# 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_m20151113b
_database_code_depnum_ccdc_archive 'CCDC 1498693'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32

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                   8.5064(9)
_cell_length_b                   17.8133(19)
_cell_length_c                   9.4824(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.126(3)
_cell_angle_gamma                90
_cell_volume                     1418.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4505
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            18579
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         28.737
_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             3671
_reflns_number_gt                3307
_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       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+0.4807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3671
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37069(9) 0.57921(5) 0.53872(9) 0.02087(19) Uani 1 1 d . . . . .
O2 O 0.41427(10) 0.77752(5) 0.68871(10) 0.0266(2) Uani 1 1 d . . . . .
O3 O 0.64620(10) 0.83974(5) 0.71962(10) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.61785(11) 0.62854(5) 0.56957(9) 0.01483(19) Uani 1 1 d . . . . .
N2 N 0.29758(13) 0.50664(6) 0.85732(12) 0.0246(2) Uani 1 1 d . . . . .
C1 C 0.64506(14) 0.60503(6) 0.42502(12) 0.0191(2) Uani 1 1 d . . . . .
H1A H 0.6180 0.6460 0.3549 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5807 0.5602 0.3922 0.023 Uiso 1 1 calc R U . . .
C2 C 0.82391(14) 0.58705(6) 0.44532(13) 0.0203(2) Uani 1 1 d . . . . .
H2A H 0.8431 0.5325 0.4583 0.024 Uiso 1 1 calc R U . . .
H2B H 0.8720 0.6046 0.3627 0.024 Uiso 1 1 calc R U . . .
C3 C 0.88975(13) 0.62988(6) 0.57894(12) 0.0172(2) Uani 1 1 d . . . . .
C4 C 0.76448(12) 0.65240(5) 0.64810(11) 0.0142(2) Uani 1 1 d . . . . .
C5 C 0.78791(12) 0.69526(5) 0.77177(11) 0.0143(2) Uani 1 1 d . . . . .
C6 C 0.94505(13) 0.71239(6) 0.83031(12) 0.0178(2) Uani 1 1 d . . . . .
H6 H 0.9657 0.7410 0.9158 0.021 Uiso 1 1 calc R U . . .
C7 C 1.07157(13) 0.68824(6) 0.76536(13) 0.0210(2) Uani 1 1 d . . . . .
H7 H 1.1775 0.6999 0.8077 0.025 Uiso 1 1 calc R U . . .
C8 C 1.04464(13) 0.64697(6) 0.63835(13) 0.0209(2) Uani 1 1 d . . . . .
H8 H 1.1313 0.6310 0.5937 0.025 Uiso 1 1 calc R U . . .
C9 C 0.64792(12) 0.72417(6) 0.83637(11) 0.0139(2) Uani 1 1 d . . . . .
H9 H 0.6920 0.7503 0.9274 0.017 Uiso 1 1 calc R U . . .
C10 C 0.54441(12) 0.66059(6) 0.87423(11) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.47814(12) 0.61001(6) 0.77629(11) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.48405(12) 0.60608(6) 0.61913(11) 0.0148(2) Uani 1 1 d . . . . .
C13 C 0.55253(12) 0.78256(6) 0.73820(11) 0.0148(2) Uani 1 1 d . . . . .
C14 C 0.57897(14) 0.90351(6) 0.63317(13) 0.0213(2) Uani 1 1 d . . . . .
H14A H 0.4632 0.9075 0.6350 0.026 Uiso 1 1 calc R U . . .
H14B H 0.5955 0.8971 0.5328 0.026 Uiso 1 1 calc R U . . .
C15 C 0.66275(19) 0.97245(7) 0.69613(15) 0.0323(3) Uani 1 1 d . . . . .
H15A H 0.6212 1.0165 0.6403 0.039 Uiso 1 1 calc R U . . .
H15B H 0.7772 0.9677 0.6942 0.039 Uiso 1 1 calc R U . . .
H15C H 0.6448 0.9784 0.7951 0.039 Uiso 1 1 calc R U . . .
C16 C 0.51878(15) 0.65860(6) 1.02648(12) 0.0204(2) Uani 1 1 d . . . . .
H16A H 0.4609 0.6128 1.0435 0.024 Uiso 1 1 calc R U . . .
H16B H 0.4567 0.7026 1.0464 0.024 Uiso 1 1 calc R U . . .
H16C H 0.6220 0.6591 1.0893 0.024 Uiso 1 1 calc R U . . .
C17 C 0.37659(13) 0.55240(6) 0.82062(12) 0.0171(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.2277(13) . ?
O2 C13 1.1985(13) . ?
O3 C13 1.3222(13) . ?
O3 C14 1.4631(13) . ?
N1 C12 1.3587(14) . ?
N1 C4 1.4128(13) . ?
N1 C1 1.4861(14) . ?
N2 C17 1.1453(15) . ?
C1 C2 1.5366(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5086(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.3823(16) . ?
C3 C4 1.3958(15) . ?
C4 C5 1.3870(14) . ?
C5 C6 1.3973(14) . ?
C5 C9 1.5132(14) . ?
C6 C7 1.3903(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3986(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.5123(14) . ?
C9 C13 1.5385(14) . ?
C9 H9 1.0000 . ?
C10 C11 1.3513(14) . ?
C10 C16 1.4943(15) . ?
C11 C17 1.4461(15) . ?
C11 C12 1.5007(15) . ?
C14 C15 1.4959(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O3 C14 118.85(9) . . ?
C12 N1 C4 128.62(9) . . ?
C12 N1 C1 119.84(9) . . ?
C4 N1 C1 108.50(8) . . ?
N1 C1 C2 103.83(9) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 C1 103.19(9) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C8 C3 C4 119.65(10) . . ?
C8 C3 C2 131.04(10) . . ?
C4 C3 C2 109.30(9) . . ?
C5 C4 C3 122.51(10) . . ?
C5 C4 N1 127.42(9) . . ?
C3 C4 N1 109.99(9) . . ?
C4 C5 C6 117.14(10) . . ?
C4 C5 C9 120.85(9) . . ?
C6 C5 C9 121.97(9) . . ?
C7 C6 C5 121.03(10) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.76(10) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 118.82(10) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C5 111.50(8) . . ?
C10 C9 C13 112.26(8) . . ?
C5 C9 C13 111.00(8) . . ?
C10 C9 H9 107.3 . . ?
C5 C9 H9 107.3 . . ?
C13 C9 H9 107.3 . . ?
C11 C10 C16 122.64(10) . . ?
C11 C10 C9 122.09(9) . . ?
C16 C10 C9 115.26(9) . . ?
C10 C11 C17 118.47(10) . . ?
C10 C11 C12 129.61(10) . . ?
C17 C11 C12 111.79(9) . . ?
O1 C12 N1 121.23(10) . . ?
O1 C12 C11 119.23(10) . . ?
N1 C12 C11 119.45(9) . . ?
O2 C13 O3 125.46(10) . . ?
O2 C13 C9 125.24(10) . . ?
O3 C13 C9 109.29(9) . . ?
O3 C14 C15 107.13(10) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C11 179.10(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -139.81(10) . . . . ?
C4 N1 C1 C2 22.13(11) . . . . ?
N1 C1 C2 C3 -21.37(11) . . . . ?
C1 C2 C3 C8 -167.22(11) . . . . ?
C1 C2 C3 C4 14.18(11) . . . . ?
C8 C3 C4 C5 3.56(16) . . . . ?
C2 C3 C4 C5 -177.65(9) . . . . ?
C8 C3 C4 N1 -179.49(9) . . . . ?
C2 C3 C4 N1 -0.71(12) . . . . ?
C12 N1 C4 C5 -37.29(16) . . . . ?
C1 N1 C4 C5 162.84(10) . . . . ?
C12 N1 C4 C3 145.95(10) . . . . ?
C1 N1 C4 C3 -13.91(11) . . . . ?
C3 C4 C5 C6 -3.22(15) . . . . ?
N1 C4 C5 C6 -179.61(9) . . . . ?
C3 C4 C5 C9 174.67(9) . . . . ?
N1 C4 C5 C9 -1.72(16) . . . . ?
C4 C5 C6 C7 0.99(15) . . . . ?
C9 C5 C6 C7 -176.88(10) . . . . ?
C5 C6 C7 C8 0.89(17) . . . . ?
C4 C3 C8 C7 -1.53(16) . . . . ?
C2 C3 C8 C7 179.99(11) . . . . ?
C6 C7 C8 C3 -0.61(17) . . . . ?
C4 C5 C9 C10 59.07(12) . . . . ?
C6 C5 C9 C10 -123.14(10) . . . . ?
C4 C5 C9 C13 -66.89(12) . . . . ?
C6 C5 C9 C13 110.90(11) . . . . ?
C5 C9 C10 C11 -56.89(12) . . . . ?
C13 C9 C10 C11 68.38(12) . . . . ?
C5 C9 C10 C16 124.07(10) . . . . ?
C13 C9 C10 C16 -110.66(10) . . . . ?
C16 C10 C11 C17 0.92(15) . . . . ?
C9 C10 C11 C17 -178.05(9) . . . . ?
C16 C10 C11 C12 176.41(10) . . . . ?
C9 C10 C11 C12 -2.55(17) . . . . ?
C4 N1 C12 O1 -172.14(10) . . . . ?
C1 N1 C12 O1 -14.24(15) . . . . ?
C4 N1 C12 C11 4.29(15) . . . . ?
C1 N1 C12 C11 162.19(9) . . . . ?
C10 C11 C12 O1 -149.03(11) . . . . ?
C17 C11 C12 O1 26.71(13) . . . . ?
C10 C11 C12 N1 34.47(16) . . . . ?
C17 C11 C12 N1 -149.79(9) . . . . ?
C14 O3 C13 O2 0.64(17) . . . . ?
C14 O3 C13 C9 -178.03(9) . . . . ?
C10 C9 C13 O2 -4.29(15) . . . . ?
C5 C9 C13 O2 121.25(12) . . . . ?
C10 C9 C13 O3 174.39(9) . . . . ?
C5 C9 C13 O3 -60.07(11) . . . . ?
C13 O3 C14 C15 146.29(11) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_m20160126c
_database_code_depnum_ccdc_archive 'CCDC 1498694'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_date             2016-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   9.2814(19)
_cell_length_b                   10.2730(19)
_cell_length_c                   11.8447(19)
_cell_angle_alpha                79.305(11)
_cell_angle_beta                 79.574(12)
_cell_angle_gamma                83.084(12)
_cell_volume                     1087.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3094
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14022
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.076
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9829
	          2theta: -15.0831
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9829
	          2theta: -15.0831
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9829
	          2theta: -15.0831
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.102785
_diffrn_orient_matrix_UB_12      0.027295
_diffrn_orient_matrix_UB_13      0.028095
_diffrn_orient_matrix_UB_21      -0.000178
_diffrn_orient_matrix_UB_22      -0.086757
_diffrn_orient_matrix_UB_23      0.048647
_diffrn_orient_matrix_UB_31      0.043777
_diffrn_orient_matrix_UB_32      0.048795
_diffrn_orient_matrix_UB_33      0.057315
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4059
_reflns_number_total             4895
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.9818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.29009(16) 0.56226(15) 0.72010(13) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.59719(15) 0.74684(14) 0.83858(13) 0.0293(3) Uani 1 1 d . . . . .
O3 O 0.74133(18) 1.27565(14) 0.57174(14) 0.0347(3) Uani 1 1 d . . . . .
O4 O 0.58703(17) 1.12410(14) 0.57210(14) 0.0349(4) Uani 1 1 d . . . . .
N1 N 1.13662(18) 0.75144(16) 0.72989(14) 0.0242(3) Uani 1 1 d . . . . .
N2 N 1.1679(2) 0.37276(18) 0.54402(16) 0.0306(4) Uani 1 1 d . . . . .
C1 C 1.2448(2) 0.8303(2) 0.75957(19) 0.0296(4) Uani 1 1 d . . . . .
H1A H 1.346938 0.793078 0.735632 0.036 Uiso 1 1 calc R . . . .
H1B H 1.228446 0.832472 0.844164 0.036 Uiso 1 1 calc R . . . .
C2 C 1.2143(2) 0.9697(2) 0.68955(18) 0.0292(4) Uani 1 1 d . . . . .
H2A H 1.224503 1.039940 0.733859 0.035 Uiso 1 1 calc R . . . .
H2B H 1.281680 0.982567 0.614134 0.035 Uiso 1 1 calc R . . . .
C3 C 1.0573(2) 0.97013(19) 0.67188(16) 0.0249(4) Uani 1 1 d . . . . .
C4 C 0.9587(2) 1.07372(19) 0.63778(16) 0.0253(4) Uani 1 1 d . . . . .
H4 H 0.985641 1.162444 0.620333 0.030 Uiso 1 1 calc R . . . .
C5 C 0.8169(2) 1.04631(19) 0.62908(16) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.7748(2) 0.91714(19) 0.65860(16) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.677359 0.901644 0.654007 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8738(2) 0.80889(18) 0.69515(16) 0.0221(4) Uani 1 1 d . . . . .
C8 C 1.0163(2) 0.83951(18) 0.69662(16) 0.0224(4) Uani 1 1 d . . . . .
C9 C 1.1778(2) 0.62871(19) 0.70006(16) 0.0232(4) Uani 1 1 d . . . . .
C10 C 1.0660(2) 0.58468(18) 0.63568(16) 0.0213(4) Uani 1 1 d . . . . .
H10 H 1.047762 0.658018 0.570057 0.026 Uiso 1 1 calc R . . . .
C11 C 0.9201(2) 0.56412(18) 0.71601(15) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.8287(2) 0.67259(18) 0.73672(16) 0.0213(4) Uani 1 1 d . . . . .
C13 C 0.6797(2) 0.65382(19) 0.80698(16) 0.0228(4) Uani 1 1 d . . . . .
C14 C 0.6352(2) 0.51323(19) 0.83520(18) 0.0262(4) Uani 1 1 d . . . . .
H14A H 0.601937 0.491488 0.766611 0.031 Uiso 1 1 calc R . . . .
H14B H 0.551312 0.507395 0.900229 0.031 Uiso 1 1 calc R . . . .
C15 C 0.7611(2) 0.41090(19) 0.86905(17) 0.0248(4) Uani 1 1 d . . . . .
C16 C 0.8868(2) 0.42321(18) 0.76515(17) 0.0237(4) Uani 1 1 d . . . . .
H16A H 0.976631 0.372344 0.789809 0.028 Uiso 1 1 calc R . . . .
H16B H 0.861036 0.382311 0.702913 0.028 Uiso 1 1 calc R . . . .
C17 C 0.8129(3) 0.4383(2) 0.97782(18) 0.0321(5) Uani 1 1 d . . . . .
H17A H 0.730733 0.433507 1.042916 0.048 Uiso 1 1 calc GR . . . .
H17B H 0.847825 0.527255 0.961898 0.048 Uiso 1 1 calc GR . . . .
H17C H 0.893091 0.371756 0.998005 0.048 Uiso 1 1 calc GR . . . .
C18 C 0.7111(3) 0.2705(2) 0.8932(2) 0.0340(5) Uani 1 1 d . . . . .
H18A H 0.634171 0.261460 0.962042 0.051 Uiso 1 1 calc GR . . . .
H18B H 0.794905 0.205416 0.907127 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.672043 0.254724 0.825847 0.051 Uiso 1 1 calc GR . . . .
C19 C 1.1282(2) 0.46550(19) 0.58522(17) 0.0239(4) Uani 1 1 d . . . . .
C20 C 0.7137(2) 1.16050(19) 0.58902(17) 0.0260(4) Uani 1 1 d . . . . .
C21 C 0.4814(3) 1.2330(2) 0.5355(2) 0.0385(5) Uani 1 1 d . . . . .
H21A H 0.452499 1.287927 0.596626 0.058 Uiso 1 1 calc GR . . . .
H21B H 0.394325 1.197048 0.521410 0.058 Uiso 1 1 calc GR . . . .
H21C H 0.526106 1.287424 0.463627 0.058 Uiso 1 1 calc GR . . . .


_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 C9 1.211(2) . ?
O2 C13 1.222(2) . ?
O3 C20 1.213(2) . ?
O4 C20 1.334(3) . ?
O4 C21 1.453(3) . ?
N1 C1 1.489(2) . ?
N1 C8 1.416(2) . ?
N1 C9 1.364(3) . ?
N2 C19 1.142(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.538(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(3) . ?
C3 C4 1.369(3) . ?
C3 C8 1.403(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(3) . ?
C5 C6 1.392(3) . ?
C5 C20 1.486(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.479(3) . ?
C9 C10 1.546(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.520(3) . ?
C10 C19 1.472(3) . ?
C11 C12 1.349(3) . ?
C11 C16 1.503(3) . ?
C12 C13 1.494(3) . ?
C13 C14 1.511(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.532(3) . ?
C15 C16 1.533(3) . ?
C15 C17 1.537(3) . ?
C15 C18 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
C20 O4 C21 115.13(17) . . ?
C8 N1 C1 108.52(15) . . ?
C9 N1 C1 121.19(16) . . ?
C9 N1 C8 126.17(16) . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.37(16) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 102.80(16) . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C4 C3 C2 130.30(18) . . ?
C4 C3 C8 120.05(18) . . ?
C8 C3 C2 109.65(17) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.71(18) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C20 117.40(17) . . ?
C6 C5 C4 120.99(18) . . ?
C6 C5 C20 121.60(19) . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.39(18) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C12 122.56(17) . . ?
C8 C7 C6 115.79(17) . . ?
C8 C7 C12 121.54(17) . . ?
C3 C8 N1 109.13(17) . . ?
C7 C8 N1 127.82(17) . . ?
C7 C8 C3 122.90(18) . . ?
O1 C9 N1 124.00(18) . . ?
O1 C9 C10 123.63(18) . . ?
N1 C9 C10 112.36(16) . . ?
C9 C10 H10 107.7 . . ?
C11 C10 C9 110.75(15) . . ?
C11 C10 H10 107.7 . . ?
C19 C10 C9 110.28(16) . . ?
C19 C10 H10 107.7 . . ?
C19 C10 C11 112.42(16) . . ?
C12 C11 C10 118.15(16) . . ?
C12 C11 C16 124.54(17) . . ?
C16 C11 C10 117.29(16) . . ?
C7 C12 C13 119.29(16) . . ?
C11 C12 C7 121.87(17) . . ?
C11 C12 C13 118.81(17) . . ?
O2 C13 C12 122.13(17) . . ?
O2 C13 C14 121.64(18) . . ?
C12 C13 C14 116.23(16) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C13 C14 C15 112.52(16) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 C16 106.85(15) . . ?
C14 C15 C17 110.83(17) . . ?
C16 C15 C17 110.15(17) . . ?
C18 C15 C14 110.16(17) . . ?
C18 C15 C16 109.59(16) . . ?
C18 C15 C17 109.23(17) . . ?
C11 C16 C15 113.87(16) . . ?
C11 C16 H16A 108.8 . . ?
C11 C16 H16B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C10 175.6(2) . . ?
O3 C20 O4 122.84(19) . . ?
O3 C20 C5 123.83(19) . . ?
O4 C20 C5 113.33(17) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 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
O1 C9 C10 C11 114.9(2) . . . . ?
O1 C9 C10 C19 -10.2(3) . . . . ?
O2 C13 C14 C15 -139.54(19) . . . . ?
N1 C1 C2 C3 23.7(2) . . . . ?
N1 C9 C10 C11 -66.1(2) . . . . ?
N1 C9 C10 C19 168.82(16) . . . . ?
C1 N1 C8 C3 16.2(2) . . . . ?
C1 N1 C8 C7 -159.34(19) . . . . ?
C1 N1 C9 O1 17.5(3) . . . . ?
C1 N1 C9 C10 -161.54(16) . . . . ?
C1 C2 C3 C4 164.6(2) . . . . ?
C1 C2 C3 C8 -15.3(2) . . . . ?
C2 C3 C4 C5 -179.45(19) . . . . ?
C2 C3 C8 N1 0.0(2) . . . . ?
C2 C3 C8 C7 175.85(18) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C3 C4 C5 C20 -178.52(17) . . . . ?
C4 C3 C8 N1 -179.88(17) . . . . ?
C4 C3 C8 C7 -4.0(3) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C4 C5 C20 O3 -5.5(3) . . . . ?
C4 C5 C20 O4 173.65(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C5 C6 C7 C12 174.58(17) . . . . ?
C6 C5 C20 O3 173.61(19) . . . . ?
C6 C5 C20 O4 -7.3(3) . . . . ?
C6 C7 C8 N1 179.56(18) . . . . ?
C6 C7 C8 C3 4.5(3) . . . . ?
C6 C7 C12 C11 145.50(19) . . . . ?
C6 C7 C12 C13 -36.5(3) . . . . ?
C7 C12 C13 O2 -5.3(3) . . . . ?
C7 C12 C13 C14 173.60(16) . . . . ?
C8 N1 C1 C2 -25.1(2) . . . . ?
C8 N1 C9 O1 171.98(19) . . . . ?
C8 N1 C9 C10 -7.0(3) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C8 C7 C12 C11 -38.5(3) . . . . ?
C8 C7 C12 C13 139.45(18) . . . . ?
C9 N1 C1 C2 133.40(18) . . . . ?
C9 N1 C8 C3 -140.92(19) . . . . ?
C9 N1 C8 C7 43.5(3) . . . . ?
C9 C10 C11 C12 77.9(2) . . . . ?
C9 C10 C11 C16 -103.21(19) . . . . ?
C10 C11 C12 C7 -7.3(3) . . . . ?
C10 C11 C12 C13 174.75(15) . . . . ?
C10 C11 C16 C15 164.19(16) . . . . ?
C11 C12 C13 O2 172.67(18) . . . . ?
C11 C12 C13 C14 -8.4(3) . . . . ?
C12 C7 C8 N1 3.3(3) . . . . ?
C12 C7 C8 C3 -171.72(17) . . . . ?
C12 C11 C16 C15 -17.0(3) . . . . ?
C12 C13 C14 C15 41.5(2) . . . . ?
C13 C14 C15 C16 -59.4(2) . . . . ?
C13 C14 C15 C17 60.6(2) . . . . ?
C13 C14 C15 C18 -178.38(17) . . . . ?
C14 C15 C16 C11 46.9(2) . . . . ?
C16 C11 C12 C7 173.93(17) . . . . ?
C16 C11 C12 C13 -4.0(3) . . . . ?
C17 C15 C16 C11 -73.6(2) . . . . ?
C18 C15 C16 C11 166.21(17) . . . . ?
C19 C10 C11 C12 -158.21(17) . . . . ?
C19 C10 C11 C16 20.7(2) . . . . ?
C20 C5 C6 C7 179.19(17) . . . . ?
C21 O4 C20 O3 -2.2(3) . . . . ?
C21 O4 C20 C5 178.63(17) . . . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
