 C6 O1 . . 121.69(14) ?
O2 C7 O1 . . 118.37(13) ?
O2 C7 C8 . . 122.79(15) ?
O1 C7 C8 . . 118.84(13) ?
C18 C8 C7 . . 106.16(11) ?
C18 C8 C11 . . 116.10(13) ?
C7 C8 C11 . . 108.84(12) ?
C18 C8 C9 . . 111.63(12) ?
C7 C8 C9 . . 113.90(12) ?
C11 C8 C9 . . 100.42(11) ?
C1 C9 C8 . . 113.41(12) ?
C1 C9 C10 . . 115.24(13) ?
C8 C9 C10 . . 101.64(12) ?
N1 C10 C9 . . 106.00(12) ?
N1 C11 C12 . . 121.25(14) ?
N1 C11 C8 . . 113.49(14) ?
C12 C11 C8 . . 125.25(12) ?
C13 C12 C17 . . 118.41(15) ?
C13 C12 C11 . . 122.65(14) ?
C17 C12 C11 . . 118.91(13) ?
C14 C13 C12 . . 120.63(15) ?
C13 C14 C15 . . 120.27(15) ?
C14 C15 C16 . . 119.85(17) ?
C17 C16 C15 . . 120.13(16) ?
C16 C17 C12 . . 120.69(15) ?
O3 C18 O4 . . 125.19(14) ?
O3 C18 C8 . . 123.57(13) ?
O4 C18 C8 . . 111.23(12) ?
C11 N1 C10 . . 110.12(13) ?
C7 O1 C6 . . 123.15(12) ?
C18 O4 C19 . . 115.49(12) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436814'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         426.50

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2128(6)
_cell_length_b                   12.0722(9)
_cell_length_c                   12.1473(10)
_cell_angle_alpha                80.826(3)
_cell_angle_beta                 73.356(3)
_cell_angle_gamma                74.316(2)
_cell_volume                     1106.54(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6856
_cell_measurement_theta_min      2.3732
_cell_measurement_theta_max      30.6607
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            46069
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         31.07
_diffrn_reflns_theta_full        31.07
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             7077
_reflns_number_gt                5034
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1554
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         7077
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.4331P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.39480(18) 0.22002(12) 0.37092(12) 0.0127(3) Uani d . . . 1 . .
C C2 0.38139(18) 0.13165(11) 0.29664(12) 0.0122(3) Uani d . . . 1 . .
C C3 0.36719(18) 0.20466(12) 0.18511(12) 0.0126(3) Uani d . . . 1 . .
C C4 0.3496(2) 0.17689(13) 0.08405(13) 0.0163(3) Uani d . . . 1 . .
H H4 0.3452 0.1007 0.0764 0.02 Uiso calc U . R 1 . .
C C5 0.3384(2) 0.26298(14) -0.00688(14) 0.0201(3) Uani d . . . 1 . .
H H5 0.3265 0.2452 -0.0772 0.024 Uiso calc U . R 1 . .
C C6 0.3445(2) 0.37463(14) 0.00439(14) 0.0208(3) Uani d . . . 1 . .
H H6 0.3367 0.432 -0.0585 0.025 Uiso calc U . R 1 . .
C C7 0.3620(2) 0.40387(13) 0.10668(14) 0.0177(3) Uani d . . . 1 . .
H H7 0.3668 0.4799 0.1146 0.021 Uiso calc U . R 1 . .
C C8 0.37193(18) 0.31744(12) 0.19573(12) 0.0128(3) Uani d . . . 1 . .
C C9 0.54458(19) 0.02651(12) 0.29029(13) 0.0135(3) Uani d . . . 1 . .
H H9 0.5907 0.0248 0.3585 0.016 Uiso calc U . R 1 . .
C C10 0.46962(19) -0.07820(12) 0.30688(13) 0.0150(3) Uani d . . . 1 . .
H H10A 0.5461 -0.1479 0.3365 0.018 Uiso calc U . R 1 . .
H H10B 0.4509 -0.0933 0.2342 0.018 Uiso calc U . R 1 . .
C C11 0.29615(19) -0.04068(12) 0.39640(13) 0.0135(3) Uani d . . . 1 . .
H H11 0.3187 -0.0383 0.4725 0.016 Uiso calc U . R 1 . .
C C12 0.3930(2) 0.42884(13) 0.35047(14) 0.0174(3) Uani d . . . 1 . .
H H12A 0.3661 0.4174 0.4357 0.021 Uiso calc U . R 1 . .
H H12B 0.3007 0.4939 0.3296 0.021 Uiso calc U . R 1 . .
C C13 0.56713(19) 0.46173(12) 0.30525(13) 0.0141(3) Uani d . . . 1 . .
C C14 0.5769(2) 0.57157(13) 0.32211(14) 0.0199(3) Uani d . . . 1 . .
H H14 0.4747 0.6245 0.3594 0.024 Uiso calc U . R 1 . .
C C15 0.7353(2) 0.60341(13) 0.28459(15) 0.0213(3) Uani d . . . 1 . .
H H15 0.7411 0.6778 0.2971 0.026 Uiso calc U . R 1 . .
C C16 0.8854(2) 0.52758(13) 0.22898(15) 0.0201(3) Uani d . . . 1 . .
H H16 0.9933 0.5501 0.2028 0.024 Uiso calc U . R 1 . .
C C17 0.8767(2) 0.41864(13) 0.21178(14) 0.0199(3) Uani d . . . 1 . .
H H17 0.979 0.3663 0.1737 0.024 Uiso calc U . R 1 . .
C C18 0.7183(2) 0.38601(12) 0.25022(13) 0.0164(3) Uani d . . . 1 . .
H H18 0.7135 0.3111 0.2387 0.02 Uiso calc U . R 1 . .
C C19 0.69162(19) 0.03299(12) 0.18365(13) 0.0151(3) Uani d . . . 1 . .
C C20 0.9115(2) 0.13673(14) 0.08965(15) 0.0232(3) Uani d . . . 1 . .
H H20A 0.9843 0.0608 0.0643 0.028 Uiso calc U . R 1 . .
H H20B 0.9852 0.1753 0.1148 0.028 Uiso calc U . R 1 . .
C C21 0.8496(3) 0.20878(17) -0.00943(17) 0.0356(5) Uani d . . . 1 . .
H H21A 0.7873 0.1669 -0.0398 0.053 Uiso calc U . R 1 . .
H H21B 0.9504 0.2249 -0.0703 0.053 Uiso calc U . R 1 . .
H H21C 0.7706 0.2817 0.0169 0.053 Uiso calc U . R 1 . .
C C22 0.17742(19) -0.12015(12) 0.40925(13) 0.0141(3) Uani d . . . 1 . .
C C23 0.0679(2) -0.10735(14) 0.33747(14) 0.0209(3) Uani d . . . 1 . .
H H23 0.0558 -0.0415 0.2833 0.025 Uiso calc U . R 1 . .
C C24 -0.0242(2) -0.19049(15) 0.34438(15) 0.0240(3) Uani d . . . 1 . .
H H24 -0.099 -0.181 0.2949 0.029 Uiso calc U . R 1 . .
C C25 -0.0078(2) -0.28727(13) 0.42312(14) 0.0201(3) Uani d . . . 1 . .
H H25 -0.0691 -0.3446 0.4264 0.024 Uiso calc U . R 1 . .
C C26 0.0984(2) -0.29975(13) 0.49669(14) 0.0190(3) Uani d . . . 1 . .
H H26 0.1088 -0.3652 0.5515 0.023 Uiso calc U . R 1 . .
C C27 0.1898(2) -0.21623(13) 0.49025(13) 0.0171(3) Uani d . . . 1 . .
H H27 0.2615 -0.2246 0.5415 0.021 Uiso calc U . R 1 . .
N N1 0.38644(16) 0.32499(10) 0.30709(11) 0.0138(2) Uani d . . . 1 . .
N N2 0.23221(16) 0.07772(10) 0.34766(11) 0.0142(2) Uani d . . . 1 . .
H H1N 0.146(3) 0.1245(16) 0.4014(17) 0.021 Uiso d U . . 1 . .
O O1 0.41129(14) 0.20043(9) 0.46909(9) 0.0179(2) Uani d . . . 1 . .
O O2 0.74103(15) -0.03108(10) 0.10784(10) 0.0241(3) Uani d . . . 1 . .
O O3 0.76498(14) 0.11928(9) 0.18640(9) 0.0172(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2172(18) ?
C1 N1 . 1.3718(18) ?
C1 C2 . 1.5465(19) ?
C2 N2 . 1.4754(18) ?
C2 C3 . 1.510(2) ?
C2 C9 . 1.570(2) ?
C3 C4 . 1.378(2) ?
C3 C8 . 1.3997(19) ?
C4 C5 . 1.396(2) ?
C5 C6 . 1.392(2) ?
C6 C7 . 1.399(2) ?
C7 C8 . 1.382(2) ?
C8 N1 . 1.4106(18) ?
C9 C19 . 1.505(2) ?
C9 C10 . 1.5120(19) ?
C10 C11 . 1.529(2) ?
C11 N2 . 1.4737(18) ?
C11 C22 . 1.505(2) ?
C12 N1 . 1.4546(18) ?
C12 C13 . 1.514(2) ?
C13 C18 . 1.389(2) ?
C13 C14 . 1.4002(19) ?
C14 C15 . 1.386(2) ?
C15 C16 . 1.387(2) ?
C16 C17 . 1.388(2) ?
C17 C18 . 1.391(2) ?
C19 O2 . 1.2059(18) ?
C19 O3 . 1.3458(17) ?
C20 O3 . 1.4567(18) ?
C20 C21 . 1.497(3) ?
C22 C23 . 1.387(2) ?
C22 C27 . 1.398(2) ?
C23 C24 . 1.391(2) ?
C24 C25 . 1.389(2) ?
C25 C26 . 1.383(2) ?
C26 C27 . 1.392(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 125.36(13) ?
O1 C1 C2 . . 126.21(13) ?
N1 C1 C2 . . 108.43(12) ?
N2 C2 C3 . . 112.70(12) ?
N2 C2 C1 . . 114.01(11) ?
C3 C2 C1 . . 101.84(11) ?
N2 C2 C9 . . 103.26(10) ?
C3 C2 C9 . . 116.70(11) ?
C1 C2 C9 . . 108.71(11) ?
C4 C3 C8 . . 120.17(13) ?
C4 C3 C2 . . 130.73(13) ?
C8 C3 C2 . . 109.10(12) ?
C3 C4 C5 . . 118.65(14) ?
C6 C5 C4 . . 120.67(14) ?
C5 C6 C7 . . 121.18(14) ?
C8 C7 C6 . . 117.15(14) ?
C7 C8 C3 . . 122.18(13) ?
C7 C8 N1 . . 128.20(13) ?
C3 C8 N1 . . 109.62(12) ?
C19 C9 C10 . . 115.16(12) ?
C19 C9 C2 . . 114.24(12) ?
C10 C9 C2 . . 104.21(11) ?
C9 C10 C11 . . 101.39(11) ?
N2 C11 C22 . . 114.62(12) ?
N2 C11 C10 . . 100.74(11) ?
C22 C11 C10 . . 111.72(12) ?
N1 C12 C13 . . 114.30(12) ?
C18 C13 C14 . . 118.82(14) ?
C18 C13 C12 . . 122.45(13) ?
C14 C13 C12 . . 118.71(13) ?
C15 C14 C13 . . 120.25(14) ?
C14 C15 C16 . . 120.56(14) ?
C15 C16 C17 . . 119.55(15) ?
C16 C17 C18 . . 120.04(15) ?
C13 C18 C17 . . 120.78(14) ?
O2 C19 O3 . . 124.35(14) ?
O2 C19 C9 . . 125.65(13) ?
O3 C19 C9 . . 109.97(12) ?
O3 C20 C21 . . 111.31(14) ?
C23 C22 C27 . . 118.86(14) ?
C23 C22 C11 . . 122.62(13) ?
C27 C22 C11 . . 118.28(13) ?
C22 C23 C24 . . 120.31(15) ?
C25 C24 C23 . . 120.47(15) ?
C26 C25 C24 . . 119.69(14) ?
C25 C26 C27 . . 119.84(14) ?
C26 C27 C22 . . 120.79(14) ?
C1 N1 C8 . . 111.00(11) ?
C1 N1 C12 . . 123.48(13) ?
C8 N1 C12 . . 125.52(12) ?
C11 N2 C2 . . 109.28(11) ?
C19 O3 C20 . . 117.11(12) ?


####################################################################### 
# 
# 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_chiba398
_database_code_depnum_ccdc_archive 'CCDC 1436815'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         297.34

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.9415(12)
_cell_length_b                   14.8517(12)
_cell_length_c                   6.2573(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1481.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5625
_cell_measurement_theta_min      2.5553
_cell_measurement_theta_max      21.4327
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            31046
_diffrn_reflns_av_R_equivalents  0.1227
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_special_details          
;
;

_reflns_number_total             1370
_reflns_number_gt                765
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1308
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.955
_refine_ls_number_reflns         1370
_refine_ls_number_parameters     179
_refine_ls_number_restraints     330
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.8162P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2012(2) 0.242(3) 0.3680(7) 0.047(3) Uani d U P . 0.5 A -1
H H1A 0.1892 0.2835 0.2493 0.07 Uiso calc U P R 0.5 A -1
H H1B 0.1693 0.2612 0.4943 0.07 Uiso calc U P R 0.5 A -1
H H1C 0.1849 0.1811 0.3279 0.07 Uiso calc U P R 0.5 A -1
C C2 0.3422(2) 0.247(3) 0.2475(5) 0.0432(18) Uani d U P . 0.5 A -1
C C3 0.4342(2) 0.2555(14) 0.3164(5) 0.0498(14) Uani d U P D 0.5 A -1
C C4 0.4508(9) 0.3322(9) 0.4801(18) 0.050(2) Uani d U P D 0.5 A -1
H H4 0.5129 0.3418 0.4772 0.06 Uiso calc U P R 0.5 A -1
C C5 0.4126(7) 0.4234(7) 0.4156(19) 0.057(3) Uani d U P DG 0.5 A -1
C C6 0.4387(5) 0.4748(8) 0.2423(17) 0.061(3) Uani d U P G 0.5 A -1
H H6 0.4832 0.454 0.1539 0.074 Uiso calc U P R 0.5 A -1
C C7 0.3998(6) 0.5564(8) 0.1982(17) 0.069(3) Uani d U P G 0.5 A -1
H H7 0.4177 0.5915 0.0797 0.083 Uiso calc U P R 0.5 A -1
C C8 0.3348(7) 0.5868(7) 0.3274(18) 0.066(3) Uani d U P G 0.5 A -1
H H8 0.3082 0.6426 0.2973 0.08 Uiso calc U P R 0.5 A -1
C C9 0.3086(6) 0.5354(9) 0.5008(14) 0.056(3) Uani d U P G 0.5 A -1
H H9 0.2642 0.5562 0.5891 0.068 Uiso calc U P R 0.5 A -1
C C10 0.3475(7) 0.4537(9) 0.5449(14) 0.058(3) Uani d U P G 0.5 A -1
H H10 0.3296 0.4186 0.6633 0.069 Uiso calc U P R 0.5 A -1
C C11 0.4688(6) 0.1967(7) 0.6752(15) 0.065(3) Uani d U P D 0.5 A -1
H H11A 0.4369 0.1539 0.7652 0.078 Uiso calc U P R 0.5 A -1
H H11B 0.528 0.1968 0.723 0.078 Uiso calc U P R 0.5 A -1
C C12 0.4632(10) 0.1694(9) 0.4398(18) 0.054(3) Uani d U P D 0.5 A -1
H H12 0.521 0.1538 0.3898 0.065 Uiso calc U P R 0.5 A -1
C C13 0.4089(7) 0.0848(7) 0.4230(18) 0.049(3) Uani d U P DG 0.5 A -1
C C14 0.4161(5) 0.0396(7) 0.2293(16) 0.051(2) Uani d U P G 0.5 A -1
H H14 0.4485 0.0648 0.1169 0.061 Uiso calc U P R 0.5 A -1
C C15 0.3758(6) -0.0425(7) 0.2001(15) 0.060(3) Uani d U P G 0.5 A -1
H H15 0.3808 -0.0734 0.0677 0.072 Uiso calc U P R 0.5 A -1
C C16 0.3284(7) -0.0794(7) 0.3646(17) 0.059(3) Uani d U P G 0.5 A -1
H H16 0.3009 -0.1356 0.3446 0.071 Uiso calc U P R 0.5 A -1
C C17 0.3212(7) -0.0343(8) 0.5583(14) 0.056(3) Uani d U P G 0.5 A -1
H H17 0.2888 -0.0595 0.6707 0.067 Uiso calc U P R 0.5 A -1
C C18 0.3614(7) 0.0478(8) 0.5875(14) 0.053(2) Uani d U P G 0.5 A -1
H H18 0.3565 0.0787 0.7198 0.064 Uiso calc U P R 0.5 A -1
N N1 0.4333(4) 0.2867(5) 0.6923(11) 0.055(2) Uani d U P D 0.5 A -1
H H1N 0.3794(17) 0.274(4) 0.704(8) 0.082 Uiso d U P D 0.5 B -1
O O1 0.48513(18) 0.2699(5) 0.1327(4) 0.045(3) Uani d U P . 0.5 A -1
H H1 0.455 0.2688 0.0225 0.068 Uiso calc U P R 0.5 A -1
O O2 0.31841(18) 0.242(7) 0.0666(4) 0.054(8) Uani d U P . 0.5 A -1
O O3 0.29037(17) 0.245(4) 0.4164(4) 0.043(4) Uani d U P . 0.5 A -1


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O3 . 1.454(5) ?
C2 O2 . 1.195(6) ?
C2 O3 . 1.342(5) ?
C2 C3 . 1.534(7) ?
C3 O1 . 1.424(5) ?
C3 C4 . 1.554(10) ?
C3 C12 . 1.564(11) ?
C4 N1 . 1.515(12) ?
C4 C5 . 1.540(11) ?
C5 C6 . 1.39 ?
C5 C10 . 1.39 ?
C6 C7 . 1.39 ?
C7 C8 . 1.39 ?
C8 C9 . 1.39 ?
C9 C10 . 1.39 ?
C11 N1 . 1.455(9) ?
C11 C12 . 1.530(11) ?
C12 C13 . 1.530(10) ?
C13 C14 . 1.39 ?
C13 C18 . 1.39 ?
C14 C15 . 1.39 ?
C15 C16 . 1.39 ?
C16 C17 . 1.39 ?
C17 C18 . 1.39 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C2 O3 . . 123.3(4) ?
O2 C2 C3 . . 125.0(4) ?
O3 C2 C3 . . 111.7(4) ?
O1 C3 C2 . . 109.3(4) ?
O1 C3 C4 . . 109.0(10) ?
C2 C3 C4 . . 114.1(17) ?
O1 C3 C12 . . 110.6(9) ?
C2 C3 C12 . . 111.(2) ?
C4 C3 C12 . . 102.9(3) ?
N1 C4 C5 . . 123.3(9) ?
N1 C4 C3 . . 102.7(8) ?
C5 C4 C3 . . 113.8(12) ?
C6 C5 C10 . . 120.0 ?
C6 C5 C4 . . 124.7(8) ?
C10 C5 C4 . . 115.3(8) ?
C7 C6 C5 . . 120.0 ?
C8 C7 C6 . . 120.0 ?
C7 C8 C9 . . 120.0 ?
C10 C9 C8 . . 120.0 ?
C9 C10 C5 . . 120.0 ?
N1 C11 C12 . . 106.9(11) ?
C11 C12 C13 . . 108.5(9) ?
C11 C12 C3 . . 106.0(8) ?
C13 C12 C3 . . 118.1(13) ?
C14 C13 C18 . . 120.0 ?
C14 C13 C12 . . 114.2(8) ?
C18 C13 C12 . . 125.5(8) ?
C13 C14 C15 . . 120.0 ?
C14 C15 C16 . . 120.0 ?
C17 C16 C15 . . 120.0 ?
C16 C17 C18 . . 120.0 ?
C17 C18 C13 . . 120.0 ?
C11 N1 C4 . . 105.8(9) ?
C2 O3 C1 . . 116.0(3) ?


