# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_SS-153-A
_database_code_depnum_ccdc_archive 'CCDC 1850643'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N,2,4-Trimethylfuran-3-carboxamide
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N O2'
_chemical_formula_weight         153.18

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.0234(15)
_cell_length_b                   12.137(4)
_cell_length_c                   13.751(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.80(2)
_cell_angle_gamma                90
_cell_volume                     826.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3514
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      24.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7928
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.503
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             2772
_reflns_number_gt                2172
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.904

_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)+(0.0500P)²+0.1000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2772
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
O1 O 0.1557(5) 0.6221(2) 1.11587(18) 0.0626(7) Uani 1 1 d . . . . .
O2 O 0.0062(9) 0.6281(3) 0.4360(3) 0.1113(12) Uani 1 1 d . . . . .
N2 N 0.0372(6) 0.4359(2) 0.8467(2) 0.0484(7) Uani 1 1 d . . . . .
N1 N 0.1643(6) 0.2792(3) 0.3393(2) 0.0551(8) Uani 1 1 d . . . . .
O3 O 0.4800(4) 0.4691(2) 0.85951(18) 0.0633(7) Uani 1 1 d . . . . .
O4 O -0.2754(5) 0.3117(2) 0.3329(2) 0.0712(8) Uani 1 1 d . . . . .
C10 C 0.2647(6) 0.4836(3) 0.8898(2) 0.0432(7) Uani 1 1 d . . . . .
C2 C -0.0392(6) 0.3420(3) 0.3564(2) 0.0505(8) Uani 1 1 d . . . . .
C11 C 0.2486(6) 0.5552(3) 0.9751(2) 0.0437(8) Uani 1 1 d . . . . .
C12 C 0.1129(6) 0.5367(3) 1.0514(2) 0.0480(8) Uani 1 1 d . . . . .
C16 C 0.5575(7) 0.7182(3) 0.9327(3) 0.0685(11) Uani 1 1 d . . . . .
H16A H 0.5974 0.7908 0.9589 0.103 Uiso 1 1 calc R U . . .
H16B H 0.4633 0.7236 0.8660 0.103 Uiso 1 1 calc R U . . .
H16C H 0.7228 0.6783 0.9338 0.103 Uiso 1 1 calc R U . . .
C9 C 0.0277(8) 0.3650(4) 0.7614(3) 0.0650(10) Uani 1 1 d . . . . .
H9A H 0.0547 0.4083 0.7055 0.097 Uiso 1 1 calc R U . . .
H9B H -0.1452 0.3293 0.7475 0.097 Uiso 1 1 calc R U . . .
H9C H 0.1673 0.3103 0.7748 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3845(6) 0.6591(3) 0.9941(3) 0.0509(9) Uani 1 1 d . . . . .
C3 C 0.0312(7) 0.4494(3) 0.4036(2) 0.0524(9) Uani 1 1 d . . . . .
C4 C 0.2416(7) 0.4751(4) 0.4823(3) 0.0670(11) Uani 1 1 d . . . . .
C13 C -0.0535(7) 0.4454(3) 1.0792(3) 0.0597(9) Uani 1 1 d . . . . .
H13A H 0.0184 0.4213 1.1450 0.090 Uiso 1 1 calc R U . . .
H13B H -0.0512 0.3853 1.0341 0.090 Uiso 1 1 calc R U . . .
H13C H -0.2359 0.4704 1.0768 0.090 Uiso 1 1 calc R U . . .
C1 C 0.1234(8) 0.1729(4) 0.2931(3) 0.0746(12) Uani 1 1 d . . . . .
H1A H 0.0402 0.1244 0.3343 0.112 Uiso 1 1 calc R U . . .
H1B H 0.2943 0.1429 0.2841 0.112 Uiso 1 1 calc R U . . .
H1C H 0.0082 0.1802 0.2302 0.112 Uiso 1 1 calc R U . . .
C15 C 0.3193(7) 0.6959(3) 1.0792(3) 0.0598(10) Uani 1 1 d . . . . .
H15 H 0.3775 0.7624 1.1091 0.072 Uiso 1 1 calc R U . . .
C6 C -0.1082(8) 0.5462(4) 0.3790(3) 0.0693(11) Uani 1 1 d . . . . .
C5 C 0.2299(10) 0.5807(4) 0.5026(4) 0.0801(13) Uani 1 1 d . . . . .
H5 H 0.3457 0.6183 0.5514 0.096 Uiso 1 1 calc R U . . .
C8 C 0.4462(8) 0.4011(4) 0.5409(3) 0.0852(15) Uani 1 1 d . . . . .
H8A H 0.5875 0.3858 0.5038 0.128 Uiso 1 1 calc R U . . .
H8B H 0.3612 0.3334 0.5547 0.128 Uiso 1 1 calc R U . . .
H8C H 0.5214 0.4365 0.6018 0.128 Uiso 1 1 calc R U . . .
C7 C -0.3449(9) 0.5724(4) 0.3028(4) 0.0861(14) Uani 1 1 d . . . . .
H7A H -0.4547 0.6265 0.3280 0.129 Uiso 1 1 calc R U . . .
H7B H -0.4490 0.5067 0.2857 0.129 Uiso 1 1 calc R U . . .
H7C H -0.2845 0.6009 0.2451 0.129 Uiso 1 1 calc R U . . .
H2N H -0.100(7) 0.451(3) 0.866(2) 0.039(9) Uiso 1 1 d . . . . .
H1N H 0.328(7) 0.305(3) 0.348(2) 0.054(10) 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
O1 C12 1.358(4) . ?
O1 C15 1.369(4) . ?
O2 C6 1.334(5) . ?
O2 C5 1.443(6) . ?
N2 C10 1.327(4) . ?
N2 C9 1.449(4) . ?
N1 C2 1.328(4) . ?
N1 C1 1.437(5) . ?
O3 C10 1.236(3) . ?
O4 C2 1.232(4) . ?
C10 C11 1.474(4) . ?
C2 C3 1.472(5) . ?
C11 C12 1.364(5) . ?
C11 C14 1.436(5) . ?
C12 C13 1.477(5) . ?
C16 C14 1.494(5) . ?
C14 C15 1.344(5) . ?
C3 C6 1.380(6) . ?
C3 C4 1.413(5) . ?
C4 C5 1.315(6) . ?
C4 C8 1.493(6) . ?
C6 C7 1.479(6) . ?

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
C12 O1 C15 107.3(3) . . ?
C6 O2 C5 106.7(4) . . ?
C10 N2 C9 121.8(3) . . ?
C2 N1 C1 122.5(3) . . ?
O3 C10 N2 121.6(3) . . ?
O3 C10 C11 121.5(3) . . ?
N2 C10 C11 116.9(3) . . ?
O4 C2 N1 121.2(4) . . ?
O4 C2 C3 121.9(3) . . ?
N1 C2 C3 116.9(3) . . ?
C12 C11 C14 106.8(3) . . ?
C12 C11 C10 128.1(3) . . ?
C14 C11 C10 125.0(3) . . ?
O1 C12 C11 109.4(3) . . ?
O1 C12 C13 116.0(3) . . ?
C11 C12 C13 134.6(3) . . ?
C15 C14 C11 105.8(3) . . ?
C15 C14 C16 125.7(3) . . ?
C11 C14 C16 128.5(3) . . ?
C6 C3 C4 106.4(4) . . ?
C6 C3 C2 124.9(3) . . ?
C4 C3 C2 128.7(3) . . ?
C5 C4 C3 108.9(4) . . ?
C5 C4 C8 121.6(4) . . ?
C3 C4 C8 129.5(4) . . ?
C14 C15 O1 110.7(3) . . ?
O2 C6 C3 109.9(4) . . ?
O2 C6 C7 118.0(4) . . ?
C3 C6 C7 132.1(4) . . ?
C4 C5 O2 108.2(4) . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
