# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_GL_SA\rietveld
_database_code_depnum_ccdc_archive 'CCDC 1062628'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            GL-SA
_chemical_formula_moiety         'C15 H21 N3 O3 S, C4 H6 O4'
_chemical_formula_sum            'C19 H27 N3 O7 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         441.50
_chemical_melting_point          135.17

_symmetry_space_group_name_H-M   P1
_symmetry_Int_Tables_number      1
_symmetry_cell_setting           triclinic
_space_group_name_Hall           P1
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
_cell_length_a                   13.6952
_cell_length_b                   11.1812
_cell_length_c                   10.7534
_cell_angle_alpha                82.3900
_cell_angle_beta                 92.5433
_cell_angle_gamma                90.1698
_cell_volume                     1630.537
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1056
_cell_measurement_theta_min      5.00
_cell_measurement_theta_max      45.00
_cell_measurement_temperature    298.15

_exptl_crystal_description       ?
_pd_char_colour                  white

_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             234

_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?


_diffrn_ambient_temperature      298.15

_diffrn_source                   'ceremic X-ray tube'
_diffrn_source_type              'long fine focus'

_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  none

_diffrn_measurement_device_type  "PANalytical X'Pert PRO"

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            3250
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         5.00
_diffrn_reflns_theta_max         45.00
_diffrn_reflns_theta_full        ?
_diffrn_measured_fraction_theta_max ?
_diffrn_measured_fraction_theta_full ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'polynomial order'

_pd_proc_ls_prof_R_factor        18.56
_pd_proc_ls_prof_wR_factor       14.71
_refine_ls_matrix_type           full
_refine_ls_goodness_of_fit_all   0.782

_refine_ls_number_reflns         425
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    ?

_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
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
C1 C 0.40909 0.73033 0.03050 0.00000 Uiso 1.00
C2 C 0.49005 0.65381 0.04260 0.00000 Uiso 1.00
C3 C 0.47948 0.52978 0.05250 0.00000 Uiso 1.00
C4 C 0.38652 0.47535 0.05183 0.00000 Uiso 1.00
C5 C 0.30530 0.55372 0.04295 0.00000 Uiso 1.00
C6 C 0.31678 0.67780 0.03159 0.00000 Uiso 1.00
C7 C 0.42186 0.86531 0.01503 0.00000 Uiso 1.00
S8 S 0.37246 0.31563 0.06254 0.00000 Uiso 1.00
N9 N 0.32345 0.29778 -0.07852 0.00000 Uiso 1.00
C10 C 0.38899 0.24302 -0.14083 0.00000 Uiso 1.00
N11 N 0.45403 0.31064 -0.21211 0.00000 Uiso 1.00
N12 N 0.46677 0.43577 -0.20847 0.00000 Uiso 1.00
C13 C 0.55626 0.48131 -0.26777 0.00000 Uiso 1.00
C14 C 0.54479 0.61953 -0.28362 0.00000 Uiso 1.00
C15 C 0.43260 0.63845 -0.29738 0.00000 Uiso 1.00
C16 C 0.39167 0.50910 -0.28485 0.00000 Uiso 1.00
C17 C 0.41395 0.72286 -0.42096 0.00000 Uiso 1.00
C18 C 0.50932 0.79556 -0.43143 0.00000 Uiso 1.00
C19 C 0.58709 0.69614 -0.39821 0.00000 Uiso 1.00
O20 O 0.29770 0.28234 0.14816 0.00000 Uiso 1.00
O21 O 0.46658 0.26217 0.08621 0.00000 Uiso 1.00
O22 O 0.38771 0.13455 -0.13724 0.00000 Uiso 1.00
H23 H 0.56361 0.69377 0.04179 0.00000 Uiso 1.00
H24 H 0.54618 0.47419 0.05938 0.00000 Uiso 1.00
H25 H 0.23035 0.51802 0.04336 0.00000 Uiso 1.00
H26 H 0.25180 0.73681 0.02234 0.00000 Uiso 1.00
H27 H 0.35135 0.91283 0.01016 0.00000 Uiso 1.00
H28 H 0.45856 0.89730 -0.07239 0.00000 Uiso 1.00
H29 H 0.46610 0.89464 0.09354 0.00000 Uiso 1.00
H30 H 0.27641 0.23140 -0.05616 0.00000 Uiso 1.00
H31 H 0.51417 0.26082 -0.21512 0.00000 Uiso 1.00
H32 H 0.62106 0.44847 -0.20931 0.00000 Uiso 1.00
H33 H 0.56226 0.44883 -0.35983 0.00000 Uiso 1.00
H34 H 0.57312 0.65387 -0.19763 0.00000 Uiso 1.00
H35 H 0.40811 0.68435 -0.21970 0.00000 Uiso 1.00
H36 H 0.38082 0.47814 -0.37791 0.00000 Uiso 1.00
H37 H 0.32083 0.50090 -0.24039 0.00000 Uiso 1.00
H38 H 0.40655 0.67054 -0.50090 0.00000 Uiso 1.00
H39 H 0.34733 0.77774 -0.42183 0.00000 Uiso 1.00
H40 H 0.51269 0.85816 -0.36010 0.00000 Uiso 1.00
H41 H 0.51746 0.84983 -0.52359 0.00000 Uiso 1.00
H42 H 0.66126 0.72943 -0.37945 0.00000 Uiso 1.00
H43 H 0.59075 0.64352 -0.47774 0.00000 Uiso 1.00
C44 C 0.16907 0.00258 0.13592 0.00000 Uiso 1.00
C45 C 0.19297 -0.00386 0.27848 0.00000 Uiso 1.00
C46 C 0.17493 -0.13065 0.35122 0.00000 Uiso 1.00
C47 C 0.23987 -0.22930 0.32846 0.00000 Uiso 1.00
O48 O 0.31681 -0.17944 0.26589 0.00000 Uiso 1.00
O49 O 0.23066 -0.33654 0.36050 0.00000 Uiso 1.00
O50 O 0.13854 -0.07638 0.07946 0.00000 Uiso 1.00
O51 O 0.18610 0.11684 0.07949 0.00000 Uiso 1.00
H52 H 0.14350 0.06006 0.31480 0.00000 Uiso 1.00
H53 H 0.26873 0.02675 0.29390 0.00000 Uiso 1.00
H54 H 0.09923 -0.15828 0.33175 0.00000 Uiso 1.00
H55 H 0.18176 -0.12382 0.45270 0.00000 Uiso 1.00
H56 H 0.21460 0.16582 0.13978 0.00000 Uiso 1.00
H57 H 0.35859 -0.24239 0.24446 0.00000 Uiso 1.00
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.393
C1 C6 1.392
C1 C7 1.507
C2 C3 1.384
C2 H23 1.101
C3 C4 1.410
C3 H24 1.101
C4 C5 1.410
C4 S8 1.785
C5 C6 1.386
C5 H25 1.100
C6 H26 1.102
C7 H27 1.099
C7 H28 1.103
C7 H29 1.102
S8 N9 1.667
S8 O20 1.423
S8 O21 1.421
N9 C10 1.340
N9 H30 0.994
C10 N11 1.362
C10 O22 1.208
N11 N12 1.415
N11 H31 1.000
N12 C13 1.466
N12 C16 1.469
C13 C14 1.540
C13 H32 1.100
C13 H33 1.105
C14 C15 1.550
C14 C19 1.539
C14 H34 1.102
C15 C16 1.541
C15 C17 1.537
C15 H35 1.101
C16 H36 1.105
C16 H37 1.099
C17 C18 1.537
C17 H38 1.103
C17 H39 1.100
C18 C19 1.538
C18 H40 1.104
C18 H41 1.101
C19 H42 1.100
C19 H43 1.103
C44 C45 1.546
C44 O50 1.200
C44 O51 1.364
C45 C46 1.550
C45 H52 1.106
C45 H53 1.104
C46 C47 1.471
C46 H54 1.100
C46 H55 1.104
C47 O48 1.354
C47 O49 1.211
O48 H57 0.966
O51 H56 0.971

#===END

####################################################################### 
# 
# 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_rietveld
_database_code_depnum_ccdc_archive 'CCDC 1062630'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            GL-MA
_chemical_formula_moiety         'C15 H21 N3 O3 S, C4 H6 O5'
_chemical_formula_sum            'C19 H27 N3 O8 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         457.50
_chemical_melting_point          157.26

_symmetry_space_group_name_H-M   P21/C
_symmetry_Int_Tables_number      14
_symmetry_cell_setting           monoclinic
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z+1/2
-x,-y,-z
x,-y+1/2,z+1/2
_cell_length_a                   10.8484
_cell_length_b                   14.3701
_cell_length_c                   13.0037
_cell_angle_alpha                90.0000
_cell_angle_beta                 125.8402
_cell_angle_gamma                90.0000
_cell_volume                     1643.340
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1614
_cell_measurement_theta_min      5.00
_cell_measurement_theta_max      45.00
_cell_measurement_temperature    298.15

_exptl_crystal_description       ?
_pd_char_colour                  white

_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968

_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?


_diffrn_ambient_temperature      298.15

_diffrn_source                   'ceremic X-ray tube'
_diffrn_source_type              'long fine focus'

_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  none

_diffrn_measurement_device_type  "PANalytical X'Pert PRO"

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            3250
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         5.00
_diffrn_reflns_theta_max         45.00
_diffrn_reflns_theta_full        ?
_diffrn_measured_fraction_theta_max ?
_diffrn_measured_fraction_theta_full ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'polynomial order'

_pd_proc_ls_prof_R_factor        4.75
_pd_proc_ls_prof_wR_factor       7.15
_refine_ls_matrix_type           full
_refine_ls_goodness_of_fit_all   0.894

_refine_ls_number_reflns         234
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    ?

_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
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
C1 C -0.17091 -0.49246 -0.08860 0.00000 Uiso 1.00
C2 C -0.13798 -0.39913 -0.05596 0.00000 Uiso 1.00
C3 C -0.16413 -0.35720 0.02560 0.00000 Uiso 1.00
C4 C -0.22867 -0.40621 0.07674 0.00000 Uiso 1.00
C5 C -0.25702 -0.50083 0.04477 0.00000 Uiso 1.00
C6 C -0.22934 -0.54243 -0.03515 0.00000 Uiso 1.00
C7 C -0.15576 -0.53819 -0.18422 0.00000 Uiso 1.00
S8 S -0.32845 -0.34906 0.12903 0.00000 Uiso 1.00
N9 N -0.40734 -0.26066 0.02752 0.00000 Uiso 1.00
C10 C -0.55188 -0.27387 -0.07177 0.00000 Uiso 1.00
N11 N -0.57988 -0.24817 -0.18334 0.00000 Uiso 1.00
N12 N -0.59522 -0.32064 -0.26253 0.00000 Uiso 1.00
C13 C -0.55637 -0.41336 -0.20847 0.00000 Uiso 1.00
C14 C -0.53568 -0.47091 -0.29505 0.00000 Uiso 1.00
C15 C -0.48831 -0.39860 -0.35342 0.00000 Uiso 1.00
C16 C -0.48654 -0.30728 -0.29118 0.00000 Uiso 1.00
C17 C -0.61490 -0.40416 -0.49608 0.00000 Uiso 1.00
C18 C -0.69192 -0.49792 -0.51834 0.00000 Uiso 1.00
C19 C -0.68856 -0.50995 -0.40190 0.00000 Uiso 1.00
O20 O -0.43852 -0.41216 0.11235 0.00000 Uiso 1.00
O21 O -0.22993 -0.30890 0.25004 0.00000 Uiso 1.00
O22 O -0.65230 -0.29799 -0.06307 0.00000 Uiso 1.00
H23 H -0.09488 -0.35776 -0.09946 0.00000 Uiso 1.00
H24 H -0.14468 -0.28264 0.04029 0.00000 Uiso 1.00
H25 H -0.31935 -0.54152 0.07113 0.00000 Uiso 1.00
H26 H -0.26803 -0.61402 -0.06694 0.00000 Uiso 1.00
H27 H -0.07107 -0.50374 -0.19149 0.00000 Uiso 1.00
H28 H -0.26572 -0.53663 -0.27698 0.00000 Uiso 1.00
H29 H -0.12470 -0.61186 -0.16333 0.00000 Uiso 1.00
H30 H -0.40804 -0.21385 0.08308 0.00000 Uiso 1.00
H31 H -0.49858 -0.20373 -0.16527 0.00000 Uiso 1.00
H32 H -0.64506 -0.43997 -0.20153 0.00000 Uiso 1.00
H33 H -0.45331 -0.41195 -0.11374 0.00000 Uiso 1.00
H34 H -0.45734 -0.52939 -0.24834 0.00000 Uiso 1.00
H35 H -0.37611 -0.41142 -0.33159 0.00000 Uiso 1.00
H36 H -0.37236 -0.29363 -0.20412 0.00000 Uiso 1.00
H37 H -0.52185 -0.24524 -0.35042 0.00000 Uiso 1.00
H38 H -0.57810 -0.39374 -0.55757 0.00000 Uiso 1.00
H39 H -0.69806 -0.34990 -0.51977 0.00000 Uiso 1.00
H40 H -0.62673 -0.55356 -0.52239 0.00000 Uiso 1.00
H41 H -0.80796 -0.49866 -0.60567 0.00000 Uiso 1.00
H42 H -0.78037 -0.46748 -0.41492 0.00000 Uiso 1.00
H43 H -0.69999 -0.58152 -0.38020 0.00000 Uiso 1.00
O44 O 0.05550 -0.15630 -0.10982 0.00000 Uiso 1.00
C45 C 0.06816 -0.18962 -0.00674 0.00000 Uiso 1.00
O46 O 0.13643 -0.25864 0.05138 0.00000 Uiso 1.00
C47 C -0.02126 -0.12841 0.02123 0.00000 Uiso 1.00
H48 H -0.13138 -0.16355 -0.02548 0.00000 Uiso 1.00
H49 H -0.04076 -0.06175 -0.02493 0.00000 Uiso 1.00
C50 C 0.06326 -0.11662 0.16395 0.00000 Uiso 1.00
O51 O 0.10127 -0.02226 0.19990 0.00000 Uiso 1.00
H52 H 0.16568 -0.16056 0.21641 0.00000 Uiso 1.00
C53 C -0.03118 -0.15012 0.21216 0.00000 Uiso 1.00
O54 O -0.16534 -0.16261 0.15316 0.00000 Uiso 1.00
O55 O 0.06571 -0.17153 0.33634 0.00000 Uiso 1.00
H56 H 0.16976 -0.15364 0.37206 0.00000 Uiso 1.00
H57 H 0.09865 -0.20192 -0.13488 0.00000 Uiso 1.00
H58 H 0.16717 -0.00427 0.17730 0.00000 Uiso 1.00
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.389
C1 C6 1.384
C1 C7 1.498
C2 C3 1.386
C2 H23 1.096
C3 C4 1.405
C3 H24 1.087
C4 C5 1.402
C4 S8 1.781
C5 C6 1.376
C5 H25 1.090
C6 H26 1.096
C7 H27 1.095
C7 H28 1.092
C7 H29 1.096
S8 N9 1.663
S8 O20 1.411
S8 O21 1.408
N9 C10 1.338
N9 H30 0.990
C10 N11 1.348
C10 O22 1.210
N11 N12 1.404
N11 H31 0.999
N12 C13 1.449
N12 C16 1.442
C13 C14 1.516
C13 H32 1.087
C13 H33 1.075
C14 C15 1.542
C14 C19 1.516
C14 H34 1.092
C15 C16 1.536
C15 C17 1.533
C15 H35 1.092
C16 H36 1.101
C16 H37 1.091
C17 C18 1.521
C17 H38 1.093
C17 H39 1.091
C18 C19 1.503
C18 H40 1.089
C18 H41 1.096
C19 H42 1.094
C19 H43 1.093
O44 C45 1.353
O44 H57 0.966
C45 O46 1.203
C45 C47 1.503
C47 H48 1.096
C47 H49 1.083
C47 C50 1.523
C50 O51 1.415
C50 H52 1.101
C50 C53 1.558
O51 H58 0.954
C53 O54 1.196
C53 O55 1.349
O55 H56 0.971

#===END
