# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_282
_database_code_depnum_ccdc_archive 'CCDC 1479824'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N3 O4'
_chemical_formula_sum            'C19 H19 N3 O4'
_chemical_formula_weight         353.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   10.7611(3)
_cell_length_b                   13.0931(3)
_cell_length_c                   12.5506(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.8208(11)
_cell_angle_gamma                90
_cell_volume                     1692.67(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.28

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11183
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3456
_reflns_number_gt                2646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.3561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0099(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.30381(15) 0.44136(13) 0.92926(15) 0.0540(4) Uani 1 1 d . . . . .
H1 H 1.3323 0.5047 0.9603 0.065 Uiso 1 1 calc R U . . .
C2 C 1.37986(17) 0.35972(15) 0.92402(16) 0.0604(5) Uani 1 1 d . . . . .
H2 H 1.4698 0.3554 0.9503 0.073 Uiso 1 1 calc R U . . .
C3 C 1.29401(16) 0.28444(13) 0.87097(14) 0.0532(4) Uani 1 1 d . . . . .
H3 H 1.3192 0.2193 0.8562 0.064 Uiso 1 1 calc R U . . .
C4 C 1.06818(13) 0.47828(10) 0.85025(11) 0.0361(3) Uani 1 1 d . . . . .
C5 C 0.94910(13) 0.44711(10) 0.86429(11) 0.0356(3) Uani 1 1 d . . . . .
C6 C 0.84397(14) 0.51327(11) 0.82726(13) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.7635 0.4946 0.8348 0.053 Uiso 1 1 calc R U . . .
C7 C 0.85743(16) 0.60624(12) 0.77952(14) 0.0486(4) Uani 1 1 d . . . . .
H7 H 0.7857 0.6489 0.7547 0.058 Uiso 1 1 calc R U . . .
C8 C 0.97551(16) 0.63664(11) 0.76823(13) 0.0466(4) Uani 1 1 d . . . . .
H8 H 0.9843 0.6999 0.7375 0.056 Uiso 1 1 calc R U . . .
C9 C 1.08003(15) 0.57201(11) 0.80319(12) 0.0424(4) Uani 1 1 d . . . . .
H9 H 1.1599 0.5916 0.7951 0.051 Uiso 1 1 calc R U . . .
C10 C 0.83727(13) 0.31145(11) 0.94011(12) 0.0374(3) Uani 1 1 d . . . . .
C11 C 0.85751(13) 0.21467(10) 1.00597(11) 0.0343(3) Uani 1 1 d . . . . .
C12 C 0.97378(13) 0.16244(11) 1.05171(12) 0.0366(3) Uani 1 1 d . . . . .
C13 C 0.97730(13) 0.07544(11) 1.11636(12) 0.0398(3) Uani 1 1 d . . . . .
H13 H 1.0556 0.0415 1.1463 0.048 Uiso 1 1 calc R U . . .
C14 C 0.86574(14) 0.03908(10) 1.13636(12) 0.0369(3) Uani 1 1 d . . . . .
C15 C 0.74761(13) 0.09032(11) 1.09089(12) 0.0357(3) Uani 1 1 d . . . . .
C16 C 0.74554(13) 0.17552(11) 1.02769(12) 0.0365(3) Uani 1 1 d . . . . .
H16 H 0.6669 0.2090 0.9978 0.044 Uiso 1 1 calc R U . . .
C17 C 1.20604(14) 0.15740(14) 1.08901(16) 0.0552(5) Uani 1 1 d . . . . .
H17A H 1.2167 0.1600 1.1676 0.083 Uiso 1 1 calc R U . . .
H17B H 1.2738 0.1961 1.0723 0.083 Uiso 1 1 calc R U . . .
H17C H 1.2104 0.0877 1.0665 0.083 Uiso 1 1 calc R U . . .
C18 C 0.97890(16) -0.09445(14) 1.25372(16) 0.0627(5) Uani 1 1 d . . . . .
H18A H 1.0205 -0.1184 1.2003 0.094 Uiso 1 1 calc R U . . .
H18B H 0.9617 -0.1512 1.2958 0.094 Uiso 1 1 calc R U . . .
H18C H 1.0347 -0.0467 1.3032 0.094 Uiso 1 1 calc R U . . .
C19 C 0.52472(14) 0.10438(13) 1.08144(15) 0.0515(4) Uani 1 1 d . . . . .
H19A H 0.5379 0.1711 1.1145 0.077 Uiso 1 1 calc R U . . .
H19B H 0.4592 0.0691 1.1052 0.077 Uiso 1 1 calc R U . . .
H19C H 0.4973 0.1107 1.0018 0.077 Uiso 1 1 calc R U . . .
N1 N 1.17979(11) 0.41370(9) 0.88132(10) 0.0386(3) Uani 1 1 d . . . . .
N2 N 1.17218(12) 0.31568(9) 0.84371(12) 0.0477(3) Uani 1 1 d . . . . .
N3 N 0.94186(12) 0.35282(9) 0.91602(11) 0.0396(3) Uani 1 1 d . . . . .
O1 O 0.72925(10) 0.35084(9) 0.91067(11) 0.0600(4) Uani 1 1 d . . . . .
O2 O 1.08324(9) 0.19952(8) 1.03056(10) 0.0511(3) Uani 1 1 d . . . . .
O3 O 0.85991(10) -0.04556(8) 1.19722(9) 0.0487(3) Uani 1 1 d . . . . .
O4 O 0.64266(9) 0.04847(8) 1.11513(9) 0.0467(3) Uani 1 1 d . . . . .
H1N H 1.0142(17) 0.3170(13) 0.9361(15) 0.060(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3451(19) . ?
C1 C2 1.359(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.3204(19) . ?
C3 H3 0.9300 . ?
C4 C9 1.384(2) . ?
C4 C5 1.4037(19) . ?
C4 N1 1.4277(17) . ?
C5 C6 1.3935(19) . ?
C5 N3 1.4075(18) . ?
C6 C7 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O1 1.2269(16) . ?
C10 N3 1.3596(18) . ?
C10 C11 1.4941(19) . ?
C11 C12 1.3953(18) . ?
C11 C16 1.4067(18) . ?
C12 O2 1.3692(16) . ?
C12 C13 1.393(2) . ?
C13 C14 1.3803(19) . ?
C13 H13 0.9300 . ?
C14 O3 1.3577(16) . ?
C14 C15 1.4043(19) . ?
C15 C16 1.365(2) . ?
C15 O4 1.3664(16) . ?
C16 H16 0.9300 . ?
C17 O2 1.4239(17) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.4236(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.4194(17) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 N2 1.3617(17) . ?
N3 H1N 0.881(17) . ?

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
N1 C1 C2 107.46(16) . . ?
N1 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
C1 C2 C3 104.84(15) . . ?
C1 C2 H2 127.6 . . ?
C3 C2 H2 127.6 . . ?
N2 C3 C2 112.26(15) . . ?
N2 C3 H3 123.9 . . ?
C2 C3 H3 123.9 . . ?
C9 C4 C5 120.77(13) . . ?
C9 C4 N1 117.89(12) . . ?
C5 C4 N1 121.33(12) . . ?
C6 C5 C4 117.38(13) . . ?
C6 C5 N3 123.44(13) . . ?
C4 C5 N3 119.17(12) . . ?
C7 C6 C5 121.00(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.95(14) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 118.91(14) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 120.96(14) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O1 C10 N3 122.60(13) . . ?
O1 C10 C11 119.79(12) . . ?
N3 C10 C11 117.61(12) . . ?
C12 C11 C16 117.26(13) . . ?
C12 C11 C10 127.81(12) . . ?
C16 C11 C10 114.86(12) . . ?
O2 C12 C13 121.54(12) . . ?
O2 C12 C11 117.76(12) . . ?
C13 C12 C11 120.70(12) . . ?
C14 C13 C12 120.63(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O3 C14 C13 124.62(13) . . ?
O3 C14 C15 115.77(12) . . ?
C13 C14 C15 119.61(13) . . ?
C16 C15 O4 125.55(12) . . ?
C16 C15 C14 119.15(12) . . ?
O4 C15 C14 115.30(12) . . ?
C15 C16 C11 122.64(13) . . ?
C15 C16 H16 118.7 . . ?
C11 C16 H16 118.7 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 N2 111.17(12) . . ?
C1 N1 C4 127.60(13) . . ?
N2 N1 C4 120.13(12) . . ?
C3 N2 N1 104.27(13) . . ?
C10 N3 C5 127.73(12) . . ?
C10 N3 H1N 116.4(11) . . ?
C5 N3 H1N 115.9(11) . . ?
C12 O2 C17 119.01(11) . . ?
C14 O3 C18 117.76(12) . . ?
C15 O4 C19 116.89(11) . . ?

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
N1 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 N2 0.3(2) . . . . ?
C9 C4 C5 C6 1.1(2) . . . . ?
N1 C4 C5 C6 -177.32(13) . . . . ?
C9 C4 C5 N3 -177.78(13) . . . . ?
N1 C4 C5 N3 3.8(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
N3 C5 C6 C7 178.32(14) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
C5 C4 C9 C8 -0.5(2) . . . . ?
N1 C4 C9 C8 178.00(13) . . . . ?
O1 C10 C11 C12 -176.03(15) . . . . ?
N3 C10 C11 C12 3.4(2) . . . . ?
O1 C10 C11 C16 0.8(2) . . . . ?
N3 C10 C11 C16 -179.72(13) . . . . ?
C16 C11 C12 O2 179.62(12) . . . . ?
C10 C11 C12 O2 -3.6(2) . . . . ?
C16 C11 C12 C13 -0.2(2) . . . . ?
C10 C11 C12 C13 176.55(14) . . . . ?
O2 C12 C13 C14 -179.76(14) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 O3 179.25(13) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
O3 C14 C15 C16 -179.33(12) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
O3 C14 C15 O4 0.66(19) . . . . ?
C13 C14 C15 O4 179.88(13) . . . . ?
O4 C15 C16 C11 179.97(13) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C10 C11 C16 C15 -176.98(13) . . . . ?
C2 C1 N1 N2 -0.45(19) . . . . ?
C2 C1 N1 C4 -168.28(14) . . . . ?
C9 C4 N1 C1 40.2(2) . . . . ?
C5 C4 N1 C1 -141.34(16) . . . . ?
C9 C4 N1 N2 -126.71(14) . . . . ?
C5 C4 N1 N2 51.79(18) . . . . ?
C2 C3 N2 N1 -0.58(18) . . . . ?
C1 N1 N2 C3 0.63(17) . . . . ?
C4 N1 N2 C3 169.50(13) . . . . ?
O1 C10 N3 C5 5.5(2) . . . . ?
C11 C10 N3 C5 -173.91(13) . . . . ?
C6 C5 N3 C10 -1.2(2) . . . . ?
C4 C5 N3 C10 177.67(14) . . . . ?
C13 C12 O2 C17 -9.4(2) . . . . ?
C11 C12 O2 C17 170.79(14) . . . . ?
C13 C14 O3 C18 6.7(2) . . . . ?
C15 C14 O3 C18 -174.14(14) . . . . ?
C16 C15 O4 C19 -7.0(2) . . . . ?
C14 C15 O4 C19 173.04(13) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_302
_database_code_depnum_ccdc_archive 'CCDC 1479825'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.098(2)
_cell_length_b                   8.3128(11)
_cell_length_c                   31.328(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3150.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11977
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.300
_diffrn_reflns_theta_max         20.891
_diffrn_reflns_theta_full        20.891
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1670
_reflns_number_gt                1141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.5653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1660
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7847(3) 0.3248(4) 0.26648(12) 0.0545(10) Uani 1 1 d . . . . .
H1 H 0.7218 0.2616 0.2698 0.065 Uiso 1 1 calc R U . . .
C2 C 0.8019(3) 0.4058(5) 0.22858(13) 0.0637(11) Uani 1 1 d . . . . .
H2 H 0.7500 0.3985 0.2068 0.076 Uiso 1 1 calc R U . . .
C3 C 0.8954(4) 0.4973(4) 0.22289(13) 0.0639(11) Uani 1 1 d . . . . .
H3 H 0.9069 0.5510 0.1972 0.077 Uiso 1 1 calc R U . . .
C4 C 0.9714(3) 0.5091(4) 0.25498(13) 0.0576(10) Uani 1 1 d . . . . .
H4 H 1.0353 0.5694 0.2509 0.069 Uiso 1 1 calc R U . . .
C5 C 0.9538(3) 0.4317(4) 0.29343(11) 0.0423(9) Uani 1 1 d . . . . .
C6 C 0.8601(3) 0.3366(4) 0.29964(11) 0.0417(9) Uani 1 1 d . . . . .
C7 C 0.7462(3) 0.2138(4) 0.35598(11) 0.0471(10) Uani 1 1 d . . . . .
C8 C 0.7455(3) 0.1112(4) 0.39560(11) 0.0430(9) Uani 1 1 d . . . . .
C9 C 0.8369(3) 0.0476(4) 0.41681(12) 0.0483(10) Uani 1 1 d . . . . .
C10 C 0.8230(3) -0.0451(4) 0.45305(12) 0.0565(11) Uani 1 1 d . . . . .
H10 H 0.8838 -0.0866 0.4675 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7171(4) -0.0749(4) 0.46743(12) 0.0570(10) Uani 1 1 d . . . . .
C12 C 0.6249(3) -0.0166(5) 0.44766(13) 0.0626(11) Uani 1 1 d . . . . .
H12 H 0.5543 -0.0384 0.4579 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6413(3) 0.0757(4) 0.41186(12) 0.0546(10) Uani 1 1 d . . . . .
H13 H 0.5797 0.1165 0.3978 0.066 Uiso 1 1 calc R U . . .
C14 C 1.0797(3) 0.6018(4) 0.33689(13) 0.0545(10) Uani 1 1 d . . . . .
H14 H 1.0690 0.6997 0.3231 0.065 Uiso 1 1 calc R U . . .
C15 C 1.1466(3) 0.5739(5) 0.37086(14) 0.0634(12) Uani 1 1 d . . . . .
H15 H 1.1912 0.6477 0.3850 0.076 Uiso 1 1 calc R U . . .
C16 C 1.1342(3) 0.4125(5) 0.37994(12) 0.0565(10) Uani 1 1 d . . . . .
H16 H 1.1705 0.3604 0.4022 0.068 Uiso 1 1 calc R U . . .
C17 C 1.0327(3) 0.0002(5) 0.41624(16) 0.0915(16) Uani 1 1 d . . . . .
H17A H 1.0478 0.0351 0.4449 0.137 Uiso 1 1 calc R U . . .
H17B H 1.0949 0.0244 0.3983 0.137 Uiso 1 1 calc R U . . .
H17C H 1.0197 -0.1137 0.4161 0.137 Uiso 1 1 calc R U . . .
N1 N 1.0316(2) 0.4599(3) 0.32687(9) 0.0439(8) Uani 1 1 d . . . . .
N2 N 1.0648(2) 0.3400(3) 0.35343(9) 0.0496(8) Uani 1 1 d . . . . .
N3 N 0.8450(3) 0.2514(3) 0.33854(10) 0.0451(8) Uani 1 1 d . . . . .
N4 N 0.7026(4) -0.1745(4) 0.50602(12) 0.0789(11) Uani 1 1 d . . . . .
O1 O 0.6585(2) 0.2601(3) 0.34112(9) 0.0699(8) Uani 1 1 d . . . . .
O2 O 0.93821(19) 0.0807(3) 0.40070(8) 0.0661(8) Uani 1 1 d . . . . .
O3 O 0.7846(3) -0.2228(4) 0.52421(11) 0.1064(12) Uani 1 1 d . . . . .
O4 O 0.6086(3) -0.2069(4) 0.51731(11) 0.1164(14) Uani 1 1 d . . . . .
H1N H 0.905(3) 0.225(4) 0.3507(11) 0.059(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(5) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 N1 1.427(4) . ?
C6 N3 1.422(4) . ?
C7 O1 1.221(4) . ?
C7 N3 1.351(4) . ?
C7 C8 1.506(5) . ?
C8 C13 1.391(4) . ?
C8 C9 1.394(4) . ?
C9 O2 1.354(4) . ?
C9 C10 1.382(5) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(5) . ?
C11 N4 1.475(5) . ?
C12 C13 1.373(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N1 1.352(4) . ?
C14 C15 1.357(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 N2 1.326(4) . ?
C16 H16 0.9300 . ?
C17 O2 1.411(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.359(3) . ?
N3 H1N 0.85(3) . ?
N4 O3 1.213(4) . ?
N4 O4 1.221(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(4) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 N1 117.5(3) . . ?
C6 C5 N1 121.7(3) . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 N3 121.5(3) . . ?
C5 C6 N3 120.4(3) . . ?
O1 C7 N3 122.8(3) . . ?
O1 C7 C8 119.2(3) . . ?
N3 C7 C8 118.0(3) . . ?
C13 C8 C9 117.6(3) . . ?
C13 C8 C7 115.3(3) . . ?
C9 C8 C7 127.1(3) . . ?
O2 C9 C10 122.0(3) . . ?
O2 C9 C8 117.6(3) . . ?
C10 C9 C8 120.4(3) . . ?
C11 C10 C9 118.8(4) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 123.1(4) . . ?
C12 C11 N4 118.3(4) . . ?
C10 C11 N4 118.6(4) . . ?
C11 C12 C13 116.8(4) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 H12 121.6 . . ?
C12 C13 C8 123.3(4) . . ?
C12 C13 H13 118.4 . . ?
C8 C13 H13 118.4 . . ?
N1 C14 C15 106.8(3) . . ?
N1 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
C14 C15 C16 105.3(3) . . ?
C14 C15 H15 127.4 . . ?
C16 C15 H15 127.4 . . ?
N2 C16 C15 112.4(3) . . ?
N2 C16 H16 123.8 . . ?
C15 C16 H16 123.8 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 N1 N2 111.7(3) . . ?
C14 N1 C5 126.7(3) . . ?
N2 N1 C5 121.6(3) . . ?
C16 N2 N1 103.8(3) . . ?
C7 N3 C6 125.2(3) . . ?
C7 N3 H1N 121(2) . . ?
C6 N3 H1N 114(2) . . ?
O3 N4 O4 123.6(4) . . ?
O3 N4 C11 118.3(4) . . ?
O4 N4 C11 118.2(4) . . ?
C9 O2 C17 120.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(5) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 2.0(5) . . . . ?
C3 C4 C5 N1 -174.8(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C1 C6 N3 -178.6(3) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
N1 C5 C6 C1 175.4(3) . . . . ?
C4 C5 C6 N3 177.1(3) . . . . ?
N1 C5 C6 N3 -6.3(5) . . . . ?
O1 C7 C8 C13 0.8(4) . . . . ?
N3 C7 C8 C13 -179.6(3) . . . . ?
O1 C7 C8 C9 179.8(3) . . . . ?
N3 C7 C8 C9 -0.5(5) . . . . ?
C13 C8 C9 O2 179.3(3) . . . . ?
C7 C8 C9 O2 0.3(5) . . . . ?
C13 C8 C9 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 -180.0(3) . . . . ?
O2 C9 C10 C11 -179.5(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C9 C10 C11 N4 179.7(3) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
N4 C11 C12 C13 180.0(3) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C9 C8 C13 C12 0.7(5) . . . . ?
C7 C8 C13 C12 179.8(3) . . . . ?
N1 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 N2 0.6(4) . . . . ?
C15 C14 N1 N2 0.2(4) . . . . ?
C15 C14 N1 C5 179.3(3) . . . . ?
C4 C5 N1 C14 39.9(4) . . . . ?
C6 C5 N1 C14 -136.8(3) . . . . ?
C4 C5 N1 N2 -141.0(3) . . . . ?
C6 C5 N1 N2 42.3(4) . . . . ?
C15 C16 N2 N1 -0.4(4) . . . . ?
C14 N1 N2 C16 0.1(3) . . . . ?
C5 N1 N2 C16 -179.1(3) . . . . ?
O1 C7 N3 C6 -5.2(5) . . . . ?
C8 C7 N3 C6 175.2(3) . . . . ?
C1 C6 N3 C7 -31.2(5) . . . . ?
C5 C6 N3 C7 150.6(3) . . . . ?
C12 C11 N4 O3 -178.1(4) . . . . ?
C10 C11 N4 O3 1.9(5) . . . . ?
C12 C11 N4 O4 3.6(5) . . . . ?
C10 C11 N4 O4 -176.5(4) . . . . ?
C10 C9 O2 C17 10.4(5) . . . . ?
C8 C9 O2 C17 -169.8(3) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_308
_database_code_depnum_ccdc_archive 'CCDC 1479826'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3 O2'
_chemical_formula_weight         395.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6084(10)
_cell_length_b                   11.1938(17)
_cell_length_c                   19.649(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2113.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2924
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      21.75

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13348
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         24.092
_diffrn_reflns_theta_full        24.092
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3328
_reflns_number_gt                2403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.5926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0178(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.9(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6499(6) 0.7832(5) 0.9589(3) 0.0920(16) Uani 1 1 d . . . . .
H1 H 0.6056 0.7137 0.9731 0.110 Uiso 1 1 calc R U . . .
C2 C 0.7091(8) 0.8599(6) 1.0054(3) 0.107(2) Uani 1 1 d . . . . .
H2 H 0.7041 0.8414 1.0515 0.129 Uiso 1 1 calc R U . . .
C3 C 0.7740(7) 0.9610(7) 0.9860(4) 0.115(2) Uani 1 1 d . . . . .
H3 H 0.8132 1.0108 1.0186 0.137 Uiso 1 1 calc R U . . .
C4 C 0.7825(6) 0.9904(6) 0.9199(5) 0.108(2) Uani 1 1 d . . . . .
H4 H 0.8281 1.0602 0.9072 0.129 Uiso 1 1 calc R U . . .
C5 C 0.7254(5) 0.9198(6) 0.8714(3) 0.0909(17) Uani 1 1 d . . . . .
H5 H 0.7308 0.9425 0.8259 0.109 Uiso 1 1 calc R U . . .
C6 C 0.6581(5) 0.8126(5) 0.8889(3) 0.0760(14) Uani 1 1 d . . . . .
C7 C 0.5978(5) 0.7372(6) 0.8359(3) 0.0930(17) Uani 1 1 d . . . . .
H7 H 0.5955 0.7708 0.7927 0.112 Uiso 1 1 calc R U . . .
C8 C 0.5492(5) 0.6349(5) 0.8403(3) 0.0879(17) Uani 1 1 d . . . . .
H8 H 0.5455 0.6009 0.8834 0.106 Uiso 1 1 calc R U . . .
C9 C 0.4936(5) 0.5580(4) 0.7798(2) 0.0746(13) Uani 1 1 d . . . . .
H9A H 0.4754 0.6085 0.7407 0.090 Uiso 1 1 calc R U . . .
H9B H 0.5623 0.4987 0.7670 0.090 Uiso 1 1 calc R U . . .
C10 C 0.2440(4) 0.5626(4) 0.8033(2) 0.0575(11) Uani 1 1 d . . . . .
C11 C 0.2323(5) 0.6783(4) 0.7810(2) 0.0707(13) Uani 1 1 d . . . . .
H11 H 0.3105 0.7181 0.7647 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1064(5) 0.7356(5) 0.7827(2) 0.0819(14) Uani 1 1 d . . . . .
H12 H 0.0993 0.8134 0.7664 0.098 Uiso 1 1 calc R U . . .
C13 C -0.0069(6) 0.6806(5) 0.8075(3) 0.0909(16) Uani 1 1 d . . . . .
H13 H -0.0917 0.7205 0.8092 0.109 Uiso 1 1 calc R U . . .
C14 C 0.0030(5) 0.5649(5) 0.8306(2) 0.0788(14) Uani 1 1 d . . . . .
H14 H -0.0759 0.5277 0.8480 0.095 Uiso 1 1 calc R U . . .
C15 C 0.1274(4) 0.5020(4) 0.8286(2) 0.0557(10) Uani 1 1 d . . . . .
C16 C 0.1210(4) 0.3759(4) 0.8535(2) 0.0609(11) Uani 1 1 d . . . . .
C17 C 0.2517(4) 0.1892(4) 0.8716(2) 0.0572(11) Uani 1 1 d . . . . .
C18 C 0.1433(5) 0.1071(4) 0.8656(3) 0.0782(14) Uani 1 1 d . . . . .
H18 H 0.0584 0.1307 0.8472 0.094 Uiso 1 1 calc R U . . .
C19 C 0.1621(6) -0.0088(5) 0.8867(3) 0.0969(18) Uani 1 1 d . . . . .
H19 H 0.0895 -0.0633 0.8825 0.116 Uiso 1 1 calc R U . . .
C20 C 0.2863(6) -0.0450(5) 0.9138(3) 0.103(2) Uani 1 1 d . . . . .
H20 H 0.2973 -0.1236 0.9281 0.123 Uiso 1 1 calc R U . . .
C21 C 0.3940(5) 0.0338(4) 0.9199(3) 0.0792(15) Uani 1 1 d . . . . .
H21 H 0.4785 0.0089 0.9381 0.095 Uiso 1 1 calc R U . . .
C22 C 0.3768(4) 0.1502(4) 0.8990(2) 0.0576(11) Uani 1 1 d . . . . .
C23 C 0.5557(5) 0.2625(5) 0.9637(3) 0.0811(15) Uani 1 1 d . . . . .
H23 H 0.5303 0.2409 1.0077 0.097 Uiso 1 1 calc R U . . .
C24 C 0.6657(5) 0.3318(5) 0.9465(3) 0.0887(16) Uani 1 1 d . . . . .
H24 H 0.7296 0.3677 0.9757 0.106 Uiso 1 1 calc R U . . .
N1 N 0.2388(4) 0.3089(3) 0.85041(19) 0.0598(10) Uani 1 1 d . . . . .
N2 N 0.4902(3) 0.2305(3) 0.90706(17) 0.0538(8) Uani 1 1 d . . . . .
N3 N 0.5536(4) 0.2765(4) 0.85163(19) 0.0762(12) Uani 1 1 d . . . . .
N4 N 0.6623(5) 0.3377(5) 0.8767(3) 0.1090(16) Uani 1 1 d . . . . .
O1 O 0.3670(3) 0.5001(2) 0.80136(15) 0.0676(8) Uani 1 1 d . . . . .
O2 O 0.0117(3) 0.3352(3) 0.87566(17) 0.0866(10) Uani 1 1 d . . . . .
H1N H 0.312(4) 0.351(4) 0.840(2) 0.066(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(8) . ?
C1 C6 1.416(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.343(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(7) . ?
C7 C8 1.240(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.561(7) . ?
C8 H8 0.9300 . ?
C9 O1 1.441(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.371(6) . ?
C10 O1 1.375(5) . ?
C10 C15 1.401(6) . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.343(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.496(6) . ?
C16 O2 1.224(5) . ?
C16 N1 1.359(5) . ?
C17 C22 1.387(6) . ?
C17 C18 1.394(6) . ?
C17 N1 1.409(5) . ?
C18 C19 1.374(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(6) . ?
C21 H21 0.9300 . ?
C22 N2 1.422(5) . ?
C23 N2 1.328(5) . ?
C23 C24 1.354(7) . ?
C23 H23 0.9300 . ?
C24 N4 1.375(7) . ?
C24 H24 0.9300 . ?
N1 H1N 0.87(4) . ?
N2 N3 1.350(5) . ?
N3 N4 1.343(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.5(6) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C3 C2 C1 121.8(6) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 120.6(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 117.5(5) . . ?
C5 C6 C7 120.1(6) . . ?
C1 C6 C7 122.4(6) . . ?
C8 C7 C6 129.4(6) . . ?
C8 C7 H7 115.3 . . ?
C6 C7 H7 115.3 . . ?
C7 C8 C9 125.9(6) . . ?
C7 C8 H8 117.1 . . ?
C9 C8 H8 117.1 . . ?
O1 C9 C8 108.3(4) . . ?
O1 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C11 C10 O1 122.9(4) . . ?
C11 C10 C15 120.3(4) . . ?
O1 C10 C15 116.8(4) . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 121.9(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 117.0(4) . . ?
C14 C15 C16 115.8(4) . . ?
C10 C15 C16 127.3(4) . . ?
O2 C16 N1 121.7(4) . . ?
O2 C16 C15 120.1(4) . . ?
N1 C16 C15 118.1(4) . . ?
C22 C17 C18 118.2(4) . . ?
C22 C17 N1 119.4(4) . . ?
C18 C17 N1 122.4(4) . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.7(5) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.6(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C17 121.2(4) . . ?
C21 C22 N2 118.2(4) . . ?
C17 C22 N2 120.5(4) . . ?
N2 C23 C24 108.4(4) . . ?
N2 C23 H23 125.8 . . ?
C24 C23 H23 125.8 . . ?
C23 C24 N4 104.9(4) . . ?
C23 C24 H24 127.5 . . ?
N4 C24 H24 127.5 . . ?
C16 N1 C17 125.7(4) . . ?
C16 N1 H1N 113(3) . . ?
C17 N1 H1N 121(3) . . ?
C23 N2 N3 111.1(4) . . ?
C23 N2 C22 128.8(4) . . ?
N3 N2 C22 119.8(3) . . ?
N4 N3 N2 104.5(4) . . ?
N3 N4 C24 111.1(5) . . ?
C10 O1 C9 120.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(9) . . . . ?
C1 C2 C3 C4 0.2(10) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C3 C4 C5 C6 -1.2(8) . . . . ?
C4 C5 C6 C1 1.3(7) . . . . ?
C4 C5 C6 C7 -179.7(5) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C2 C1 C6 C7 -179.6(5) . . . . ?
C5 C6 C7 C8 170.9(5) . . . . ?
C1 C6 C7 C8 -10.1(8) . . . . ?
C6 C7 C8 C9 -176.6(4) . . . . ?
C7 C8 C9 O1 -137.8(5) . . . . ?
O1 C10 C11 C12 178.5(4) . . . . ?
C15 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C13 1.6(7) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
C12 C13 C14 C15 -0.4(8) . . . . ?
C13 C14 C15 C10 1.3(7) . . . . ?
C13 C14 C15 C16 -178.2(4) . . . . ?
C11 C10 C15 C14 -0.7(6) . . . . ?
O1 C10 C15 C14 -180.0(4) . . . . ?
C11 C10 C15 C16 178.7(4) . . . . ?
O1 C10 C15 C16 -0.5(6) . . . . ?
C14 C15 C16 O2 -2.0(6) . . . . ?
C10 C15 C16 O2 178.6(4) . . . . ?
C14 C15 C16 N1 177.7(4) . . . . ?
C10 C15 C16 N1 -1.8(6) . . . . ?
C22 C17 C18 C19 0.3(7) . . . . ?
N1 C17 C18 C19 179.5(5) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C18 C19 C20 C21 -0.4(9) . . . . ?
C19 C20 C21 C22 0.4(8) . . . . ?
C20 C21 C22 C17 0.0(7) . . . . ?
C20 C21 C22 N2 179.0(4) . . . . ?
C18 C17 C22 C21 -0.3(6) . . . . ?
N1 C17 C22 C21 -179.6(4) . . . . ?
C18 C17 C22 N2 -179.3(4) . . . . ?
N1 C17 C22 N2 1.5(6) . . . . ?
N2 C23 C24 N4 -0.7(6) . . . . ?
O2 C16 N1 C17 -0.5(7) . . . . ?
C15 C16 N1 C17 179.9(4) . . . . ?
C22 C17 N1 C16 -146.8(4) . . . . ?
C18 C17 N1 C16 34.0(7) . . . . ?
C24 C23 N2 N3 0.1(5) . . . . ?
C24 C23 N2 C22 174.2(4) . . . . ?
C21 C22 N2 C23 -59.4(6) . . . . ?
C17 C22 N2 C23 119.6(5) . . . . ?
C21 C22 N2 N3 114.2(5) . . . . ?
C17 C22 N2 N3 -66.8(5) . . . . ?
C23 N2 N3 N4 0.6(5) . . . . ?
C22 N2 N3 N4 -174.1(4) . . . . ?
N2 N3 N4 C24 -1.0(6) . . . . ?
C23 C24 N4 N3 1.1(6) . . . . ?
C11 C10 O1 C9 4.5(6) . . . . ?
C15 C10 O1 C9 -176.3(4) . . . . ?
C8 C9 O1 C10 78.4(5) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.030

