# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_20161027a
_database_code_depnum_ccdc_archive 'CCDC 1533695'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;
_audit_creation_date             2016-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H13 N O'
_chemical_formula_sum            'C6 H13 N O'
_chemical_formula_weight         115.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.55642(18)
_cell_length_b                   4.79489(14)
_cell_length_c                   26.6236(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.307(3)
_cell_angle_gamma                90
_cell_volume                     708.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      6.6430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.230
_diffrn_reflns_theta_min         6.662
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00   5.00   1.00    1.00    --  -41.74  37.00   0.00   57
  2  ω    -70.00  26.00   1.00    1.00    --  -41.74  57.00-120.00   96
  3  ω   -106.00 -18.00   1.00    1.00    --  -41.74 -57.00  90.00   88
  4  ω   -114.00 -54.00   1.00    1.00    --  -41.74-159.00-109.00   60
  5  ω     66.00  95.00   1.00    1.00    --   41.74-125.00-180.00   29
  6  ω     65.00 109.00   1.00    1.00    --  107.19 -94.00 -60.00   44
  7  ω     82.00 138.00   1.00    1.00    --  107.19 -77.00 -30.00   56
  8  ω     98.00 124.00   1.00    1.00    --  107.19 -45.00   0.00   26
  9  ω     79.00 153.00   1.00    1.00    --  107.19  30.00  30.00   74
 10  ω     42.00 125.00   1.00    1.00    --  107.19 -77.00-180.00   83
 11  ω     52.00 115.00   1.00    1.00    --  107.19-125.00-180.00   63
 12  ω     45.00 118.00   1.00    1.00    --  107.19 -30.00-150.00   73
 13  ω     36.00  65.00   1.00    1.00    --  107.19 -45.00   0.00   29
 14  ω     35.00 145.00   1.00    1.00    --  107.19 -15.00   0.00  110
 15  ω     34.00 130.00   1.00    1.00    --  107.19 -30.00 120.00   96
 16  ω     34.00  60.00   1.00    1.00    --  107.19 -94.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2676489000
_diffrn_orient_matrix_UB_12      -0.0787264000
_diffrn_orient_matrix_UB_13      -0.0030475000
_diffrn_orient_matrix_UB_21      -0.0205885000
_diffrn_orient_matrix_UB_22      0.0467009000
_diffrn_orient_matrix_UB_23      -0.0573336000
_diffrn_orient_matrix_UB_31      0.0715198000
_diffrn_orient_matrix_UB_32      0.3079080000
_diffrn_orient_matrix_UB_33      0.0079031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1304
_reflns_number_total             1386
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.1861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.18747(11) 0.40353(14) 0.28095(2) 0.0193(2) Uani 1 1 d . . . . .
H1 H 0.0700 0.3453 0.2640 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.20300(13) 0.69374(17) 0.27557(3) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.38769(16) 0.7933(2) 0.30006(3) 0.0167(2) Uani 1 1 d . . . . .
H1A H 0.4106 0.9850 0.2981 0.020 Uiso 1 1 calc R . . . .
C2 C 0.57075(16) 0.6328(2) 0.33158(3) 0.0162(2) Uani 1 1 d . . . . .
H2A H 0.6653 0.5198 0.3098 0.019 Uiso 1 1 calc R . . . .
H2B H 0.4883 0.5078 0.3535 0.019 Uiso 1 1 calc R . . . .
C3 C 0.73991(16) 0.8210(2) 0.36357(3) 0.0176(2) Uani 1 1 d . . . . .
H3A H 0.8241 0.9441 0.3416 0.021 Uiso 1 1 calc R . . . .
H3B H 0.6452 0.9358 0.3850 0.021 Uiso 1 1 calc R . . . .
C4 C 0.92426(16) 0.6566(2) 0.39625(3) 0.0184(2) Uani 1 1 d . . . . .
H4A H 0.8398 0.5321 0.4179 0.022 Uiso 1 1 calc R . . . .
H4B H 1.0196 0.5430 0.3747 0.022 Uiso 1 1 calc R . . . .
C5 C 1.09249(19) 0.8423(2) 0.42866(4) 0.0266(3) Uani 1 1 d . . . . .
H5A H 0.9972 0.9562 0.4502 0.032 Uiso 1 1 calc R . . . .
H5B H 1.1774 0.9664 0.4070 0.032 Uiso 1 1 calc R . . . .
C6 C 1.27629(19) 0.6771(3) 0.46139(4) 0.0303(3) Uani 1 1 d . . . . .
H6A H 1.3753 0.5692 0.4403 0.046 Uiso 1 1 calc GR . . . .
H6B H 1.1935 0.5546 0.4831 0.046 Uiso 1 1 calc GR . . . .
H6C H 1.3757 0.8036 0.4814 0.046 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 N1 1.4020(10) . ?
N1 C1 1.2763(12) . ?
C1 H1A 0.9300 . ?
C1 C2 1.4942(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.5268(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5245(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5224(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5253(14) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
N1 O1 H1 109.5 . . ?
C1 N1 O1 111.80(7) . . ?
N1 C1 H1A 116.7 . . ?
N1 C1 C2 126.56(9) . . ?
C2 C1 H1A 116.7 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.71(8) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.62(8) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 113.06(9) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C4 C5 C6 112.91(10) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O1 N1 C1 C2 -0.42(12) . . . . ?
N1 C1 C2 C3 -168.88(8) . . . . ?
C1 C2 C3 C4 179.19(7) . . . . ?
C2 C3 C4 C5 -179.49(7) . . . . ?
C3 C4 C5 C6 179.87(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.498
_oxdiff_exptl_absorpt_empirical_full_min 0.608
