# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_mo_DT95_0ma
_database_code_depnum_ccdc_archive 'CCDC 1527924'

_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_publcif_datablock.id            {3912ed6f-5141-4bf3-993c-1fef587efc1e}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (2E,4E)-5-(pyridin-3-yl)penta-2,4-dienal
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C10H9NO
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.19

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                   9.8131(9)
_cell_length_b                   11.6684(12)
_cell_length_c                   7.2988(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.827(3)
_cell_angle_gamma                90
_cell_volume                     823.47(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20110
_cell_measurement_theta_min      0.1
_cell_measurement_theta_max      54

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       multi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33032
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.736
_diffrn_reflns_theta_max         28.785
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2135
_reflns_number_gt                1536
_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)+(0.0528P)²+0.3100P] 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         2135
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1064
_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 0.45822(15) 0.27969(12) 0.64051(19) 0.0204(3) Uani 1 1 d . . . . .
H1 H 0.5315 0.3281 0.6966 0.024 Uiso 1 1 calc R U . . .
C2 C 0.33542(14) 0.33195(12) 0.55715(19) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.22680(14) 0.25979(12) 0.47868(19) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.1409 0.2910 0.4203 0.023 Uiso 1 1 calc R U . . .
C5 C 0.37415(15) 0.10035(12) 0.5711(2) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.3869 0.0196 0.5745 0.026 Uiso 1 1 calc R U . . .
C4 C 0.24677(15) 0.14249(12) 0.48767(19) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.1743 0.0917 0.4374 0.025 Uiso 1 1 calc R U . . .
C6 C 0.32441(14) 0.45685(12) 0.55812(19) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.3986 0.4974 0.6306 0.022 Uiso 1 1 calc R U . . .
C7 C 0.22043(14) 0.51973(12) 0.46732(19) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.1448 0.4821 0.3927 0.023 Uiso 1 1 calc R U . . .
C8 C 0.21980(14) 0.64286(12) 0.47940(19) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.2952 0.6783 0.5578 0.022 Uiso 1 1 calc R U . . .
C9 C 0.12085(15) 0.71157(12) 0.3884(2) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.0433 0.6789 0.3100 0.024 Uiso 1 1 calc R U . . .
C10 C 0.13135(15) 0.83521(12) 0.4087(2) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.2105 0.8647 0.4879 0.025 Uiso 1 1 calc R U . . .
N11 N 0.48069(13) 0.16642(11) 0.64754(17) 0.0236(3) Uani 1 1 d . . . . .
O12 O 0.04723(11) 0.90405(9) 0.33279(15) 0.0263(3) 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 N11 1.3395(19) . ?
C1 C2 1.3942(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.4017(19) . ?
C2 C6 1.461(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C5 N11 1.3414(18) . ?
C5 C4 1.384(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C6 C7 1.3372(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.439(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3442(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.452(2) . ?
C9 H9 0.9500 . ?
C10 O12 1.2156(17) . ?
C10 H10 0.9500 . ?

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
N11 C1 C2 124.94(13) . . ?
N11 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C1 C2 C3 117.13(13) . . ?
C1 C2 C6 119.55(13) . . ?
C3 C2 C6 123.32(13) . . ?
C4 C3 C2 118.91(13) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N11 C5 C4 124.07(13) . . ?
N11 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C3 C4 C5 118.86(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C7 C6 C2 126.56(13) . . ?
C7 C6 H6 116.7 . . ?
C2 C6 H6 116.7 . . ?
C6 C7 C8 121.89(13) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 125.12(13) . . ?
C9 C8 H8 117.4 . . ?
C7 C8 H8 117.4 . . ?
C8 C9 C10 120.62(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O12 C10 C9 125.38(13) . . ?
O12 C10 H10 117.3 . . ?
C9 C10 H10 117.3 . . ?
C1 N11 C5 116.08(12) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylacetate'
_chemical_properties_physical    ', Moisture-sensitive,Oxygen-sensitive'
