#------------------------------------------------------------------------------
#$Date: 2017-12-23 04:23:10 +0200 (Sat, 23 Dec 2017) $
#$Revision: 204501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548543.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1548543
loop_
_publ_author_name
'Zeng, Qingying'
'Mukherjee, Arijit'
'M\"uller, Peter'
'Rogers, Robin D.'
'Myerson, Allan S.'
_publ_section_title
;
 Exploring the role of ionic liquids to tune the polymorphic outcome of
 organic compounds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C7SC04353H
_journal_year                    2018
_chemical_formula_sum            'C14 H18 N2 O4'
_chemical_formula_weight         278.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-03 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                77.801(7)
_cell_angle_beta                 83.650(8)
_cell_angle_gamma                88.409(7)
_cell_formula_units_Z            1
_cell_length_a                   6.746(3)
_cell_length_b                   7.246(3)
_cell_length_c                   7.434(3)
_cell_measurement_reflns_used    8839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.28
_cell_measurement_theta_min      2.82
_cell_volume                     353.0(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2771
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.642
_diffrn_reflns_theta_min         2.820
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.746552
_exptl_absorpt_correction_T_min  0.290833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1369P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2101
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04353h2.cif
_cod_data_source_block           X17067
_cod_original_cell_volume        353.0(2)
_cod_database_code               1548543
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_file
; 
  
    X17067.res created by SHELXL-2014/7 
  
  
TITL X17067 in P-1 
CELL 0.71073   6.74570   7.24630   7.43410  77.8007  83.6503  88.4090 
ZERR    1.00   0.00250   0.00260   0.00270   0.0073   0.0076   0.0073 
LATT  1 
SFAC C H N O 
UNIT 14 18 2 4 
LIST 4 
TEMP -173 
SIZE 0.113 0.22 0.409 
  
OMIT   0   6   3   ! outlier, Fo > Fc 
  
ACTA 
WPDB -2 
  
L.S. 100 
BOND $H 
FMAP 2 
PLAN 20 
MERG 0 
  
HTAB 
EQIV $1 -x+1, -y+1, -z+1 
HTAB O1 O1_$1 
  
SIMU 
RIGU 
  
DFIX 0.84 O1 H1 
  
WGHT    0.136900 
BASF   0.07582 
FVAR       1.09079 
O1    4    0.515805    0.658153    0.400509    11.00000    0.02579    0.01746 = 
         0.03315    0.00724    0.00038   -0.00032 
H1    2    0.511702    0.546408    0.463940    10.50000   -1.50000 
REM Q1    1   0.5058  0.5496  0.4665  11.00000  0.05    0.47 
O2    4    0.810107    0.563289    0.283447    11.00000    0.04689    0.01732 = 
         0.05103    0.00725    0.01918    0.01054 
C1    1    0.681451    0.682894    0.297057    11.00000    0.02778    0.01348 = 
         0.02177   -0.00014   -0.00153   -0.00074 
C2    1    0.711706    0.875379    0.189789    11.00000    0.02265    0.01492 = 
         0.02183   -0.00048   -0.00119    0.00005 
C3    1    0.737381    1.034522    0.105486    11.00000    0.02138    0.01409 = 
         0.02264   -0.00016   -0.00255    0.00047 
C4    1    0.767277    1.227805    0.004156    11.00000    0.02684    0.01376 = 
         0.02916    0.00333   -0.00367   -0.00180 
AFIX 137 
H4A   2    0.898441    1.238897   -0.068413    11.00000   -1.50000 
H4B   2    0.760373    1.312374    0.091602    11.00000   -1.50000 
H4C   2    0.663206    1.262668   -0.079150    11.00000   -1.50000 
AFIX   0 
part -1 
REM  sadi n1 c1s n2 c5s 
REM  sadi n1 c2s n1 c4s n2 c3s n2 c4s 
REM  sadi c2s c1s c4s c1s c3s c5s c4s c5s 
N1S   3    1.128906    0.159434    0.362704    10.50000    0.02475    0.01170 = 
         0.02044   -0.00025   -0.00172    0.00151 
N2S   3    0.925709   -0.034515    0.548533    10.50000    0.02275    0.01064 = 
         0.01763   -0.00158   -0.00189    0.00238 
C1S   1    1.216068    0.332540    0.242351    10.50000    0.04238    0.01428 = 
         0.02733    0.00607    0.00306   -0.00432 
AFIX 137 
H1SA  2    1.358795    0.336536    0.255328    10.50000   -1.50000 
H1SB  2    1.149555    0.443214    0.278374    10.50000   -1.50000 
H1SC  2    1.197840    0.333032    0.113283    10.50000   -1.50000 
AFIX   0 
C2S   1    1.218102   -0.015663    0.387708    10.50000    0.02586    0.01322 = 
         0.02422   -0.00171   -0.00037    0.00489 
AFIX  43 
H2S   2    1.346573   -0.044919    0.334374    10.50000   -1.20000 
AFIX   0 
C3S   1    1.088302   -0.139933    0.503242    10.50000    0.02714    0.01424 = 
         0.02230   -0.00554   -0.00382    0.00873 
AFIX  43 
H3S   2    1.106832   -0.272027    0.543813    10.50000   -1.20000 
AFIX   0 
C4S   1    0.951212    0.141972    0.461481    10.50000    0.02932    0.01206 = 
         0.01955   -0.00450   -0.00299    0.00445 
AFIX  43 
H4S   2    0.857627    0.241376    0.468014    10.50000   -1.20000 
AFIX   0 
C5S   1    0.739648   -0.104960    0.664944    10.50000    0.02482    0.01361 = 
         0.02584   -0.00177    0.00139    0.00195 
AFIX  23 
H5SA  2    0.629392   -0.095904    0.585935    10.50000   -1.20000 
H5SB  2    0.704838   -0.024714    0.756434    10.50000   -1.20000 
AFIX   0 
C6S   1    0.761871   -0.306363    0.764923    10.50000    0.02665    0.01631 = 
         0.03003    0.00441   -0.00654   -0.00382 
AFIX 137 
H6SA  2    0.786632   -0.387391    0.674555    10.50000   -1.50000 
H6SB  2    0.639233   -0.346528    0.845860    10.50000   -1.50000 
H6SC  2    0.874240   -0.316495    0.839544    10.50000   -1.50000 
  
AFIX   0 
HKLF 5 
  
REM  X17067 in P-1 
REM R1 =  0.0624 for    2101 Fo > 4sig(Fo)  and  0.0790 for all    2771 data 
REM    134 parameters refined using    163 restraints 
  
END 
  
WGHT      0.1373      0.0000 
  
REM Instructions for potential hydrogen bonds 
HTAB O1 O1_$1 
HTAB C1S O2 
EQIV $2 x+1, y-1, z 
HTAB C2S O1_$2 
EQIV $3 -x+2, -y, -z+1 
HTAB C3S O2_$3 
HTAB C4S O2 
EQIV $4 x, y-1, z 
HTAB C5S O1_$4 
  
REM Highest difference peak  0.450,  deepest hole -0.319,  1-sigma level  0.075 
Q1    1   0.6685  0.9760  0.1780  11.00000  0.05    0.45 
Q2    1   0.7695  0.9361  0.1276  11.00000  0.05    0.43 
Q3    1   1.1643  0.0719  0.3854  11.00000  0.05    0.40 
Q4    1   0.5772  0.6711  0.3185  11.00000  0.05    0.39 
Q5    1   0.6110  0.6742  0.3751  11.00000  0.05    0.35 
Q6    1   0.8673  0.5939  0.1975  11.00000  0.05    0.32 
Q7    1   1.1415 -0.0716  0.4704  11.00000  0.05    0.32 
Q8    1   0.7111  0.7759  0.2472  11.00000  0.05    0.31 
Q9    1   0.7292  1.2530 -0.1239  11.00000  0.05    0.29 
Q10   1   0.7234  0.4992  0.3480  11.00000  0.05    0.29 
Q11   1   1.1898  0.2147  0.2969  11.00000  0.05    0.28 
Q12   1   1.1324 -0.0927  0.4016  11.00000  0.05    0.26 
Q13   1   0.7428  0.6328  0.2841  11.00000  0.05    0.26 
Q14   1   0.7736  0.9206 -0.0026  11.00000  0.05    0.25 
Q15   1   1.0084  0.1609  0.3779  11.00000  0.05    0.25 
Q16   1   0.8520  1.2592 -0.1117  11.00000  0.05    0.24 
Q17   1   0.7121 -0.3307  0.8754  11.00000  0.05    0.23 
Q18   1   0.5588  0.6230  0.5174  11.00000  0.05    0.23 
Q19   1   0.5614 -0.0511  0.8939  11.00000  0.05    0.23 
Q20   1   1.1122 -0.0929  0.2768  11.00000  0.05    0.23 
;
_shelx_res_checksum              69610
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.51580(14) 0.65815(12) 0.40051(13) 0.0276(3) Uani 1 1 d D U . . .
H1 H 0.512(7) 0.546(4) 0.464(6) 0.041 Uiso 0.5 1 d D U P . .
O2 O 0.81011(18) 0.56329(14) 0.28345(17) 0.0426(3) Uani 1 1 d . U . . .
C1 C 0.68145(19) 0.68289(15) 0.29706(16) 0.0216(3) Uani 1 1 d . U . . .
C2 C 0.71171(17) 0.87538(15) 0.18979(15) 0.0204(2) Uani 1 1 d . U . . .
C3 C 0.73738(17) 1.03452(15) 0.10549(15) 0.0199(2) Uani 1 1 d . U . . .
C4 C 0.76728(19) 1.22780(16) 0.00416(18) 0.0243(3) Uani 1 1 d . U . . .
H4A H 0.8984 1.2389 -0.0684 0.036 Uiso 1 1 calc R U . . .
H4B H 0.7604 1.3124 0.0916 0.036 Uiso 1 1 calc R U . . .
H4C H 0.6632 1.2627 -0.0791 0.036 Uiso 1 1 calc R U . . .
N1S N 1.1289(3) 0.1594(3) 0.3627(3) 0.0195(4) Uani 0.5 1 d . U P A -1
N2S N 0.9257(3) -0.0345(2) 0.5485(2) 0.0173(4) Uani 0.5 1 d . U P A -1
C1S C 1.2161(18) 0.3325(16) 0.2424(16) 0.0300(18) Uani 0.5 1 d . U P A -1
H1SA H 1.3588 0.3365 0.2553 0.045 Uiso 0.5 1 calc R U P A -1
H1SB H 1.1496 0.4432 0.2784 0.045 Uiso 0.5 1 calc R U P A -1
H1SC H 1.1978 0.3330 0.1133 0.045 Uiso 0.5 1 calc R U P A -1
C2S C 1.2181(4) -0.0157(3) 0.3877(3) 0.0217(4) Uani 0.5 1 d . U P A -1
H2S H 1.3466 -0.0449 0.3344 0.026 Uiso 0.5 1 calc R U P A -1
C3S C 1.0883(10) -0.1399(11) 0.5032(9) 0.0211(9) Uani 0.5 1 d . U P A -1
H3S H 1.1068 -0.2720 0.5438 0.025 Uiso 0.5 1 calc R U P A -1
C4S C 0.9512(10) 0.1420(11) 0.4615(9) 0.0202(9) Uani 0.5 1 d . U P A -1
H4S H 0.8576 0.2414 0.4680 0.024 Uiso 0.5 1 calc R U P A -1
C5S C 0.7396(4) -0.1050(3) 0.6649(3) 0.0221(4) Uani 0.5 1 d . U P A -1
H5SA H 0.6294 -0.0959 0.5859 0.027 Uiso 0.5 1 calc R U P A -1
H5SB H 0.7048 -0.0247 0.7564 0.027 Uiso 0.5 1 calc R U P A -1
C6S C 0.7619(16) -0.3064(15) 0.7649(16) 0.0254(14) Uani 0.5 1 d . U P A -1
H6SA H 0.7866 -0.3874 0.6746 0.038 Uiso 0.5 1 calc R U P A -1
H6SB H 0.6392 -0.3465 0.8459 0.038 Uiso 0.5 1 calc R U P A -1
H6SC H 0.8742 -0.3165 0.8395 0.038 Uiso 0.5 1 calc R U P A -1
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 0.0258(5) 0.0175(4) 0.0331(5) 0.0072(3) 0.0004(4) -0.0003(3)
O2 0.0469(7) 0.0173(5) 0.0510(7) 0.0072(4) 0.0192(5) 0.0105(4)
C1 0.0278(6) 0.0135(5) 0.0218(5) -0.0001(4) -0.0015(4) -0.0007(4)
C2 0.0226(5) 0.0149(5) 0.0218(5) -0.0005(4) -0.0012(4) 0.0000(4)
C3 0.0214(5) 0.0141(5) 0.0226(5) -0.0002(4) -0.0025(4) 0.0005(4)
C4 0.0268(6) 0.0138(5) 0.0292(6) 0.0033(4) -0.0037(4) -0.0018(4)
N1S 0.0248(9) 0.0117(7) 0.0204(8) -0.0002(6) -0.0017(7) 0.0015(6)
N2S 0.0227(9) 0.0106(7) 0.0176(7) -0.0016(6) -0.0019(6) 0.0024(6)
C1S 0.042(4) 0.014(2) 0.027(2) 0.0061(17) 0.003(2) -0.004(2)
C2S 0.0259(11) 0.0132(9) 0.0242(10) -0.0017(7) -0.0004(8) 0.0049(7)
C3S 0.027(2) 0.0142(13) 0.022(2) -0.0055(15) -0.0038(14) 0.0087(15)
C4S 0.029(2) 0.0121(12) 0.020(2) -0.0045(13) -0.0030(14) 0.0044(15)
C5S 0.0248(11) 0.0136(9) 0.0258(10) -0.0018(7) 0.0014(8) 0.0019(8)
C6S 0.027(2) 0.016(3) 0.030(2) 0.0044(16) -0.0065(17) -0.0038(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 109(3)
O2 C1 O1 126.13(11)
O2 C1 C2 119.76(11)
O1 C1 C2 114.11(10)
C3 C2 C1 178.48(12)
C2 C3 C4 179.58(14)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C4S N1S C2S 107.9(4)
C4S N1S C1S 127.0(6)
C2S N1S C1S 125.0(5)
C4S N2S C3S 109.7(3)
C4S N2S C5S 123.3(3)
C3S N2S C5S 126.9(3)
N1S C1S H1SA 109.5
N1S C1S H1SB 109.5
H1SA C1S H1SB 109.5
N1S C1S H1SC 109.5
H1SA C1S H1SC 109.5
H1SB C1S H1SC 109.5
C3S C2S N1S 107.5(3)
C3S C2S H2S 126.2
N1S C2S H2S 126.2
C2S C3S N2S 105.7(5)
C2S C3S H3S 127.1
N2S C3S H3S 127.1
N2S C4S N1S 109.1(5)
N2S C4S H4S 125.4
N1S C4S H4S 125.4
N2S C5S C6S 111.4(5)
N2S C5S H5SA 109.3
C6S C5S H5SA 109.3
N2S C5S H5SB 109.3
C6S C5S H5SB 109.3
H5SA C5S H5SB 108.0
C5S C6S H6SA 109.5
C5S C6S H6SB 109.5
H6SA C6S H6SB 109.5
C5S C6S H6SC 109.5
H6SA C6S H6SC 109.5
H6SB C6S H6SC 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2787(15)
O1 H1 0.846(18)
O2 C1 1.2209(16)
C1 C2 1.4604(15)
C2 C3 1.1976(15)
C3 C4 1.4512(16)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
N1S C4S 1.329(6)
N1S C2S 1.374(3)
N1S C1S 1.473(11)
N2S C4S 1.312(7)
N2S C3S 1.371(6)
N2S C5S 1.481(3)
C1S H1SA 0.9800
C1S H1SB 0.9800
C1S H1SC 0.9800
C2S C3S 1.366(7)
C2S H2S 0.9500
C3S H3S 0.9500
C4S H4S 0.9500
C5S C6S 1.503(11)
C5S H5SA 0.9900
C5S H5SB 0.9900
C6S H6SA 0.9800
C6S H6SB 0.9800
C6S H6SC 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.846(18) 1.609(18) 2.4519(18) 174(5) 2_666