# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_NH3OH-OAc
_database_code_depnum_ccdc_archive 'CCDC 1559355'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H7 N O3'
_chemical_formula_weight         93.09

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                   7.3033(5)
_cell_length_b                   8.6135(6)
_cell_length_c                   6.8992(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.565(3)
_cell_angle_gamma                90
_cell_volume                     427.97(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3507
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker AXScale'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6904
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.828
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1067
_reflns_number_gt                956
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0536P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1067
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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 0.95912(9) 0.29207(8) 0.17844(11) 0.01838(19) Uani 1 1 d . . . . .
O2 O 0.67773(9) 0.34910(8) 0.02342(11) 0.01835(19) Uani 1 1 d . . . . .
O3 O 0.36997(9) 0.28866(8) -0.18594(10) 0.01775(19) Uani 1 1 d . . . . .
H3 H 0.488(2) 0.3090(16) -0.108(2) 0.027 Uiso 1 1 d . U . . .
N2 N 0.23817(11) 0.34327(9) -0.07157(12) 0.0150(2) Uani 1 1 d . . . . .
H2A H 0.257(2) 0.3005(16) 0.045(2) 0.022 Uiso 1 1 d . U . . .
H2B H 0.2507(18) 0.4502(17) -0.0574(19) 0.022 Uiso 1 1 d . U . . .
H2C H 0.126(2) 0.3147(16) -0.139(2) 0.022 Uiso 1 1 d . U . . .
C1 C 0.75569(14) 0.08055(11) 0.06544(16) 0.0198(2) Uani 1 1 d . . . . .
H1A H 0.854(2) 0.0157(18) 0.127(2) 0.030 Uiso 1 1 d . U . . .
H1B H 0.730(2) 0.0570(17) -0.066(2) 0.030 Uiso 1 1 d . U . . .
H1C H 0.6482(19) 0.0580(18) 0.118(2) 0.030 Uiso 1 1 d . U . . .
C2 C 0.80312(12) 0.25054(11) 0.09249(13) 0.0142(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0135(3) 0.0176(4) 0.0225(4) 0.0009(3) -0.0017(3) -0.0006(2)
O2 0.0146(3) 0.0132(3) 0.0251(4) -0.0005(2) -0.0030(3) 0.0010(2)
O3 0.0122(3) 0.0212(4) 0.0192(4) -0.0047(3) 0.0010(3) 0.0003(2)
N2 0.0137(4) 0.0140(4) 0.0170(4) -0.0004(3) 0.0018(3) -0.0001(3)
C1 0.0210(5) 0.0128(4) 0.0248(5) -0.0003(3) 0.0013(4) -0.0004(3)
C2 0.0134(4) 0.0139(4) 0.0152(4) 0.0001(3) 0.0021(3) 0.0005(3)

_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 C2 1.2462(11) . ?
O2 C2 1.2812(11) . ?
O3 N2 1.4223(10) . ?
C1 C2 1.5090(13) . ?

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
O1 C2 O2 121.82(9) . . ?
O1 C2 C1 120.69(8) . . ?
O2 C2 C1 117.50(8) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052

_shelx_res_file                  
; 
  
    p1.res created by SHELXL-2014/7 
  
  
TITL p1 in P2(1)/c 
CELL 0.71073   7.30330   8.61350   6.89920  90.0000  99.5646  90.0000 
ZERR    4.00   0.00050   0.00060   0.00040   0.0000   0.0031   0.0000 
LATT  1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 8 28 4 12 
  
L.S. 10 
ACTA 
FMAP 2 
PLAN 5 
TEMP 23.000 
  
WGHT    0.053600    0.139800 
FVAR       0.39709 
O1    4    0.959116    0.292068    0.178441    11.00000    0.01346    0.01761 = 
         0.02248    0.00087   -0.00167   -0.00058 
O2    4    0.677730    0.349100    0.023421    11.00000    0.01460    0.01322 = 
         0.02508   -0.00053   -0.00298    0.00102 
O3    4    0.369970    0.288665   -0.185936    11.00000    0.01224    0.02124 = 
         0.01921   -0.00474    0.00098    0.00026 
H3    2    0.488373    0.308953   -0.108054    11.00000   -1.50000 
N2    3    0.238168    0.343272   -0.071567    11.00000    0.01368    0.01401 = 
         0.01696   -0.00044    0.00181   -0.00014 
H2A   2    0.257372    0.300547    0.045443    11.00000   -1.50000 
H2B   2    0.250675    0.450193   -0.057356    11.00000   -1.50000 
H2C   2    0.125986    0.314750   -0.139108    11.00000   -1.50000 
C1    1    0.755687    0.080554    0.065435    11.00000    0.02101    0.01283 = 
         0.02478   -0.00031    0.00128   -0.00044 
H1A   2    0.853932    0.015677    0.127347    11.00000   -1.50000 
H1B   2    0.729896    0.056953   -0.066117    11.00000   -1.50000 
H1C   2    0.648219    0.057953    0.117527    11.00000   -1.50000 
C2    1    0.803124    0.250538    0.092494    11.00000    0.01341    0.01389 = 
         0.01522    0.00008    0.00213    0.00051 
HKLF 4 
  
REM  p1 in P2(1)/c 
REM R1 =  0.0302 for     956 Fo > 4sig(Fo)  and  0.0338 for all    1067 data 
REM     76 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0503      0.0947 
  
REM Highest difference peak  0.194,  deepest hole -0.241,  1-sigma level  0.052 
Q1    1   0.5744  0.3170 -0.0005  11.00000  0.05    0.19 
Q2    1   1.0228  0.3417  0.1017  11.00000  0.05    0.17 
Q3    1   0.8367  0.0424 -0.0393  11.00000  0.05    0.16 
Q4    1   0.8816  0.2604  0.2216  11.00000  0.05    0.16 
Q5    1   0.7806  0.1642  0.0919  11.00000  0.05    0.16 
;
_shelx_res_checksum              99006
####################################################################### 
# 
# 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_NH3EtOH-OAc
_database_code_depnum_ccdc_archive 'CCDC 1559356'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H11 N O3'
_chemical_formula_weight         121.14

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6326(3)
_cell_length_b                   9.1273(3)
_cell_length_c                   9.7984(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.806(2)
_cell_angle_gamma                90
_cell_volume                     659.94(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      34.91

_exptl_crystal_description       Irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   'Bruker AXScale'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31946
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         34.981
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2896
_reflns_number_gt                2463
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0736P)²+0.0821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.16745(9) 0.34666(7) 0.62546(6) 0.03201(14) Uani 1 1 d . . . . .
H1C H 0.1450(19) 0.3268(14) 0.5302(15) 0.048 Uiso 1 1 d . U . . .
O2 O 0.36031(8) 0.15305(7) 0.38873(5) 0.02907(13) Uani 1 1 d . . . . .
O3 O 0.10688(7) 0.28383(6) 0.34850(5) 0.02507(12) Uani 1 1 d . . . . .
N1 N 0.13024(7) 0.53883(6) 0.84548(6) 0.01934(11) Uani 1 1 d . . . . .
H1D H 0.1467(15) 0.5793(13) 0.9337(12) 0.029 Uiso 1 1 d . U . . .
H1E H 0.0559(15) 0.4598(13) 0.8430(12) 0.029 Uiso 1 1 d . U . . .
H1F H 0.0639(15) 0.6006(13) 0.7819(12) 0.029 Uiso 1 1 d . U . . .
C1 C 0.30604(9) 0.50169(8) 0.81534(8) 0.02581(14) Uani 1 1 d . . . . .
H1A H 0.3564(15) 0.4168(13) 0.8699(12) 0.031 Uiso 1 1 d . U . . .
H1B H 0.3852(15) 0.5823(12) 0.8442(12) 0.031 Uiso 1 1 d . U . . .
C2 C 0.28033(10) 0.47059(8) 0.66031(8) 0.02662(14) Uani 1 1 d . . . . .
H2A H 0.2238(16) 0.5591(12) 0.6029(12) 0.032 Uiso 1 1 d . U . . .
H2B H 0.4005(15) 0.4485(13) 0.6448(12) 0.032 Uiso 1 1 d . U . . .
C3 C 0.23797(8) 0.22836(7) 0.30985(6) 0.01887(12) Uani 1 1 d . . . . .
C4 C 0.24839(11) 0.25768(11) 0.16008(7) 0.03288(18) Uani 1 1 d . . . . .
H4A H 0.3554(19) 0.2076(17) 0.1440(14) 0.049 Uiso 1 1 d . U . . .
H4B H 0.1407(18) 0.2279(17) 0.0971(15) 0.049 Uiso 1 1 d . U . . .
H4C H 0.2626(18) 0.3727(17) 0.1476(15) 0.049 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0449(3) 0.0323(3) 0.0221(2) -0.00665(18) 0.0144(2) -0.0099(2)
O2 0.0310(3) 0.0362(3) 0.0204(2) 0.00753(18) 0.00708(19) 0.0150(2)
O3 0.0217(2) 0.0355(3) 0.0182(2) 0.00081(16) 0.00554(16) 0.00752(17)
N1 0.0193(2) 0.0203(2) 0.0177(2) -0.00143(16) 0.00351(16) -0.00038(17)
C1 0.0192(3) 0.0281(3) 0.0288(3) -0.0060(2) 0.0038(2) 0.0030(2)
C2 0.0286(3) 0.0256(3) 0.0298(3) -0.0007(2) 0.0150(3) -0.0005(2)
C3 0.0193(2) 0.0217(3) 0.0150(2) -0.00004(17) 0.00326(18) 0.00110(18)
C4 0.0267(3) 0.0551(5) 0.0182(3) 0.0080(3) 0.0082(2) 0.0119(3)

_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 C2 1.4100(9) . ?
O2 C3 1.2542(7) . ?
O3 C3 1.2628(8) . ?
N1 C1 1.4850(9) . ?
C1 C2 1.5080(10) . ?
C3 C4 1.5136(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
N1 C1 C2 110.59(5) . . ?
O1 C2 C1 108.00(6) . . ?
O2 C3 O3 123.85(6) . . ?
O2 C3 C4 118.63(6) . . ?
O3 C3 C4 117.50(6) . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049

_shelx_res_file                  
; 
  
    s1.res created by SHELXL-2014/7 
  
TITL s1 in P2(1)/n 
CELL 0.71073   7.6326   9.1273   9.7984  90.000 104.806  90.000 
ZERR    4.00   0.0003   0.0003   0.0003   0.000   0.002   0.000 
LATT  1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 16 44 4 12 
TEMP -173.000 
SIZE 0.10 0.18 0.26 
  
L.S. 16 
ACTA 
FMAP 2 
PLAN 20 
OMIT -1 0 3 
WGHT    0.073600    0.082100 
FVAR       0.31591 
O1    4    0.167449    0.346661    0.625464    11.00000    0.04486    0.03232 = 
         0.02207   -0.00665    0.01442   -0.00985 
H1C   2    0.144959    0.326787    0.530197    11.00000   -1.50000 
O2    4    0.360307    0.153047    0.388735    11.00000    0.03096    0.03616 = 
         0.02037    0.00753    0.00708    0.01504 
O3    4    0.106880    0.283833    0.348500    11.00000    0.02173    0.03552 = 
         0.01821    0.00081    0.00554    0.00752 
N1    3    0.130243    0.538828    0.845475    11.00000    0.01931    0.02034 = 
         0.01770   -0.00143    0.00351   -0.00038 
H1D   2    0.146733    0.579266    0.933671    11.00000   -1.50000 
H1E   2    0.055878    0.459839    0.842991    11.00000   -1.50000 
H1F   2    0.063872    0.600557    0.781863    11.00000   -1.50000 
C1    1    0.306043    0.501688    0.815338    11.00000    0.01921    0.02809 = 
         0.02885   -0.00603    0.00381    0.00295 
H1A   2    0.356416    0.416808    0.869877    11.00000   -1.20000 
H1B   2    0.385211    0.582299    0.844152    11.00000   -1.20000 
C2    1    0.280333    0.470589    0.660310    11.00000    0.02856    0.02563 = 
         0.02982   -0.00070    0.01502   -0.00046 
H2A   2    0.223803    0.559136    0.602915    11.00000   -1.20000 
H2B   2    0.400542    0.448470    0.644829    11.00000   -1.20000 
C3    1    0.237974    0.228357    0.309845    11.00000    0.01930    0.02166 = 
         0.01505   -0.00004    0.00326    0.00110 
C4    1    0.248387    0.257681    0.160082    11.00000    0.02668    0.05509 = 
         0.01823    0.00802    0.00824    0.01192 
H4A   2    0.355426    0.207619    0.143983    11.00000   -1.50000 
H4B   2    0.140745    0.227855    0.097142    11.00000   -1.50000 
H4C   2    0.262592    0.372667    0.147619    11.00000   -1.50000 
  
HKLF 4 
  
REM  s1 in P2(1)/n 
REM R1 =  0.0390 for    2463 Fo > 4sig(Fo)  and  0.0458 for all    2896 data 
REM    106 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0714      0.0695 
  
REM Highest difference peak  0.415,  deepest hole -0.326,  1-sigma level  0.049 
Q1    1   0.2921  0.4948  0.7391  11.00000  0.05    0.41 
Q2    1   0.2466  0.2378  0.2402  11.00000  0.05    0.38 
Q3    1   0.2314  0.1798  0.1560  11.00000  0.05    0.38 
Q4    1   0.3060  0.1944  0.3549  11.00000  0.05    0.33 
Q5    1   0.1136  0.3961  0.5974  11.00000  0.05    0.29 
Q6    1   0.1647  0.2569  0.3235  11.00000  0.05    0.23 
Q7    1   0.1504  0.3251  0.6653  11.00000  0.05    0.23 
Q8    1   0.3621  0.1544  0.4374  11.00000  0.05    0.22 
Q9    1   0.1576  0.3329  0.3617  11.00000  0.05    0.21 
Q10   1   0.4107  0.1239  0.3547  11.00000  0.05    0.19 
Q11   1   0.1170  0.2588  0.3991  11.00000  0.05    0.18 
Q12   1   0.0671  0.3215  0.2871  11.00000  0.05    0.18 
Q13   1   0.2165  0.5215  0.8350  11.00000  0.05    0.16 
Q14   1   0.2254  0.4996  0.6106  11.00000  0.05    0.15 
Q15   1   0.2276  0.3952  0.6469  11.00000  0.05    0.13 
Q16   1   0.1406  0.5645  0.8974  11.00000  0.05    0.13 
Q17   1   0.1236  0.2858  0.0970  11.00000  0.05    0.13 
Q18   1   0.1036  0.5795  0.8053  11.00000  0.05    0.13 
Q19   1   0.3809  0.6276  0.7940  11.00000  0.05    0.12 
Q20   1   0.1957  0.3380  0.1187  11.00000  0.05    0.12 
;
_shelx_res_checksum              16507
####################################################################### 
# 
# 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_NH3EtOAc
_database_code_depnum_ccdc_archive 'CCDC 1569889'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_NH3EtOAc            
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: Light atom structure collected against Mo K-alpha, abs. structure not significant for this study
;
# Added during the CSD deposition process: Monday 21 August 2017 01:11 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Ethylammonium acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H8 N +, C2 H3 O2 -'
_chemical_formula_sum            'C4 H11 N O2'
_chemical_formula_weight         105.14

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   6.9335(6)
_cell_length_b                   6.9335(6)
_cell_length_c                   10.7367(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     446.99(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7272
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      32.90

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             174
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'Bruker AXScale'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15721
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         33.123
_diffrn_reflns_theta_full        25.242
_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 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2239
_reflns_number_gt                1956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.994

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0510P)²+0.0342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     78
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
N1 N 0.1234(2) 0.7255(2) 0.04752(12) 0.0154(3) Uani 1 1 d . . . . .
O1 O 0.3044(2) 0.46928(19) -0.02893(11) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.3148(2) 0.3135(2) 0.02664(14) 0.0130(3) Uani 1 1 d . . . . .
O2 O 0.3205(2) 0.15915(19) -0.03094(11) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.3279(3) 0.3195(3) 0.16766(16) 0.0176(3) Uani 1 1 d . . . . .
H4A H 0.2545 0.1669 0.2001 0.026 Uiso 1 1 calc R U . . .
H4B H 0.2532 0.3971 0.2005 0.026 Uiso 1 1 calc R U . . .
H4C H 0.4844 0.3982 0.1936 0.026 Uiso 1 1 calc R U . . .
C1 C -0.0980(3) 0.6348(3) -0.01317(15) 0.0196(3) Uani 1 1 d . . . . .
H1E H -0.1721 0.7160 0.0176 0.024 Uiso 1 1 calc R U . . .
H1D H -0.1925 0.4758 0.0092 0.024 Uiso 1 1 calc R U . . .
C2 C -0.0748(3) 0.6571(3) -0.15317(18) 0.0250(4) Uani 1 1 d . . . . .
H2A H 0.0245 0.8136 -0.1752 0.037 Uiso 1 1 calc R U . . .
H2B H -0.2215 0.6052 -0.1907 0.037 Uiso 1 1 calc R U . . .
H2C H -0.0123 0.5671 -0.1844 0.037 Uiso 1 1 calc R U . . .
H1A H 0.115(4) 0.720(5) 0.136(3) 0.034(7) Uiso 1 1 d . . . . .
H1B H 0.190(4) 0.656(4) 0.024(2) 0.023(5) Uiso 1 1 d . . . . .
H1C H 0.203(4) 0.861(4) 0.029(2) 0.025(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0208(6) 0.0146(6) 0.0134(6) -0.0002(5) -0.0004(5) 0.0109(5)
O1 0.0339(6) 0.0204(5) 0.0148(5) 0.0017(4) 0.0015(5) 0.0192(5)
C3 0.0113(6) 0.0128(6) 0.0139(7) 0.0003(5) 0.0009(5) 0.0054(5)
O2 0.0321(6) 0.0163(5) 0.0170(5) 0.0001(4) 0.0031(5) 0.0142(5)
C4 0.0219(7) 0.0207(7) 0.0118(6) -0.0007(5) -0.0008(5) 0.0119(6)
C1 0.0192(7) 0.0207(7) 0.0194(8) 0.0012(6) -0.0002(6) 0.0104(6)
C2 0.0310(8) 0.0286(9) 0.0173(8) -0.0050(6) -0.0071(7) 0.0165(7)

_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
N1 C1 1.487(2) . ?
O1 C3 1.2671(19) . ?
C3 O2 1.2534(18) . ?
C3 C4 1.516(2) . ?
C1 C2 1.512(3) . ?

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
O2 C3 O1 122.34(15) . . ?
O2 C3 C4 119.26(13) . . ?
O1 C3 C4 118.37(13) . . ?
N1 C1 C2 110.95(13) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.064

_shelx_res_file                  
; 
  
    s1.res created by SHELXL-2014/7 
  
  
TITL s1 in P3(2) 
CELL 0.71073   6.93345   6.93345  10.73670  90.0000  90.0000 120.0000 
ZERR    3.00   0.00060   0.00060   0.00110   0.0000   0.0000   0.0000 
LATT -1 
SYMM -Y, X-Y, 0.66667+Z 
SYMM -X+Y, -X, 0.33333+Z 
SFAC C H N O 
UNIT 12 33 3 6 
TEMP -173 
SIZE 0.15 0.21 1.00 
  
L.S. 10 
ACTA 
FMAP 2 
PLAN 20 
  
WGHT    0.051000    0.034200 
FVAR       0.50056 
N1    3    0.123436    0.725519    0.047516    11.00000    0.02078    0.01463 = 
         0.01341   -0.00016   -0.00043    0.01086 
O1    4    0.304411    0.469279   -0.028934    11.00000    0.03390    0.02038 = 
         0.01481    0.00169    0.00146    0.01919 
C3    1    0.314831    0.313514    0.026636    11.00000    0.01133    0.01281 = 
         0.01386    0.00032    0.00094    0.00535 
O2    4    0.320470    0.159152   -0.030936    11.00000    0.03206    0.01627 = 
         0.01695    0.00005    0.00312    0.01422 
C4    1    0.327873    0.319454    0.167665    11.00000    0.02192    0.02073 = 
         0.01179   -0.00072   -0.00080    0.01187 
AFIX 137 
H4A   2    0.254484    0.166902    0.200054    11.00000   -1.50000 
H4B   2    0.253214    0.397077    0.200487    11.00000   -1.50000 
H4C   2    0.484352    0.398222    0.193606    11.00000   -1.50000 
AFIX   0 
C1    1   -0.098026    0.634800   -0.013165    11.00000    0.01922    0.02072 = 
         0.01942    0.00120   -0.00024    0.01043 
AFIX  23 
H1E   2   -0.172146    0.716037    0.017624    11.00000   -1.20000 
H1D   2   -0.192512    0.475802    0.009232    11.00000   -1.20000 
AFIX   0 
C2    1   -0.074759    0.657137   -0.153172    11.00000    0.03103    0.02865 = 
         0.01731   -0.00504   -0.00705    0.01650 
AFIX 137 
H2A   2    0.024544    0.813648   -0.175197    11.00000   -1.50000 
H2B   2   -0.221466    0.605161   -0.190709    11.00000   -1.50000 
H2C   2   -0.012270    0.567083   -0.184384    11.00000   -1.50000 
AFIX   0 
H1A   2    0.114634    0.719971    0.135722    11.00000    0.03430 
H1B   2    0.189533    0.656283    0.023833    11.00000    0.02304 
H1C   2    0.203106    0.860980    0.029492    11.00000    0.02488 
  
HKLF 4 
  
REM  s1 in P3(2) 
REM R1 =  0.0425 for    1956 Fo > 4sig(Fo)  and  0.0553 for all    2239 data 
REM     78 parameters refined using      1 restraints 
  
END 
  
WGHT      0.0443      0.0335 
  
REM Highest difference peak  0.226,  deepest hole -0.341,  1-sigma level  0.064 
Q1    1   0.3256  0.3154  0.0989  11.00000  0.05    0.23 
Q2    1  -0.0879  0.6497 -0.0832  11.00000  0.05    0.22 
Q3    1   0.1597  0.9257  0.1927  11.00000  0.05    0.17 
Q4    1   0.0095  0.0126  0.2361  11.00000  0.05    0.17 
Q5    1  -0.3197  0.6858 -0.2369  11.00000  0.05    0.17 
Q6    1   0.3133  0.4741 -0.0980  11.00000  0.05    0.17 
Q7    1   0.6943  0.6626  0.1671  11.00000  0.05    0.17 
Q8    1   0.3739  0.6550  0.0534  11.00000  0.05    0.16 
Q9    1  -0.1736  0.7109 -0.1833  11.00000  0.05    0.16 
Q10   1   0.2953  0.6863  0.1252  11.00000  0.05    0.15 
Q11   1   0.3399  0.1790 -0.1082  11.00000  0.05    0.15 
Q12   1  -0.2709  0.3314 -0.0605  11.00000  0.05    0.15 
Q13   1  -0.0136  0.9953 -0.1526  11.00000  0.05    0.15 
Q14   1   0.3170  0.6595 -0.1167  11.00000  0.05    0.15 
Q15   1   0.2324  0.1303 -0.1133  11.00000  0.05    0.15 
Q16   1  -0.3727  0.6430  0.0545  11.00000  0.05    0.15 
Q17   1   0.6192  0.3235  0.1086  11.00000  0.05    0.15 
Q18   1  -0.2238  0.7723 -0.0519  11.00000  0.05    0.15 
Q19   1  -0.0134  0.9882 -0.0127  11.00000  0.05    0.15 
Q20   1   0.3200  0.6047 -0.0451  11.00000  0.05    0.14 
;
_shelx_res_checksum              49811

#END
_exptl_crystal_recrystallization_method 
'Crystallized spontaneously from reaction mixture'
_chemical_properties_physical    Deliquescent
####################################################################### 
# 
# 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_ChoOAc
_database_code_depnum_ccdc_archive 'CCDC 1559357'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H17 N O3'
_chemical_formula_weight         163.21

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                   7.7116(4)
_cell_length_b                   7.1277(4)
_cell_length_c                   8.4076(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.612(2)
_cell_angle_gamma                90
_cell_volume                     450.98(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6074
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      33.12

_exptl_crystal_description       shard
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6206
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'Bruker AXScale'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11571
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         33.177
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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             3417
_reflns_number_gt                3264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0506P)²+0.0114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1459 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.48022(10) 0.19148(12) 0.88172(13) 0.0305(2) Uani 1 1 d . . . . .
H1C H 0.541(3) 0.115(4) 0.843(3) 0.046 Uiso 1 1 d . U . . .
O2 O 0.70635(10) -0.03535(12) 0.78084(11) 0.02549(16) Uani 1 1 d . . . . .
O3 O 0.83680(11) -0.25847(13) 0.66505(11) 0.02900(18) Uani 1 1 d . . . . .
N1 N 0.06775(10) 0.29612(11) 0.76210(9) 0.01519(13) Uani 1 1 d . . . . .
C5 C 0.18709(13) 0.46085(15) 0.75765(13) 0.02205(18) Uani 1 1 d . . . . .
H5A H 0.116(3) 0.563(3) 0.743(2) 0.033 Uiso 1 1 d . U . . .
H5B H 0.239(3) 0.440(3) 0.663(2) 0.033 Uiso 1 1 d . U . . .
H5C H 0.275(3) 0.458(3) 0.854(2) 0.033 Uiso 1 1 d . U . . .
C4 C -0.02157(13) 0.31714(15) 0.90242(11) 0.01977(17) Uani 1 1 d . . . . .
H4A H -0.090(2) 0.426(3) 0.885(2) 0.030 Uiso 1 1 d . U . . .
H4B H 0.069(2) 0.328(3) 0.999(2) 0.030 Uiso 1 1 d . U . . .
H4C H -0.100(3) 0.213(3) 0.899(2) 0.030 Uiso 1 1 d . U . . .
C3 C -0.07449(12) 0.29397(16) 0.60814(11) 0.02068(17) Uani 1 1 d . . . . .
H3A H -0.141(3) 0.409(3) 0.603(2) 0.031 Uiso 1 1 d . U . . .
H3B H -0.154(3) 0.194(3) 0.617(2) 0.031 Uiso 1 1 d . U . . .
H3C H -0.021(3) 0.286(3) 0.522(2) 0.031 Uiso 1 1 d . U . . .
C1 C 0.16792(12) 0.11220(13) 0.77137(11) 0.01740(16) Uani 1 1 d . . . . .
H1A H 0.206(2) 0.097(2) 0.6664(19) 0.021 Uiso 1 1 d . U . . .
H1B H 0.084(2) 0.017(2) 0.773(2) 0.021 Uiso 1 1 d . U . . .
C2 C 0.33022(13) 0.09568(16) 0.91144(12) 0.02240(18) Uani 1 1 d . . . . .
H2A H 0.307(3) 0.144(3) 1.009(2) 0.027 Uiso 1 1 d . U . . .
H2B H 0.353(2) -0.037(3) 0.924(2) 0.027 Uiso 1 1 d . U . . .
C7 C 0.70230(12) -0.17862(13) 0.69258(11) 0.01752(16) Uani 1 1 d . . . . .
C6 C 0.52282(16) -0.2629(2) 0.61728(18) 0.0362(3) Uani 1 1 d . . . . .
H6C H 0.511(4) -0.267(4) 0.493(3) 0.054 Uiso 1 1 d . U . . .
H6B H 0.430(4) -0.203(4) 0.646(3) 0.054 Uiso 1 1 d . U . . .
H6A H 0.521(3) -0.392(4) 0.670(3) 0.054 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0161(3) 0.0246(4) 0.0498(5) -0.0092(3) 0.0050(3) 0.0007(3)
O2 0.0200(3) 0.0237(3) 0.0331(4) -0.0061(3) 0.0064(3) -0.0011(3)
O3 0.0214(3) 0.0304(4) 0.0370(4) -0.0036(3) 0.0104(3) 0.0037(3)
N1 0.0136(3) 0.0160(3) 0.0156(3) -0.0005(2) 0.0025(2) -0.0011(2)
C5 0.0180(4) 0.0168(4) 0.0306(5) 0.0017(3) 0.0035(3) -0.0033(3)
C4 0.0186(4) 0.0242(4) 0.0173(3) -0.0022(3) 0.0056(3) 0.0023(3)
C3 0.0183(4) 0.0256(4) 0.0163(3) 0.0008(3) -0.0004(3) -0.0009(3)
C1 0.0175(3) 0.0154(3) 0.0195(4) -0.0021(3) 0.0044(3) 0.0003(3)
C2 0.0185(4) 0.0237(4) 0.0239(4) -0.0013(3) 0.0021(3) 0.0041(3)
C7 0.0154(3) 0.0193(4) 0.0178(3) 0.0029(3) 0.0034(3) -0.0006(3)
C6 0.0207(5) 0.0454(7) 0.0406(7) -0.0131(5) 0.0027(4) -0.0092(5)

_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 C2 1.4117(14) . ?
O2 C7 1.2586(12) . ?
O3 C7 1.2483(11) . ?
N1 C5 1.4974(12) . ?
N1 C4 1.4978(12) . ?
N1 C3 1.5030(11) . ?
N1 C1 1.5149(12) . ?
C1 C2 1.5243(13) . ?
C7 C6 1.5147(15) . ?

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
C5 N1 C4 109.39(8) . . ?
C5 N1 C3 108.87(7) . . ?
C4 N1 C3 107.74(7) . . ?
C5 N1 C1 111.75(7) . . ?
C4 N1 C1 111.29(7) . . ?
C3 N1 C1 107.67(7) . . ?
N1 C1 C2 115.47(7) . . ?
O1 C2 C1 113.09(9) . . ?
O3 C7 O2 124.37(9) . . ?
O3 C7 C6 117.53(9) . . ?
O2 C7 C6 118.09(9) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035

_shelx_res_file                  
; 
  
    p2.res created by SHELXL-2014/7 
  
  
TITL p2 in P2(1) 
CELL 0.71073   7.7116   7.1277   8.4076  90.000 102.612  90.000 
ZERR    2.00   0.0004   0.0004   0.0005   0.000   0.002   0.000 
LATT -1 
SYMM -X, 0.5+Y, -Z 
SFAC C  H  N  O 
UNIT 14  34  2  6 
L.S. 20 
ACTA 
BOND 
FMAP 2 
PLAN 5 
SIZE 0.01 0.02 0.12 
TEMP -173.000 
  
WGHT    0.050600    0.011400 
FVAR       0.67517 
O1    4    0.480215    0.191477    0.881715    11.00000    0.01608    0.02461 = 
         0.04984   -0.00916    0.00496    0.00070 
H1C   2    0.541319    0.114626    0.843472    11.00000   -1.50000 
O2    4    0.706352   -0.035353    0.780837    11.00000    0.01998    0.02365 = 
         0.03313   -0.00610    0.00640   -0.00108 
O3    4    0.836798   -0.258468    0.665047    11.00000    0.02144    0.03042 = 
         0.03698   -0.00360    0.01036    0.00373 
N1    3    0.067755    0.296116    0.762104    11.00000    0.01362    0.01599 = 
         0.01564   -0.00046    0.00247   -0.00110 
C5    1    0.187090    0.460853    0.757653    11.00000    0.01797    0.01680 = 
         0.03057    0.00172    0.00352   -0.00330 
H5A   2    0.116121    0.563161    0.742606    11.00000   -1.50000 
H5B   2    0.239418    0.439580    0.663273    11.00000   -1.50000 
H5C   2    0.275384    0.458034    0.853554    11.00000   -1.50000 
C4    1   -0.021566    0.317142    0.902419    11.00000    0.01859    0.02419 = 
         0.01730   -0.00225    0.00564    0.00231 
H4A   2   -0.090391    0.425899    0.884654    11.00000   -1.50000 
H4B   2    0.069378    0.327993    0.998651    11.00000   -1.50000 
H4C   2   -0.100163    0.213139    0.898635    11.00000   -1.50000 
C3    1   -0.074492    0.293972    0.608142    11.00000    0.01826    0.02560 = 
         0.01627    0.00077   -0.00041   -0.00090 
H3A   2   -0.140752    0.408903    0.603260    11.00000   -1.50000 
H3B   2   -0.153536    0.194492    0.616668    11.00000   -1.50000 
H3C   2   -0.021390    0.285730    0.521909    11.00000   -1.50000 
C1    1    0.167917    0.112203    0.771370    11.00000    0.01753    0.01536 = 
         0.01948   -0.00213    0.00443    0.00028 
H1A   2    0.206319    0.097210    0.666394    11.00000   -1.20000 
H1B   2    0.083925    0.017148    0.773282    11.00000   -1.20000 
C2    1    0.330216    0.095681    0.911445    11.00000    0.01849    0.02366 = 
         0.02391   -0.00127    0.00213    0.00407 
H2A   2    0.307446    0.143551    1.008510    11.00000   -1.20000 
H2B   2    0.352557   -0.037013    0.924244    11.00000   -1.20000 
C7    1    0.702295   -0.178617    0.692580    11.00000    0.01537    0.01931 = 
         0.01777    0.00293    0.00338   -0.00064 
C6    1    0.522823   -0.262863    0.617280    11.00000    0.02072    0.04540 = 
         0.04059   -0.01313    0.00266   -0.00919 
H6C   2    0.511233   -0.267426    0.492915    11.00000   -1.50000 
H6B   2    0.430007   -0.202823    0.645530    11.00000   -1.50000 
H6A   2    0.521202   -0.392407    0.670336    11.00000   -1.50000 
HKLF 4 
  
REM  p2 in P2(1) 
REM R1 =  0.0290 for    3264 Fo > 4sig(Fo)  and  0.0306 for all    3417 data 
REM    151 parameters refined using      1 restraints 
  
END 
  
WGHT      0.0512      0.0127 
  
REM Highest difference peak  0.312,  deepest hole -0.147,  1-sigma level  0.035 
Q1    1   0.2471  0.1007  0.8450  11.00000  0.05    0.31 
Q2    1   0.0046  0.2916  0.6850  11.00000  0.05    0.26 
Q3    1   0.6178 -0.2203  0.6526  11.00000  0.05    0.26 
Q4    1   0.1215  0.2068  0.7621  11.00000  0.05    0.23 
Q5    1   0.7810 -0.1963  0.6710  11.00000  0.05    0.21 
;
_shelx_res_checksum              33400
####################################################################### 
# 
# 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_NMe4OAc
_database_code_depnum_ccdc_archive 'CCDC 1569888'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_NMe4OAc             
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Structure determined from crude crystal intergrown with other phase, see ESI
;
_vrf_PLAT242_NMe4OAc             
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
RESPONSE: Reasonable for central nitrogen bonded to four terminal methyl groups
;
_vrf_PLAT340_NMe4OAc             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
RESPONSE: Related to poor quality of crystal as mentioned in reference
;
_vrf_PLAT911_NMe4OAc             
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report
RESPONSE: These are specific low angle reflections which are buried by background scattering
;
_vrf_PLAT978_NMe4OAc             
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info
RESPONSE: The aformentioned quality issues limit this refinement to the low resolution data.
;
# Added during the CSD deposition process: Monday 21 August 2017 01:11 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H15 N O2'
_chemical_formula_weight         133.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_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'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   10.9186(7)
_cell_length_b                   10.9186(7)
_cell_length_c                   13.3235(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1588.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3529
_cell_measurement_theta_min      5.24
_cell_measurement_theta_max      74.24

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.670
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4559
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            8487
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_av_R_equivalents  0.1290
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.237
_diffrn_reflns_theta_max         74.369
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1605
_reflns_number_gt                1352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.977

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
'Structure determined from crude crystal obtained from starting material with numerous data quality issues.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1087P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 480 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1605
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
N2 N 0.5000 0.5000 0.7985(2) 0.0168(8) Uani 1 2 d S T P . .
N1 N 1.0000 0.5000 0.7714(3) 0.0210(8) Uani 1 2 d S T P . .
O1 O 0.3774(2) 0.2239(3) 0.94001(18) 0.0428(8) Uani 1 1 d . . . . .
O2 O 0.2210(3) 0.1939(3) 0.83626(17) 0.0452(8) Uani 1 1 d . . . . .
C4 C 0.4304(3) 0.4141(3) 0.7331(2) 0.0261(7) Uani 1 1 d . . . . .
H4A H 0.3734 0.4606 0.6909 0.039 Uiso 1 1 calc R U . . .
H4B H 0.3843 0.3565 0.7750 0.039 Uiso 1 1 calc R U . . .
H4C H 0.4876 0.3687 0.6904 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4134(3) 0.5714(3) 0.8632(2) 0.0265(7) Uani 1 1 d . . . . .
H3A H 0.3556 0.6163 0.8206 0.040 Uiso 1 1 calc R U . . .
H3B H 0.4598 0.6295 0.9044 0.040 Uiso 1 1 calc R U . . .
H3C H 0.3682 0.5151 0.9069 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2657(3) 0.2142(3) 0.9208(2) 0.0214(7) Uani 1 1 d . . . . .
C2 C 1.0796(3) 0.4230(3) 0.7062(3) 0.0354(9) Uani 1 1 d . . . . .
H2A H 1.1340 0.4758 0.6669 0.053 Uiso 1 1 calc R U . . .
H2B H 1.0284 0.3744 0.6608 0.053 Uiso 1 1 calc R U . . .
H2C H 1.1288 0.3680 0.7482 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1788(4) 0.2329(6) 1.0066(3) 0.0544(13) Uani 1 1 d . . . . .
H6A H 0.1587 0.3201 1.0123 0.082 Uiso 1 1 calc R U . . .
H6B H 0.2172 0.2049 1.0690 0.082 Uiso 1 1 calc R U . . .
H6C H 0.1038 0.1859 0.9945 0.082 Uiso 1 1 calc R U . . .
C1 C 1.0780(3) 0.5808(4) 0.8355(3) 0.0396(9) Uani 1 1 d . . . . .
H1A H 1.0255 0.6347 0.8756 0.059 Uiso 1 1 calc R U . . .
H1B H 1.1314 0.6306 0.7926 0.059 Uiso 1 1 calc R U . . .
H1C H 1.1282 0.5302 0.8801 0.059 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0146(15) 0.0227(17) 0.0132(15) 0.000 0.000 0.0004(15)
N1 0.0173(16) 0.0234(17) 0.0224(16) 0.000 0.000 -0.0031(12)
O1 0.0290(13) 0.0661(19) 0.0333(12) 0.0006(12) 0.0040(10) -0.0070(12)
O2 0.0494(16) 0.0667(19) 0.0194(11) -0.0118(11) -0.0031(11) -0.0115(14)
C4 0.0289(16) 0.0282(16) 0.0212(13) -0.0025(12) -0.0045(12) -0.0107(14)
C3 0.0236(14) 0.0365(17) 0.0195(14) -0.0038(12) 0.0028(11) 0.0088(14)
C5 0.0300(16) 0.0193(13) 0.0148(13) 0.0012(10) 0.0025(11) -0.0032(11)
C2 0.0265(16) 0.0288(17) 0.051(2) -0.0069(15) 0.0068(15) 0.0053(14)
C6 0.0337(18) 0.109(4) 0.0202(16) 0.001(2) 0.0048(14) 0.014(2)
C1 0.0344(18) 0.052(2) 0.0320(17) -0.0115(16) -0.0008(14) -0.0221(17)

_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
N2 C4 1.488(3) 2_665 ?
N2 C4 1.489(3) . ?
N2 C3 1.498(4) . ?
N2 C3 1.498(4) 2_665 ?
N1 C2 1.488(4) 2_765 ?
N1 C2 1.488(4) . ?
N1 C1 1.494(4) . ?
N1 C1 1.494(4) 2_765 ?
O1 C5 1.250(4) . ?
O2 C5 1.248(4) . ?
C5 C6 1.499(4) . ?

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
C4 N2 C4 108.4(3) 2_665 . ?
C4 N2 C3 109.34(18) 2_665 . ?
C4 N2 C3 110.02(18) . . ?
C4 N2 C3 110.02(18) 2_665 2_665 ?
C4 N2 C3 109.34(18) . 2_665 ?
C3 N2 C3 109.7(3) . 2_665 ?
C2 N1 C2 108.7(4) 2_765 . ?
C2 N1 C1 109.4(2) 2_765 . ?
C2 N1 C1 109.5(2) . . ?
C2 N1 C1 109.5(2) 2_765 2_765 ?
C2 N1 C1 109.4(2) . 2_765 ?
C1 N1 C1 110.3(4) . 2_765 ?
O2 C5 O1 125.5(3) . . ?
O2 C5 C6 117.7(3) . . ?
O1 C5 C6 116.7(3) . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.109

_shelx_res_file                  
; 
  
    s1.res created by SHELXL-2014/7 
  
  
TITL s1 in P-42(1)c 
CELL 1.54178  10.9186  10.9186  13.3235  90.0000  90.0000  90.0000 
ZERR    8.00   0.0007   0.0007   0.0011   0.0000   0.0000   0.0000 
LATT -1 
SYMM -X, -Y, Z 
SYMM Y, -X, -Z 
SYMM -Y, X, -Z 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SYMM 0.5+X, 0.5-Y, 0.5-Z 
SYMM 0.5-Y, 0.5-X, 0.5+Z 
SYMM 0.5+Y, 0.5+X, 0.5+Z 
SFAC C H N O 
UNIT 48 120 8 16 
TEMP -100 
L.S. 16 
acta 
FMAP 2 
PLAN 20 
  
WGHT    0.108700 
FVAR       0.20355 
N2    3    0.500000    0.500000    0.798516    10.50000    0.01457    0.02271 = 
         0.01325    0.00000    0.00000    0.00040 
N1    3    1.000000    0.500000    0.771371    10.50000    0.01729    0.02343 = 
         0.02243    0.00000    0.00000   -0.00311 
O1    4    0.377391    0.223927    0.940007    11.00000    0.02897    0.06614 = 
         0.03334    0.00062    0.00400   -0.00698 
O2    4    0.221046    0.193888    0.836259    11.00000    0.04942    0.06669 = 
         0.01939   -0.01177   -0.00314   -0.01150 
C4    1    0.430379    0.414132    0.733131    11.00000    0.02886    0.02820 = 
         0.02117   -0.00246   -0.00455   -0.01075 
AFIX 137 
H4A   2    0.373439    0.460638    0.690936    11.00000   -1.50000 
H4B   2    0.384276    0.356524    0.775012    11.00000   -1.50000 
H4C   2    0.487587    0.368701    0.690396    11.00000   -1.50000 
AFIX   0 
C3    1    0.413449    0.571392    0.863210    11.00000    0.02357    0.03647 = 
         0.01946   -0.00381    0.00279    0.00879 
AFIX 137 
H3A   2    0.355647    0.616273    0.820623    11.00000   -1.50000 
H3B   2    0.459824    0.629507    0.904415    11.00000   -1.50000 
H3C   2    0.368249    0.515107    0.906920    11.00000   -1.50000 
AFIX   0 
C5    1    0.265737    0.214241    0.920813    11.00000    0.02997    0.01933 = 
         0.01476    0.00118    0.00253   -0.00324 
C2    1    1.079600    0.422983    0.706248    11.00000    0.02646    0.02878 = 
         0.05103   -0.00691    0.00677    0.00526 
AFIX 137 
H2A   2    1.134011    0.475805    0.666901    11.00000   -1.50000 
H2B   2    1.028440    0.374407    0.660774    11.00000   -1.50000 
H2C   2    1.128758    0.368028    0.748189    11.00000   -1.50000 
AFIX   0 
C6    1    0.178832    0.232874    1.006560    11.00000    0.03374    0.10912 = 
         0.02020    0.00123    0.00483    0.01418 
AFIX 137 
H6A   2    0.158653    0.320053    1.012272    11.00000   -1.50000 
H6B   2    0.217235    0.204872    1.068955    11.00000   -1.50000 
H6C   2    0.103790    0.185878    0.994511    11.00000   -1.50000 
AFIX   0 
C1    1    1.077996    0.580810    0.835454    11.00000    0.03445    0.05246 = 
         0.03196   -0.01149   -0.00076   -0.02211 
AFIX 137 
H1A   2    1.025537    0.634651    0.875645    11.00000   -1.50000 
H1B   2    1.131366    0.630554    0.792612    11.00000   -1.50000 
H1C   2    1.128238    0.530223    0.880136    11.00000   -1.50000 
AFIX   0 
HKLF 4 
  
REM  s1 in P-42(1)c 
REM R1 =  0.0694 for    1352 Fo > 4sig(Fo)  and  0.0815 for all    1605 data 
REM     88 parameters refined using      0 restraints 
  
END 
  
WGHT      0.1054      0.0000 
  
REM Highest difference peak  0.371,  deepest hole -0.388,  1-sigma level  0.109 
Q1    1   0.0894  0.2594  0.9990  11.00000  0.05    0.37 
Q2    1   0.4419  0.7235  0.8655  11.00000  0.05    0.30 
Q3    1   0.4822  0.7602  0.8961  11.00000  0.05    0.30 
Q4    1   1.1363  0.3672  0.6894  11.00000  0.05    0.30 
Q5    1   0.4688  0.2438  0.7175  11.00000  0.05    0.29 
Q6    1   0.3507  0.1334  0.9301  11.00000  0.05    0.28 
Q7    1   0.2731  0.4286  0.9299  11.00000  0.05    0.27 
Q8    1   0.2994  0.5718  0.8763  11.00000  0.05    0.26 
Q9    1   1.0126  0.7165  0.8383  11.00000  0.05    0.26 
Q10   1   1.1571  0.4205  0.6428  11.00000  0.05    0.24 
Q11   1   1.0499  0.5856  0.9187  11.00000  0.05    0.23 
Q12   1   0.4147  0.2233  0.9535  11.00000  0.05    0.23 
Q13   1   0.2329  0.1067  1.0253  11.00000  0.05    0.23 
Q14   1   0.3001  0.4396  0.7560  11.00000  0.05    0.22 
Q15   1   1.0422  0.7609  0.9271  11.00000  0.05    0.22 
Q16   1   0.4059  0.2683  1.0194  11.00000  0.05    0.22 
Q17   1   1.2247  0.4583  0.8935  11.00000  0.05    0.22 
Q18   1   0.4657  0.1602  0.9251  11.00000  0.05    0.21 
Q19   1   0.2771  0.5422  0.6626  11.00000  0.05    0.21 
Q20   1   0.4717  0.2755  0.9254  11.00000  0.05    0.20 
;
_shelx_res_checksum              69914
_chemical_properties_physical    Deliquescent
