# 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_NITK366_a_a
_database_code_depnum_ccdc_archive 'CCDC 1423053'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Diethyl 6-amino-4-(benzofuran-2-yl)-5-cyano-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate '
_chemical_name_common            ?
_chemical_melting_point          182-183C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N3 O5'
_chemical_formula_weight         456.46

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.4240(6)
_cell_length_b                   21.2481(11)
_cell_length_c                   11.2337(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.875(2)
_cell_angle_gamma                90
_cell_volume                     2340.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17287
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         14.997
_diffrn_reflns_theta_full        14.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             945
_reflns_number_gt                908
_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)+(0.0339P)²+3.1962P] 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         945
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.067
_refine_ls_shift/su_mean         0.015

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
O001 O 0.3177(5) 0.51678(14) 0.3321(3) 0.0578(12) Uani 1 1 d . . . . .
O002 O 0.1134(4) 0.46834(18) 0.2696(3) 0.0648(14) Uani 1 1 d . . . . .
O003 O 0.3444(10) 0.6474(3) 0.6797(5) 0.0654(13) Uani 1 1 d . . . . .
N1 N 0.1020(7) 0.6081(5) 0.3682(9) 0.0410(15) Uani 1 1 d . . . . .
O1 O 0.2916(5) 0.4418(3) 0.5384(4) 0.0703(15) Uani 1 1 d . . . . .
O006 O 0.2225(4) 0.4580(2) 0.7025(4) 0.0766(17) Uani 1 1 d . . . . .
N007 N -0.0249(4) 0.6977(2) 0.3694(4) 0.0591(15) Uani 1 1 d . . . . .
H21 H -0.0658 0.7230 0.4044 0.071 Uiso 1 1 calc R U . . .
H22 H -0.0271 0.7045 0.2933 0.071 Uiso 1 1 calc R U . . .
C1 C 0.1581(7) 0.5511(6) 0.4228(14) 0.0370(18) Uani 1 1 d . . . . .
C009 C 0.0496(6) 0.6342(4) 0.5555(12) 0.040(2) Uani 1 1 d . . . . .
C00A C 0.0428(6) 0.6473(4) 0.4340(13) 0.0396(17) Uani 1 1 d . . . . .
C00B C 0.1403(9) 0.5828(5) 0.6295(8) 0.0367(15) Uani 1 1 d . . . . .
H00B H 0.0897 0.5601 0.6755 0.044 Uiso 1 1 calc R U . . .
C00C C 0.1742(6) 0.5360(5) 0.5437(14) 0.0355(18) Uani 1 1 d . . . . .
C00D C 0.1923(8) 0.5062(4) 0.3326(7) 0.0453(17) Uani 1 1 d . . . . .
C00E C 0.1019(15) 0.6253(5) 0.2439(14) 0.0431(18) Uani 1 1 d . . . . .
C00F C 0.2679(9) 0.6076(4) 0.7255(14) 0.0413(16) Uani 1 1 d . . . . .
C00G C 0.2287(7) 0.4756(5) 0.6019(8) 0.0478(18) Uani 1 1 d . . . . .
C00H C -0.0162(6) 0.6754(3) 0.6156(6) 0.0471(19) Uani 1 1 d . . . . .
N00I N -0.0673(5) 0.7088(3) 0.6637(5) 0.0734(17) Uani 1 1 d . . . . .
C00J C 0.3262(14) 0.5992(3) 0.8490(14) 0.061(2) Uani 1 1 d . . . . .
H24 H 0.2921 0.5742 0.8993 0.073 Uiso 1 1 calc R U . . .
C00K C 0.0050(12) 0.6022(3) 0.1399(19) 0.065(2) Uani 1 1 d . . . . .
H17 H -0.0626 0.5757 0.1479 0.078 Uiso 1 1 calc R U . . .
C00L C 0.4561(12) 0.6625(5) 0.787(2) 0.073(3) Uani 1 1 d . . . . .
C00M C 0.2005(12) 0.6658(6) 0.2323(12) 0.063(2) Uani 1 1 d . . . . .
C00N C 0.4480(15) 0.6343(6) 0.8921(14) 0.074(3) Uani 1 1 d . . . . .
C00O C 0.3645(5) 0.4770(2) 0.2497(6) 0.0776(18) Uani 1 1 d . . . . .
H12 H 0.3217 0.4360 0.2423 0.093 Uiso 1 1 calc R U . . .
H29 H 0.4624 0.4712 0.2868 0.093 Uiso 1 1 calc R U . . .
C00P C 0.0072(13) 0.6184(6) 0.0212(17) 0.089(3) Uani 1 1 d . . . . .
C00Q C 0.105(2) 0.6582(7) 0.0092(14) 0.102(4) Uani 1 1 d . . . . .
C00R C 0.2000(13) 0.6818(4) 0.113(2) 0.091(3) Uani 1 1 d . . . . .
C00S C 0.3535(8) 0.3827(3) 0.5910(5) 0.093(2) Uani 1 1 d . . . . .
H10 H 0.4124 0.3887 0.6780 0.111 Uiso 1 1 calc R U . . .
H11 H 0.2834 0.3525 0.5899 0.111 Uiso 1 1 calc R U . . .
C00T C 0.6661(17) 0.7099(5) 0.9022(18) 0.139(5) Uani 1 1 d . . . . .
C00U C 0.3316(6) 0.5051(3) 0.1232(6) 0.112(2) Uani 1 1 d . . . . .
H14 H 0.2344 0.5079 0.0839 0.167 Uiso 1 1 calc R U . . .
H13 H 0.3682 0.4792 0.0724 0.167 Uiso 1 1 calc R U . . .
H15 H 0.3707 0.5464 0.1308 0.167 Uiso 1 1 calc R U . . .
C00V C 0.5598(18) 0.7022(5) 0.7807(13) 0.123(3) Uani 1 1 d . . . . .
C00W C 0.4314(6) 0.3599(3) 0.5167(7) 0.134(2) Uani 1 1 d . . . . .
H8 H 0.3711 0.3496 0.4332 0.202 Uiso 1 1 calc R U . . .
H7 H 0.4809 0.3229 0.5558 0.202 Uiso 1 1 calc R U . . .
H9 H 0.4945 0.3918 0.5113 0.202 Uiso 1 1 calc R U . . .
C00X C 0.5573(17) 0.6450(5) 1.0081(9) 0.117(3) Uani 1 1 d . . . . .
H25 H 0.5586 0.6267 1.0837 0.140 Uiso 1 1 calc R U . . .
C00Y C 0.6597(13) 0.6835(6) 1.0021(14) 0.149(6) Uani 1 1 d . . . . .
H26 H 0.7309 0.6912 1.0773 0.179 Uiso 1 1 calc R U . . .
H28 H 0.541(4) 0.7135(18) 0.680(4) 0.06(2) Uiso 1 1 d . . . . .
H18 H 0.100(5) 0.669(2) -0.076(6) 0.12(3) Uiso 1 1 d . . . . .
H20 H 0.268(5) 0.681(2) 0.314(5) 0.07(3) Uiso 1 1 d . . . . .
H16 H -0.061(4) 0.6012(18) -0.046(5) 0.05(2) Uiso 1 1 d . . . . .
H27 H 0.700(5) 0.730(2) 0.828(5) 0.10(2) Uiso 1 1 d . . . . .
H19 H 0.269(5) 0.707(2) 0.104(6) 0.11(3) 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
O001 C00D 1.327(6) . ?
O001 C00O 1.455(5) . ?
O002 C00D 1.195(7) . ?
O003 C00F 1.376(6) . ?
O003 C00L 1.397(11) . ?
N1 C00A 1.390(7) . ?
N1 C1 1.393(8) . ?
N1 C00E 1.443(9) . ?
O1 C00G 1.331(7) . ?
O1 C00S 1.442(6) . ?
O006 C00G 1.213(7) . ?
N007 C00A 1.350(7) . ?
N007 H21 0.8600 . ?
N007 H22 0.8600 . ?
C1 C00C 1.349(7) . ?
C1 C00D 1.521(10) . ?
C009 C00A 1.370(8) . ?
C009 C00H 1.417(8) . ?
C009 C00B 1.499(8) . ?
C00B C00F 1.495(8) . ?
C00B C00C 1.508(8) . ?
C00B H00B 0.9800 . ?
C00C C00G 1.464(9) . ?
C00E C00K 1.351(8) . ?
C00E C00M 1.380(8) . ?
C00F C00J 1.324(8) . ?
C00H N00I 1.129(7) . ?
C00J C00N 1.409(9) . ?
C00J H24 0.9300 . ?
C00K C00P 1.385(11) . ?
C00K H17 0.9300 . ?
C00L C00N 1.355(9) . ?
C00L C00V 1.391(13) . ?
C00M C00R 1.377(11) . ?
C00M H20 1.00(4) . ?
C00N C00X 1.427(12) . ?
C00O C00U 1.470(6) . ?
C00O H12 0.9700 . ?
C00O H29 0.9700 . ?
C00P C00Q 1.365(11) . ?
C00P H16 0.92(4) . ?
C00Q C00R 1.347(11) . ?
C00Q H18 0.97(6) . ?
C00R H19 0.93(5) . ?
C00S C00W 1.433(6) . ?
C00S H10 0.9700 . ?
C00S H11 0.9700 . ?
C00T C00Y 1.276(12) . ?
C00T C00V 1.445(13) . ?
C00T H27 1.09(5) . ?
C00U H14 0.9600 . ?
C00U H13 0.9600 . ?
C00U H15 0.9600 . ?
C00V H28 1.11(4) . ?
C00V H27 1.49(5) . ?
C00W H8 0.9600 . ?
C00W H7 0.9600 . ?
C00W H9 0.9600 . ?
C00X C00Y 1.365(10) . ?
C00X H25 0.9300 . ?
C00Y H26 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
C00D O001 C00O 116.6(5) . . ?
C00F O003 C00L 103.9(8) . . ?
C00A N1 C1 118.8(8) . . ?
C00A N1 C00E 120.6(10) . . ?
C1 N1 C00E 120.6(10) . . ?
C00G O1 C00S 118.9(7) . . ?
C00A N007 H21 120.0 . . ?
C00A N007 H22 120.0 . . ?
H21 N007 H22 120.0 . . ?
C00C C1 N1 122.7(9) . . ?
C00C C1 C00D 123.0(11) . . ?
N1 C1 C00D 114.2(11) . . ?
C00A C009 C00H 118.7(9) . . ?
C00A C009 C00B 120.6(8) . . ?
C00H C009 C00B 120.1(9) . . ?
N007 C00A C009 122.5(10) . . ?
N007 C00A N1 115.8(11) . . ?
C009 C00A N1 121.8(8) . . ?
C00F C00B C009 112.4(7) . . ?
C00F C00B C00C 110.5(7) . . ?
C009 C00B C00C 111.5(8) . . ?
C00F C00B H00B 107.4 . . ?
C009 C00B H00B 107.4 . . ?
C00C C00B H00B 107.4 . . ?
C1 C00C C00G 123.7(10) . . ?
C1 C00C C00B 120.7(9) . . ?
C00G C00C C00B 115.6(12) . . ?
O002 C00D O001 126.3(8) . . ?
O002 C00D C1 123.1(7) . . ?
O001 C00D C1 110.5(7) . . ?
C00K C00E C00M 120.5(10) . . ?
C00K C00E N1 119.9(13) . . ?
C00M C00E N1 119.6(14) . . ?
C00J C00F O003 110.9(7) . . ?
C00J C00F C00B 133.4(12) . . ?
O003 C00F C00B 115.7(12) . . ?
O006 C00G O1 121.6(9) . . ?
O006 C00G C00C 123.4(10) . . ?
O1 C00G C00C 114.9(8) . . ?
N00I C00H C009 179.0(6) . . ?
C00F C00J C00N 109.1(8) . . ?
C00F C00J H24 125.4 . . ?
C00N C00J H24 125.4 . . ?
C00E C00K C00P 119.3(10) . . ?
C00E C00K H17 120.3 . . ?
C00P C00K H17 120.3 . . ?
C00N C00L C00V 126.2(18) . . ?
C00N C00L O003 111.6(10) . . ?
C00V C00L O003 122.2(18) . . ?
C00R C00M C00E 119.2(10) . . ?
C00R C00M H20 126(3) . . ?
C00E C00M H20 115(3) . . ?
C00L C00N C00J 104.5(11) . . ?
C00L C00N C00X 117.4(17) . . ?
C00J C00N C00X 138.1(19) . . ?
O001 C00O C00U 111.1(4) . . ?
O001 C00O H12 109.4 . . ?
C00U C00O H12 109.4 . . ?
O001 C00O H29 109.4 . . ?
C00U C00O H29 109.4 . . ?
H12 C00O H29 108.0 . . ?
C00Q C00P C00K 120.4(12) . . ?
C00Q C00P H16 124(4) . . ?
C00K C00P H16 115(4) . . ?
C00R C00Q C00P 119.9(14) . . ?
C00R C00Q H18 123(4) . . ?
C00P C00Q H18 117(4) . . ?
C00Q C00R C00M 120.7(12) . . ?
C00Q C00R H19 119(4) . . ?
C00M C00R H19 120(4) . . ?
C00W C00S O1 108.6(6) . . ?
C00W C00S H10 110.0 . . ?
O1 C00S H10 110.0 . . ?
C00W C00S H11 110.0 . . ?
O1 C00S H11 110.0 . . ?
H10 C00S H11 108.3 . . ?
C00Y C00T C00V 121.9(17) . . ?
C00Y C00T H27 165(3) . . ?
C00V C00T H27 70(3) . . ?
C00O C00U H14 109.5 . . ?
C00O C00U H13 109.5 . . ?
H14 C00U H13 109.5 . . ?
C00O C00U H15 109.5 . . ?
H14 C00U H15 109.5 . . ?
H13 C00U H15 109.5 . . ?
C00L C00V C00T 112.4(15) . . ?
C00L C00V H28 108(3) . . ?
C00T C00V H28 139(3) . . ?
C00L C00V H27 154(3) . . ?
C00T C00V H27 44(2) . . ?
H28 C00V H27 95(3) . . ?
C00S C00W H8 109.5 . . ?
C00S C00W H7 109.5 . . ?
H8 C00W H7 109.5 . . ?
C00S C00W H9 109.5 . . ?
H8 C00W H9 109.5 . . ?
H7 C00W H9 109.5 . . ?
C00Y C00X C00N 116.5(11) . . ?
C00Y C00X H25 121.7 . . ?
C00N C00X H25 121.8 . . ?
C00T C00Y C00X 125.6(16) . . ?
C00T C00Y H26 117.2 . . ?
C00X C00Y H26 117.2 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.019


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_mo_NITK352_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1423055'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Diethyl 6-amino-4-(benzofuran-2-yl)-5-cyano-1-p-tolyl-1,4-dihydropyridine-2,3-dicarboxylate '
_chemical_name_common            ?
_chemical_melting_point          218-219C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N3 O5'
_chemical_formula_weight         471.50

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

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

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

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

_cell_length_a                   9.9491(3)
_cell_length_b                   11.8834(4)
_cell_length_c                   12.5820(4)
_cell_angle_alpha                112.9320(10)
_cell_angle_beta                 99.2640(10)
_cell_angle_gamma                109.5870(10)
_cell_volume                     1215.64(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8674
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         14.995
_diffrn_reflns_theta_full        14.995
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             982
_reflns_number_gt                959
_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)+(0.0441P)²+1.7404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         982
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          2.424
_refine_ls_shift/su_mean         0.053

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
O5 O 0.5259(14) 0.8582(7) 0.7345(9) 0.0397(15) Uani 1 1 d . . . . .
N1 N 0.257(3) 0.928(2) 0.8382(17) 0.045(4) Uani 1 1 d . . . . .
O2 O 0.0100(7) 0.4096(5) 0.6550(3) 0.0579(17) Uani 1 1 d . . . . .
O1 O 0.2532(6) 0.4520(6) 0.7264(4) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.2133(5) 0.7148(14) 0.7644(13) 0.034(2) Uani 1 1 d . . . . .
O4 O 0.2865(6) 0.4952(7) 0.3880(8) 0.065(2) Uani 1 1 d . . . . .
O3 O 0.1576(5) 0.3653(6) 0.4594(5) 0.076(2) Uani 1 1 d . . . . .
C16 C 0.2300(7) 0.8267(15) 0.7499(12) 0.048(3) Uani 1 1 d . . . . .
C22 C 0.681(2) 0.9205(10) 0.762(2) 0.035(2) Uani 1 1 d . . . . .
C1 C 0.2012(7) 0.6013(14) 0.6642(19) 0.029(2) Uani 1 1 d . . . . .
N3 N 0.2856(7) 1.0452(7) 0.6256(5) 0.068(2) Uani 1 1 d . . . . .
C19 C 0.4557(17) 0.8080(8) 0.6091(14) 0.035(2) Uani 1 1 d . . . . .
C9 C 0.234(2) 0.7261(11) 0.8855(14) 0.034(2) Uani 1 1 d . . . . .
C18 C 0.2892(13) 0.7334(12) 0.5604(10) 0.034(2) Uani 1 1 d . . . . .
C17 C 0.2051(7) 0.8116(10) 0.6217(9) 0.036(2) Uani 1 1 d . . . . .
C2 C 0.2343(7) 0.5996(13) 0.5653(17) 0.032(3) Uani 1 1 d . . . . .
C21 C 0.707(2) 0.9092(10) 0.654(2) 0.037(2) Uani 1 1 d . . . . .
C27 C 0.2536(7) 0.9439(12) 0.6264(5) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.1444(14) 0.4756(10) 0.6799(7) 0.043(2) Uani 1 1 d . . . . .
C14 C 0.3754(16) 0.7863(8) 0.9715(18) 0.046(3) Uani 1 1 d . . . . .
C3 C 0.2215(9) 0.4778(14) 0.4670(14) 0.047(2) Uani 1 1 d . . . . .
C20 C 0.564(3) 0.8385(11) 0.5599(11) 0.044(2) Uani 1 1 d . . . . .
C23 C 0.791(3) 0.9814(12) 0.8729(15) 0.050(3) Uani 1 1 d . . . . .
C10 C 0.1066(18) 0.6696(9) 0.9102(15) 0.050(2) Uani 1 1 d . . . . .
C12 C 0.263(2) 0.7326(11) 1.1117(12) 0.053(3) Uani 1 1 d . . . . .
C13 C 0.3871(17) 0.7883(9) 1.0830(16) 0.053(3) Uani 1 1 d . . . . .
C24 C 0.937(2) 1.0321(9) 0.8722(15) 0.058(3) Uani 1 1 d . . . . .
C11 C 0.1227(19) 0.6725(9) 1.023(2) 0.056(3) Uani 1 1 d . . . . .
C28 C 0.855(3) 0.9615(13) 0.6574(15) 0.054(3) Uani 1 1 d . . . . .
C25 C 0.9693(17) 1.0222(10) 0.767(2) 0.059(2) Uani 1 1 d . . . . .
C15 C 0.2852(18) 0.7432(13) 1.2378(11) 0.088(3) Uani 1 1 d . . . . .
H17 H 0.192(8) 0.305(8) 0.250(7) 0.13(5) Uiso 1 1 d . . . . .
C7 C 0.2093(14) 0.3351(13) 0.7506(15) 0.105(4) Uani 1 1 d . . . . .
C5 C 0.3524(15) 0.4103(12) 0.2101(14) 0.127(4) Uani 1 1 d . . . . .
C8 C 0.3100(17) 0.3782(18) 0.8681(16) 0.147(6) Uani 1 1 d . . . . .
H6 H 0.208(9) 0.672(9) 1.236(8) 0.16(5) Uiso 1 1 d . . . . .
H30 H 0.541(7) 0.818(5) 0.478(5) 0.05(3) Uiso 1 1 d . . . . .
H7 H 0.260(5) 0.711(4) 0.473(5) 0.02(2) Uiso 1 1 d . . . . .
H5 H 0.007(7) 0.627(5) 0.850(6) 0.07(3) Uiso 1 1 d . . . . .
H4 H 0.462(8) 0.826(6) 0.950(6) 0.08(4) Uiso 1 1 d . . . . .
H2 H 1.074(8) 1.059(6) 0.771(6) 0.08(4) Uiso 1 1 d . . . . .
H3 H 0.764(7) 0.988(6) 0.947(6) 0.08(4) Uiso 1 1 d . . . . .
H35 H 0.879(6) 0.954(5) 0.584(5) 0.05(3) Uiso 1 1 d . . . . .
H8 H 0.487(6) 0.831(5) 1.142(5) 0.05(3) Uiso 1 1 d . . . . .
H11 H 0.034(6) 0.638(5) 1.041(5) 0.04(3) Uiso 1 1 d . . . . .
H9 H 1.010(6) 1.071(5) 0.947(5) 0.04(3) Uiso 1 1 d . . . . .
C29 C 0.2907(17) 0.3761(13) 0.2960(13) 0.092(3) Uani 1 1 d . . . . .
H14 H 0.360(10) 0.719(10) 1.258(8) 0.18(6) Uiso 1 1 d . . . . .
H18 H 0.287(19) 0.428(16) 0.918(14) 0.31(13) Uiso 1 1 d . . . . .
H19 H 0.274(12) 0.817(11) 1.294(11) 0.26(7) Uiso 1 1 d . . . . .
H22 H 0.287(11) 0.443(10) 0.178(9) 0.20(6) Uiso 1 1 d . . . . .
H28 H 0.205(13) 0.267(12) 0.685(10) 0.22(7) Uiso 1 1 d . . . . .
H29 H 0.100(18) 0.311(15) 0.750(13) 0.36(10) Uiso 1 1 d . . . . .
H23 H 0.280(12) 0.983(7) 0.850(8) 0.00(3) Uiso 1 1 d . . . . .
H24 H 0.220(11) 0.952(16) 0.831(7) 0.00(3) Uiso 1 1 d . . . . .
H31 H 0.449(8) 0.443(6) 0.313(7) 0.12(3) Uiso 1 1 d . . . . .
H26 H 0.296(7) 0.319(7) 0.890(7) 0.10(3) Uiso 1 1 d . . . . .
H33 H 0.368(11) 0.358(9) 0.348(7) 0.18(5) Uiso 1 1 d . . . . .
H36 H 0.365(10) 0.339(9) 0.152(9) 0.18(5) Uiso 1 1 d . . . . .
H32 H 0.38(2) 0.350(19) 0.79(2) 0.48(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
O5 C22 1.383(10) . ?
O5 C19 1.402(8) . ?
N1 C16 1.183(16) . ?
N1 H23 0.57(7) . ?
N1 H24 0.55(8) . ?
O2 C6 1.214(8) . ?
O1 C6 1.312(8) . ?
O1 C7 1.475(9) . ?
N2 C16 1.371(12) . ?
N2 C1 1.393(11) . ?
N2 C9 1.451(12) . ?
O4 C3 1.314(10) . ?
O4 C29 1.457(9) . ?
O3 C3 1.229(10) . ?
C16 C17 1.521(15) . ?
C16 H24 1.49(12) . ?
C22 C23 1.368(10) . ?
C22 C21 1.382(11) . ?
C1 C2 1.333(10) . ?
C1 C6 1.512(12) . ?
N3 C27 1.142(9) . ?
C19 C20 1.341(10) . ?
C19 C18 1.474(11) . ?
C9 C10 1.369(10) . ?
C9 C14 1.375(10) . ?
C18 C2 1.528(11) . ?
C18 C17 1.526(8) . ?
C18 H7 1.00(5) . ?
C17 C27 1.455(10) . ?
C2 C3 1.440(11) . ?
C21 C28 1.381(12) . ?
C21 C20 1.423(12) . ?
C14 C13 1.380(11) . ?
C14 H4 0.97(6) . ?
C20 H30 0.93(5) . ?
C23 C24 1.377(12) . ?
C23 H3 0.99(6) . ?
C10 C11 1.382(11) . ?
C10 H5 0.97(6) . ?
C12 C13 1.369(11) . ?
C12 C11 1.386(11) . ?
C12 C15 1.514(14) . ?
C13 H8 0.96(5) . ?
C24 C25 1.386(11) . ?
C24 H9 0.92(5) . ?
C11 H11 0.95(5) . ?
C28 C25 1.368(11) . ?
C28 H35 0.96(5) . ?
C25 H2 0.96(6) . ?
C15 H6 0.92(9) . ?
C15 H14 0.91(9) . ?
C15 H19 0.94(12) . ?
C7 C8 1.428(14) . ?
C7 H28 0.88(11) . ?
C7 H29 1.02(15) . ?
C5 C29 1.449(12) . ?
C5 H22 0.97(9) . ?
C5 H31 1.31(7) . ?
C5 H36 0.93(9) . ?
C8 H18 0.81(16) . ?
C8 H26 0.84(7) . ?
C8 H32 1.3(2) . ?
C29 H17 0.94(7) . ?
C29 H31 1.45(7) . ?
C29 H33 1.06(9) . ?

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
C22 O5 C19 108.4(10) . . ?
C16 N1 H23 134(9) . . ?
C16 N1 H24 113(10) . . ?
H23 N1 H24 58(8) . . ?
C6 O1 C7 117.6(8) . . ?
C16 N2 C1 117.1(12) . . ?
C16 N2 C9 119.5(12) . . ?
C1 N2 C9 122.6(11) . . ?
C3 O4 C29 116.7(10) . . ?
N1 C16 N2 117.2(18) . . ?
N1 C16 C17 124.2(16) . . ?
N2 C16 C17 118.5(11) . . ?
N1 C16 H24 20(3) . . ?
N2 C16 H24 129(4) . . ?
C17 C16 H24 110(4) . . ?
C23 C22 C21 125.0(15) . . ?
C23 C22 O5 127.5(19) . . ?
C21 C22 O5 107.5(16) . . ?
C2 C1 N2 125.7(12) . . ?
C2 C1 C6 122.7(12) . . ?
N2 C1 C6 111.7(15) . . ?
C20 C19 O5 108.4(10) . . ?
C20 C19 C18 134.7(15) . . ?
O5 C19 C18 117.0(16) . . ?
C10 C9 C14 120.7(12) . . ?
C10 C9 N2 117.2(16) . . ?
C14 C9 N2 122.1(17) . . ?
C19 C18 C2 111.8(8) . . ?
C19 C18 C17 115.5(8) . . ?
C2 C18 C17 107.9(9) . . ?
C19 C18 H7 105(3) . . ?
C2 C18 H7 108(3) . . ?
C17 C18 H7 108(3) . . ?
C27 C17 C16 110.7(9) . . ?
C27 C17 C18 112.5(8) . . ?
C16 C17 C18 108.2(8) . . ?
C1 C2 C3 121.9(12) . . ?
C1 C2 C18 117.4(12) . . ?
C3 C2 C18 120.7(12) . . ?
C28 C21 C22 118.4(16) . . ?
C28 C21 C20 134(2) . . ?
C22 C21 C20 107.4(15) . . ?
N3 C27 C17 176.8(7) . . ?
O2 C6 O1 125.5(10) . . ?
O2 C6 C1 120.8(10) . . ?
O1 C6 C1 113.5(9) . . ?
C9 C14 C13 119.0(11) . . ?
C9 C14 H4 117(4) . . ?
C13 C14 H4 124(4) . . ?
O3 C3 O4 122.2(12) . . ?
O3 C3 C2 122.2(11) . . ?
O4 C3 C2 115.6(12) . . ?
C19 C20 C21 108.3(11) . . ?
C19 C20 H30 122(4) . . ?
C21 C20 H30 129(4) . . ?
C22 C23 C24 114.8(12) . . ?
C22 C23 H3 121(4) . . ?
C24 C23 H3 125(4) . . ?
C9 C10 C11 118.7(12) . . ?
C9 C10 H5 121(4) . . ?
C11 C10 H5 120(4) . . ?
C13 C12 C11 116.8(12) . . ?
C13 C12 C15 119.2(17) . . ?
C11 C12 C15 124.0(17) . . ?
C12 C13 C14 122.5(11) . . ?
C12 C13 H8 120(4) . . ?
C14 C13 H8 118(4) . . ?
C23 C24 C25 122.3(11) . . ?
C23 C24 H9 114(4) . . ?
C25 C24 H9 124(4) . . ?
C10 C11 C12 122.4(11) . . ?
C10 C11 H11 118(4) . . ?
C12 C11 H11 119(4) . . ?
C25 C28 C21 118.7(11) . . ?
C25 C28 H35 120(4) . . ?
C21 C28 H35 121(4) . . ?
C28 C25 C24 120.8(10) . . ?
C28 C25 H2 120(4) . . ?
C24 C25 H2 119(4) . . ?
C12 C15 H6 111(6) . . ?
C12 C15 H14 111(6) . . ?
H6 C15 H14 95(7) . . ?
C12 C15 H19 113(7) . . ?
H6 C15 H19 101(8) . . ?
H14 C15 H19 123(10) . . ?
C8 C7 O1 107.6(11) . . ?
C8 C7 H28 120(8) . . ?
O1 C7 H28 105(8) . . ?
C8 C7 H29 111(9) . . ?
O1 C7 H29 106(8) . . ?
H28 C7 H29 106(10) . . ?
C29 C5 H22 105(6) . . ?
C29 C5 H31 63(3) . . ?
H22 C5 H31 140(7) . . ?
C29 C5 H36 113(6) . . ?
H22 C5 H36 117(8) . . ?
H31 C5 H36 103(6) . . ?
C7 C8 H18 107(10) . . ?
C7 C8 H26 116(5) . . ?
H18 C8 H26 99(10) . . ?
C7 C8 H32 71(10) . . ?
H18 C8 H32 154(10) . . ?
H26 C8 H32 105(10) . . ?
C5 C29 O4 109.3(11) . . ?
C5 C29 H17 106(5) . . ?
O4 C29 H17 111(5) . . ?
C5 C29 H31 54(3) . . ?
O4 C29 H31 95(3) . . ?
H17 C29 H31 152(6) . . ?
C5 C29 H33 110(5) . . ?
O4 C29 H33 103(5) . . ?
H17 C29 H33 118(7) . . ?
H31 C29 H33 63(5) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.025


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
