# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_IC5
_database_code_depnum_ccdc_archive 'CCDC 1551965'
_audit_update_record             
;
2017-07-28 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'ethyl 6-methoxy-4-(phenylselanyl)quinoline-2-carboxylate '
_chemical_name_common            ?
_chemical_melting_point          391-396
_chemical_formula_moiety         'C19 H17 N O3 Se'
_chemical_formula_sum            'C19 H17 N O3 Se'
_chemical_formula_weight         386.29

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1372(5)
_cell_length_b                   10.2407(4)
_cell_length_c                   10.3976(5)
_cell_angle_alpha                69.466(2)
_cell_angle_beta                 80.191(2)
_cell_angle_gamma                70.859(2)
_cell_volume                     859.05(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.44

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   0.5584
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.289
_exptl_absorpt_coefficient_mu    2.202
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            12521
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         26.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3555
_reflns_number_gt                3017
_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-2014/6 (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)+(0.0310P)²+0.4949P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.6945(3) 0.5455(2) 0.7487(2) 0.0459(5) Uani 1 1 d . . . . .
C2 C 0.8476(3) 0.4686(3) 0.7703(3) 0.0633(7) Uani 1 1 d . . . . .
H2 H 0.8957 0.4726 0.8402 0.076 Uiso 1 1 calc R U . . .
C3 C 0.9302(3) 0.3848(3) 0.6871(3) 0.0721(8) Uani 1 1 d . . . . .
H3 H 1.0344 0.3342 0.7005 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8609(3) 0.3761(3) 0.5869(3) 0.0617(7) Uani 1 1 d . . . . .
H4 H 0.9167 0.3189 0.5323 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7091(4) 0.4512(3) 0.5662(3) 0.0675(7) Uani 1 1 d . . . . .
H5 H 0.6611 0.4441 0.4979 0.081 Uiso 1 1 calc R U . . .
C6 C 0.6254(3) 0.5382(3) 0.6454(3) 0.0610(7) Uani 1 1 d . . . . .
H6 H 0.5225 0.5915 0.6287 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5777(3) 0.8466(2) 0.7558(2) 0.0409(5) Uani 1 1 d . . . . .
C8 C 0.4764(2) 0.9650(2) 0.7983(2) 0.0381(4) Uani 1 1 d . . . . .
C9 C 0.4870(2) 1.1062(2) 0.7196(2) 0.0411(5) Uani 1 1 d . . . . .
C10 C 0.6714(2) 1.0204(2) 0.5685(2) 0.0420(5) Uani 1 1 d . . . . .
C11 C 0.6733(3) 0.8759(2) 0.6394(2) 0.0445(5) Uani 1 1 d . . . . .
H11 H 0.7387 0.8007 0.6079 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7822(3) 1.0461(2) 0.4442(2) 0.0486(5) Uani 1 1 d . . . . .
C13 C 0.8749(3) 1.2159(3) 0.2586(3) 0.0652(7) Uani 1 1 d . . . . .
H13A H 0.8585 1.1769 0.1914 0.078 Uiso 1 1 calc R U . . .
H13B H 0.9816 1.1706 0.2840 0.078 Uiso 1 1 calc R U . . .
C14 C 0.8441(4) 1.3753(4) 0.1998(3) 0.0842(10) Uani 1 1 d . . . . .
H14A H 0.9126 1.3978 0.1196 0.126 Uiso 1 1 calc R U . . .
H14B H 0.8613 1.4128 0.2668 0.126 Uiso 1 1 calc R U . . .
H14C H 0.7385 1.4191 0.1747 0.126 Uiso 1 1 calc R U . . .
C15 C 0.3927(3) 1.2257(2) 0.7634(2) 0.0528(6) Uani 1 1 d . . . . .
H15 H 0.3994 1.3190 0.7139 0.063 Uiso 1 1 calc R U . . .
C16 C 0.2929(3) 1.2059(3) 0.8763(3) 0.0527(6) Uani 1 1 d . . . . .
H16 H 0.2330 1.2854 0.9041 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2795(3) 1.0660(2) 0.9516(2) 0.0450(5) Uani 1 1 d . . . . .
C18 C 0.1522(3) 0.9224(3) 1.1385(3) 0.0642(7) Uani 1 1 d . . . . .
H18A H 0.0743 0.9326 1.2119 0.096 Uiso 1 1 calc R U . . .
H18B H 0.2485 0.8575 1.1763 0.096 Uiso 1 1 calc R U . . .
H18C H 0.1202 0.8834 1.0801 0.096 Uiso 1 1 calc R U . . .
C19 C 0.3701(3) 0.9475(2) 0.9150(2) 0.0427(5) Uani 1 1 d . . . . .
H19 H 0.3621 0.8551 0.9667 0.051 Uiso 1 1 calc R U . . .
N1 N 0.5834(2) 1.13405(19) 0.60495(18) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.7694(2) 1.18545(17) 0.37939(17) 0.0561(4) Uani 1 1 d . . . . .
O2 O 0.8732(3) 0.9491(2) 0.4084(2) 0.0836(7) Uani 1 1 d . . . . .
O3 O 0.1725(2) 1.06182(19) 1.05990(17) 0.0598(5) Uani 1 1 d . . . . .
Se Se 0.57551(4) 0.65420(2) 0.86764(3) 0.06370(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.370(4) . ?
C1 C2 1.374(4) . ?
C1 Se 1.914(2) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.369(3) . ?
C7 C8 1.422(3) . ?
C7 Se 1.910(2) . ?
C8 C9 1.415(3) . ?
C8 C19 1.416(3) . ?
C9 N1 1.359(3) . ?
C9 C15 1.419(3) . ?
C10 N1 1.318(3) . ?
C10 C11 1.398(3) . ?
C10 C12 1.502(3) . ?
C11 H11 0.9300 . ?
C12 O2 1.196(3) . ?
C12 O1 1.321(3) . ?
C13 O1 1.454(3) . ?
C13 C14 1.475(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.356(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(3) . ?
C16 H16 0.9300 . ?
C17 O3 1.358(2) . ?
C17 C19 1.364(3) . ?
C18 O3 1.430(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.4(2) . . ?
C6 C1 Se 120.07(19) . . ?
C2 C1 Se 120.41(19) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C11 C7 C8 118.73(19) . . ?
C11 C7 Se 123.58(16) . . ?
C8 C7 Se 117.67(15) . . ?
C9 C8 C19 119.57(18) . . ?
C9 C8 C7 116.98(18) . . ?
C19 C8 C7 123.44(19) . . ?
N1 C9 C8 123.82(18) . . ?
N1 C9 C15 117.89(19) . . ?
C8 C9 C15 118.28(19) . . ?
N1 C10 C11 124.94(19) . . ?
N1 C10 C12 118.03(19) . . ?
C11 C10 C12 116.99(18) . . ?
C7 C11 C10 119.08(19) . . ?
C7 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
O2 C12 O1 123.7(2) . . ?
O2 C12 C10 122.8(2) . . ?
O1 C12 C10 113.56(18) . . ?
O1 C13 C14 108.1(2) . . ?
O1 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O1 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C9 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C9 C15 H15 119.5 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
O3 C17 C19 124.9(2) . . ?
O3 C17 C16 114.53(19) . . ?
C19 C17 C16 120.58(19) . . ?
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 . . ?
C17 C19 C8 120.1(2) . . ?
C17 C19 H19 120.0 . . ?
C8 C19 H19 120.0 . . ?
C10 N1 C9 116.38(18) . . ?
C12 O1 C13 115.57(18) . . ?
C17 O3 C18 116.80(18) . . ?
C7 Se C1 100.38(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(4) . . . . ?
Se C1 C2 C3 177.0(2) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
Se C1 C6 C5 -175.5(2) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C11 C7 C8 C9 -2.9(3) . . . . ?
Se C7 C8 C9 175.80(16) . . . . ?
C11 C7 C8 C19 178.4(2) . . . . ?
Se C7 C8 C19 -2.9(3) . . . . ?
C19 C8 C9 N1 -178.9(2) . . . . ?
C7 C8 C9 N1 2.4(3) . . . . ?
C19 C8 C9 C15 1.8(3) . . . . ?
C7 C8 C9 C15 -177.0(2) . . . . ?
C8 C7 C11 C10 1.8(3) . . . . ?
Se C7 C11 C10 -176.85(17) . . . . ?
N1 C10 C11 C7 0.1(4) . . . . ?
C12 C10 C11 C7 178.0(2) . . . . ?
N1 C10 C12 O2 175.2(3) . . . . ?
C11 C10 C12 O2 -2.8(4) . . . . ?
N1 C10 C12 O1 -4.6(3) . . . . ?
C11 C10 C12 O1 177.4(2) . . . . ?
N1 C9 C15 C16 179.4(2) . . . . ?
C8 C9 C15 C16 -1.1(4) . . . . ?
C9 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 O3 -178.3(2) . . . . ?
C15 C16 C17 C19 2.1(4) . . . . ?
O3 C17 C19 C8 178.9(2) . . . . ?
C16 C17 C19 C8 -1.5(4) . . . . ?
C9 C8 C19 C17 -0.5(3) . . . . ?
C7 C8 C19 C17 178.2(2) . . . . ?
C11 C10 N1 C9 -0.8(3) . . . . ?
C12 C10 N1 C9 -178.6(2) . . . . ?
C8 C9 N1 C10 -0.6(3) . . . . ?
C15 C9 N1 C10 178.8(2) . . . . ?
O2 C12 O1 C13 -0.1(4) . . . . ?
C10 C12 O1 C13 179.8(2) . . . . ?
C14 C13 O1 C12 179.9(3) . . . . ?
C19 C17 O3 C18 -1.5(4) . . . . ?
C16 C17 O3 C18 178.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18A O2 0.96 2.52 3.477(3) 177.8 1_456
C18 H18A O2 0.96 2.52 3.477(3) 177.8 1_456

_refine_diff_density_max         0.755
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_JZS8
_database_code_depnum_ccdc_archive 'CCDC 1551966'
_audit_update_record             
;
2017-07-28 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'Ethyl 4-(3-hydroxy-3-methylbut-1-yn-1-yl)-6-methoxyquinoline-2-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          411-414
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2169(5)
_cell_length_b                   9.1554(5)
_cell_length_c                   11.7431(7)
_cell_angle_alpha                94.646(2)
_cell_angle_beta                 108.461(2)
_cell_angle_gamma                96.454(2)
_cell_volume                     826.25(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.36
_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            23410
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3378
_reflns_number_gt                2982
_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    SIR2014
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0608P)²+0.2022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3378
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O3 O -0.12814(15) 0.23580(12) -0.24860(10) 0.0604(3) Uani 1 1 d . . . . .
O1 O 0.63045(16) 0.69600(11) 0.39721(9) 0.0572(3) Uani 1 1 d . . . . .
O2 O 0.63280(19) 0.45673(13) 0.42008(10) 0.0742(4) Uani 1 1 d . . . . .
O4 O 0.24497(19) 0.80448(13) -0.33812(10) 0.0696(4) Uani 1 1 d . . . . .
H1O4 H 0.3083 0.7405 -0.3491 0.104 Uiso 1 1 d R U . . .
N1 N 0.34381(15) 0.40212(12) 0.20879(10) 0.0396(3) Uani 1 1 d . . . . .
C1 C -0.1345(3) 0.3159(2) -0.34844(15) 0.0747(5) Uani 1 1 d . . . . .
H1B H -0.1546 0.4150 -0.3301 0.112 Uiso 1 1 calc R U . . .
H1C H -0.2268 0.2676 -0.4188 0.112 Uiso 1 1 calc R U . . .
H1A H -0.0262 0.3190 -0.3639 0.112 Uiso 1 1 calc R U . . .
C2 C -0.00792(17) 0.29027(15) -0.13972(12) 0.0418(3) Uani 1 1 d . . . . .
C3 C -0.01034(18) 0.20290(15) -0.04595(14) 0.0457(3) Uani 1 1 d . . . . .
H3 H -0.0916 0.1180 -0.0622 0.055 Uiso 1 1 calc R U . . .
C4 C 0.10433(18) 0.24165(15) 0.06691(13) 0.0429(3) Uani 1 1 d . . . . .
H4 H 0.1014 0.1827 0.1273 0.052 Uiso 1 1 calc R U . . .
C5 C 0.22919(16) 0.37118(13) 0.09452(11) 0.0351(3) Uani 1 1 d . . . . .
C6 C 0.45563(18) 0.52505(14) 0.23356(11) 0.0392(3) Uani 1 1 d . . . . .
C7 C 0.5823(2) 0.55300(16) 0.36010(12) 0.0470(3) Uani 1 1 d . . . . .
C8 C 0.7468(3) 0.73915(19) 0.52182(14) 0.0646(5) Uani 1 1 d . . . . .
H8A H 0.8615 0.7146 0.5301 0.078 Uiso 1 1 calc R U . . .
H8B H 0.7027 0.6876 0.5774 0.078 Uiso 1 1 calc R U . . .
C9 C 0.7547(4) 0.9001(2) 0.54830(18) 0.0905(7) Uani 1 1 d . . . . .
H9B H 0.8056 0.9500 0.4963 0.136 Uiso 1 1 calc R U . . .
H9A H 0.8239 0.9317 0.6312 0.136 Uiso 1 1 calc R U . . .
H9C H 0.6396 0.9235 0.5347 0.136 Uiso 1 1 calc R U . . .
C10 C 0.10783(17) 0.41802(14) -0.11676(12) 0.0384(3) Uani 1 1 d . . . . .
H10 H 0.1076 0.4759 -0.1783 0.046 Uiso 1 1 calc R U . . .
C11 C 0.22737(16) 0.46108(13) 0.00103(11) 0.0330(3) Uani 1 1 d . . . . .
C12 C 0.34917(16) 0.59392(13) 0.03297(11) 0.0347(3) Uani 1 1 d . . . . .
C13 C 0.46162(18) 0.62492(13) 0.14976(12) 0.0391(3) Uani 1 1 d . . . . .
H13 H 0.5411 0.7115 0.1731 0.047 Uiso 1 1 calc R U . . .
C14 C 0.35139(17) 0.69321(14) -0.05502(11) 0.0383(3) Uani 1 1 d . . . . .
C15 C 0.34659(17) 0.77626(14) -0.12893(12) 0.0396(3) Uani 1 1 d . . . . .
C16 C 0.33583(18) 0.88085(14) -0.22037(11) 0.0407(3) Uani 1 1 d . . . . .
C17 C 0.2273(2) 0.99829(17) -0.20037(16) 0.0554(4) Uani 1 1 d . . . . .
H17B H 0.2173 1.0646 -0.2607 0.083 Uiso 1 1 calc R U . . .
H17A H 0.2823 1.0530 -0.1215 0.083 Uiso 1 1 calc R U . . .
H17C H 0.1140 0.9514 -0.2062 0.083 Uiso 1 1 calc R U . . .
C18 C 0.5158(2) 0.95219(18) -0.21137(17) 0.0588(4) Uani 1 1 d . . . . .
H18A H 0.5814 0.8770 -0.2268 0.088 Uiso 1 1 calc R U . . .
H18B H 0.5733 1.0039 -0.1316 0.088 Uiso 1 1 calc R U . . .
H18C H 0.5069 1.0208 -0.2699 0.088 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.3584(17) . ?
O3 C1 1.423(2) . ?
O1 C7 1.3200(17) . ?
O1 C8 1.4652(17) . ?
O2 C7 1.2011(17) . ?
O4 C16 1.4250(16) . ?
O4 H1O4 0.8542 . ?
N1 C6 1.3193(17) . ?
N1 C5 1.3586(17) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1A 0.9600 . ?
C2 C10 1.3718(19) . ?
C2 C3 1.416(2) . ?
C3 C4 1.352(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.4205(18) . ?
C4 H4 0.9300 . ?
C5 C11 1.4219(16) . ?
C6 C13 1.4047(17) . ?
C6 C7 1.5021(19) . ?
C8 C9 1.471(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.4133(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.4270(17) . ?
C12 C13 1.3751(18) . ?
C12 C14 1.4334(16) . ?
C13 H13 0.9300 . ?
C14 C15 1.1937(18) . ?
C15 C16 1.4843(17) . ?
C16 C18 1.516(2) . ?
C16 C17 1.521(2) . ?
C17 H17B 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O3 C1 117.89(13) . . ?
C7 O1 C8 117.41(12) . . ?
C16 O4 H1O4 105.0 . . ?
C6 N1 C5 117.22(11) . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
O3 C2 C10 125.53(13) . . ?
O3 C2 C3 113.96(12) . . ?
C10 C2 C3 120.51(12) . . ?
C4 C3 C2 120.66(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.92(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 118.14(11) . . ?
N1 C5 C11 123.68(11) . . ?
C4 C5 C11 118.18(12) . . ?
N1 C6 C13 124.04(12) . . ?
N1 C6 C7 115.37(11) . . ?
C13 C6 C7 120.59(12) . . ?
O2 C7 O1 124.32(13) . . ?
O2 C7 C6 123.97(13) . . ?
O1 C7 C6 111.70(11) . . ?
O1 C8 C9 106.97(14) . . ?
O1 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O1 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
C2 C10 C11 119.57(12) . . ?
C2 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C5 120.11(11) . . ?
C10 C11 C12 123.03(11) . . ?
C5 C11 C12 116.85(11) . . ?
C13 C12 C11 118.56(11) . . ?
C13 C12 C14 121.17(11) . . ?
C11 C12 C14 120.27(11) . . ?
C12 C13 C6 119.58(11) . . ?
C12 C13 H13 120.2 . . ?
C6 C13 H13 120.2 . . ?
C15 C14 C12 177.44(14) . . ?
C14 C15 C16 178.29(14) . . ?
O4 C16 C15 109.57(11) . . ?
O4 C16 C18 111.29(12) . . ?
C15 C16 C18 110.36(12) . . ?
O4 C16 C17 105.85(12) . . ?
C15 C16 C17 109.18(11) . . ?
C18 C16 C17 110.48(12) . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O3 C2 C10 0.9(2) . . . . ?
C1 O3 C2 C3 -179.58(14) . . . . ?
O3 C2 C3 C4 178.63(12) . . . . ?
C10 C2 C3 C4 -1.8(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C6 N1 C5 C4 -178.16(12) . . . . ?
C6 N1 C5 C11 1.92(19) . . . . ?
C3 C4 C5 N1 -178.31(12) . . . . ?
C3 C4 C5 C11 1.6(2) . . . . ?
C5 N1 C6 C13 0.6(2) . . . . ?
C5 N1 C6 C7 -178.69(11) . . . . ?
C8 O1 C7 O2 -3.0(2) . . . . ?
C8 O1 C7 C6 176.74(13) . . . . ?
N1 C6 C7 O2 29.5(2) . . . . ?
C13 C6 C7 O2 -149.77(16) . . . . ?
N1 C6 C7 O1 -150.19(13) . . . . ?
C13 C6 C7 O1 30.53(19) . . . . ?
C7 O1 C8 C9 -169.59(18) . . . . ?
O3 C2 C10 C11 -179.41(12) . . . . ?
C3 C2 C10 C11 1.1(2) . . . . ?
C2 C10 C11 C5 0.97(18) . . . . ?
C2 C10 C11 C12 -178.53(11) . . . . ?
N1 C5 C11 C10 177.62(11) . . . . ?
C4 C5 C11 C10 -2.30(18) . . . . ?
N1 C5 C11 C12 -2.86(18) . . . . ?
C4 C5 C11 C12 177.23(11) . . . . ?
C10 C11 C12 C13 -179.16(11) . . . . ?
C5 C11 C12 C13 1.33(17) . . . . ?
C10 C11 C12 C14 1.76(18) . . . . ?
C5 C11 C12 C14 -177.75(11) . . . . ?
C11 C12 C13 C6 0.89(18) . . . . ?
C14 C12 C13 C6 179.96(12) . . . . ?
N1 C6 C13 C12 -2.0(2) . . . . ?
C7 C6 C13 C12 177.24(12) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036

_shelxl_version_number           2014/6

