# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4p03GPA
_database_code_depnum_ccdc_archive 'CCDC 1493074'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_4p03GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.343 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.8787(3)
_cell_length_b                   8.2985(4)
_cell_length_c                   13.070(2)
_cell_angle_alpha                81.714(8)
_cell_angle_beta                 87.395(8)
_cell_angle_gamma                82.183(4)
_cell_volume                     624.86(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    956
_cell_measurement_theta_min      2.4950
_cell_measurement_theta_max      26.8380

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         4030000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3135
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.339
_diffrn_measured_fraction_theta_full 0.343
_diffrn_reflns_Laue_measured_fraction_max 0.339
_diffrn_reflns_Laue_measured_fraction_full 0.343
_diffrn_reflns_point_group_measured_fraction_max 0.339
_diffrn_reflns_point_group_measured_fraction_full 0.343
_reflns_number_total             866
_reflns_number_gt                647
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.2059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         866
_refine_ls_number_parameters     191
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      0.981
_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
S1 S 0.23057(17) 0.99388(14) 0.3901(3) 0.0169(19) Uani 1 1 d . U . . .
O3 O 0.0442(5) 0.6767(4) 0.4137(7) 0.022(3) Uani 1 1 d . U . . .
N1 N 0.2583(5) 0.8413(4) 0.4828(8) 0.020(3) Uani 1 1 d . U . . .
H1 H 0.3424 0.8477 0.5339 0.025 Uiso 1 1 calc R U . . .
N3 N 0.3123(6) 0.6326(5) 0.6521(9) 0.018(3) Uani 1 1 d . U . . .
C4 C 0.4067(9) 0.9286(7) 0.2910(14) 0.020(3) Uani 1 1 d . U . . .
O2 O 0.0019(4) 1.0269(4) 0.3550(6) 0.022(3) Uani 1 1 d . U . . .
O1 O 0.3264(5) 1.1220(4) 0.4295(7) 0.020(4) Uani 1 1 d . U . . .
C8 C 0.1540(8) 0.7011(7) 0.4845(12) 0.015(3) Uani 1 1 d . U . . .
N2 N 0.1973(7) 0.5939(6) 0.5684(10) 0.022(3) Uani 1 1 d . U . . .
H2 H 0.1543 0.4982 0.5721 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6339(7) 0.8649(5) 0.3116(10) 0.018(3) Uani 1 1 d . U . . .
H3 H 0.6885 0.8512 0.3784 0.022 Uiso 1 1 calc R U . . .
C1 C 0.7021(9) 0.8386(7) 0.1292(14) 0.018(4) Uani 1 1 d . U . . .
C5 C 0.3291(9) 0.9466(7) 0.1906(14) 0.019(3) Uani 1 1 d . U . . .
H5 H 0.1781 0.9916 0.1768 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4703(7) 0.8997(5) 0.1129(11) 0.019(3) Uani 1 1 d . U . . .
H6 H 0.4125 0.9079 0.0470 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7761(9) 0.8225(7) 0.2298(14) 0.017(4) Uani 1 1 d . U . . .
H2A H 0.9286 0.7811 0.2429 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1585(7) 0.6246(6) 0.7457(11) 0.020(3) Uani 1 1 d . U . . .
H14A H 0.1660 0.5112 0.7778 0.024 Uiso 1 1 calc R U . . .
H14B H 0.0016 0.6616 0.7248 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8645(8) 0.7890(6) 0.0443(11) 0.023(4) Uani 1 1 d . U . . .
H7A H 0.9677 0.8696 0.0267 0.035 Uiso 1 1 calc R U . . .
H7B H 0.7791 0.7814 -0.0153 0.035 Uiso 1 1 calc R U . . .
H7C H 0.9509 0.6843 0.0672 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2192(7) 0.7277(6) 0.8244(11) 0.023(3) Uani 1 1 d . U . . .
H13A H 0.2643 0.8292 0.7879 0.028 Uiso 1 1 calc R U . . .
H13B H 0.0828 0.7560 0.8661 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4081(7) 0.6468(6) 0.8951(11) 0.028(4) Uani 1 1 d . U . . .
H12A H 0.3645 0.5450 0.9318 0.034 Uiso 1 1 calc R U . . .
H12B H 0.4276 0.7179 0.9459 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6348(7) 0.6102(6) 0.8375(11) 0.027(4) Uani 1 1 d . U . . .
H11A H 0.6703 0.7097 0.7947 0.032 Uiso 1 1 calc R U . . .
H11B H 0.7559 0.5759 0.8870 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6292(8) 0.4785(6) 0.7707(13) 0.022(4) Uani 1 1 d . U . . .
H10A H 0.5364 0.3988 0.8067 0.026 Uiso 1 1 calc R U . . .
H10B H 0.7843 0.4226 0.7648 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5388(8) 0.5288(6) 0.6619(12) 0.019(4) Uani 1 1 d . U . . .
H9A H 0.6509 0.5875 0.6207 0.023 Uiso 1 1 calc R U . . .
H9B H 0.5288 0.4297 0.6319 0.023 Uiso 1 1 calc R U . . .


_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
S1 O2 1.418(4) . ?
S1 O1 1.436(4) . ?
S1 N1 1.618(9) . ?
S1 C4 1.723(14) . ?
O3 C8 1.209(14) . ?
N1 C8 1.383(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.408(14) . ?
N3 C9 1.484(6) . ?
N3 C14 1.486(16) . ?
C4 C5 1.39(3) . ?
C4 C3 1.391(8) . ?
C8 N2 1.320(18) . ?
N2 H2 0.8600 . ?
C3 C2 1.383(17) . ?
C3 H3 0.9300 . ?
C1 C2 1.39(3) . ?
C1 C6 1.402(7) . ?
C1 C7 1.497(17) . ?
C5 C6 1.350(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.512(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.500(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.517(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.499(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.52(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 118.41(19) . . ?
O2 S1 N1 111.2(3) . . ?
O1 S1 N1 104.4(4) . . ?
O2 S1 C4 108.3(5) . . ?
O1 S1 C4 108.8(3) . . ?
N1 S1 C4 104.9(5) . . ?
C8 N1 S1 123.6(8) . . ?
C8 N1 H1 118.2 . . ?
S1 N1 H1 118.2 . . ?
N2 N3 C9 109.1(7) . . ?
N2 N3 C14 109.5(5) . . ?
C9 N3 C14 116.4(10) . . ?
C5 C4 C3 119.8(13) . . ?
C5 C4 S1 121.2(5) . . ?
C3 C4 S1 118.9(12) . . ?
O3 C8 N2 123.7(6) . . ?
O3 C8 N1 123.0(12) . . ?
N2 C8 N1 113.3(10) . . ?
C8 N2 N3 121.5(5) . . ?
C8 N2 H2 119.3 . . ?
N3 N2 H2 119.3 . . ?
C2 C3 C4 118.0(12) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C2 C1 C6 116.7(13) . . ?
C2 C1 C7 120.4(7) . . ?
C6 C1 C7 122.9(13) . . ?
C6 C5 C4 120.8(7) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 121.5(13) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C3 C2 C1 123.2(7) . . ?
C3 C2 H2A 118.4 . . ?
C1 C2 H2A 118.4 . . ?
N3 C14 C13 113.3(5) . . ?
N3 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 C14 114.8(5) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C13 C12 C11 112.5(11) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C10 C11 C12 112.0(5) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C10 C9 118.1(6) . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C9 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
N3 C9 C10 116.8(11) . . ?
N3 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
N3 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 40.0(7) . . . . ?
O1 S1 N1 C8 168.8(6) . . . . ?
C4 S1 N1 C8 -76.8(6) . . . . ?
O2 S1 C4 C5 13.1(8) . . . . ?
O1 S1 C4 C5 -116.9(7) . . . . ?
N1 S1 C4 C5 131.9(7) . . . . ?
O2 S1 C4 C3 -170.3(5) . . . . ?
O1 S1 C4 C3 59.7(7) . . . . ?
N1 S1 C4 C3 -51.5(5) . . . . ?
S1 N1 C8 O3 4.6(10) . . . . ?
S1 N1 C8 N2 -178.9(6) . . . . ?
O3 C8 N2 N3 -175.4(7) . . . . ?
N1 C8 N2 N3 8.1(10) . . . . ?
C9 N3 N2 C8 -113.8(8) . . . . ?
C14 N3 N2 C8 117.9(7) . . . . ?
C5 C4 C3 C2 0.5(9) . . . . ?
S1 C4 C3 C2 -176.2(4) . . . . ?
C3 C4 C5 C6 1.4(11) . . . . ?
S1 C4 C5 C6 178.0(4) . . . . ?
C4 C5 C6 C1 -3.1(10) . . . . ?
C2 C1 C6 C5 2.7(10) . . . . ?
C7 C1 C6 C5 -178.6(5) . . . . ?
C4 C3 C2 C1 -0.8(10) . . . . ?
C6 C1 C2 C3 -0.7(11) . . . . ?
C7 C1 C2 C3 -179.5(4) . . . . ?
N2 N3 C14 C13 -156.1(6) . . . . ?
C9 N3 C14 C13 79.7(6) . . . . ?
N3 C14 C13 C12 -82.9(10) . . . . ?
C14 C13 C12 C11 63.0(8) . . . . ?
C13 C12 C11 C10 -68.6(9) . . . . ?
C12 C11 C10 C9 86.2(11) . . . . ?
N2 N3 C9 C10 -147.2(7) . . . . ?
C14 N3 C9 C10 -22.7(7) . . . . ?
C11 C10 C9 N3 -51.2(9) . . . . ?

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
N1 H1 O1 0.86 2.08 2.815(7) 142.7 2_676
N2 H2 O3 0.86 1.97 2.792(5) 160.8 2_566

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_0p33GPA
_database_code_depnum_ccdc_archive 'CCDC 1493069'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_0p33GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.355 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        tolazamide
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.3489(4)
_cell_length_b                   8.8785(5)
_cell_length_c                   13.387(3)
_cell_angle_alpha                81.965(10)
_cell_angle_beta                 85.674(10)
_cell_angle_gamma                84.251(5)
_cell_volume                     742.01(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    762
_cell_measurement_theta_min      2.3220
_cell_measurement_theta_max      26.5790

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         330000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3722
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.337
_diffrn_measured_fraction_theta_full 0.355
_diffrn_reflns_Laue_measured_fraction_max 0.337
_diffrn_reflns_Laue_measured_fraction_full 0.355
_diffrn_reflns_point_group_measured_fraction_max 0.337
_diffrn_reflns_point_group_measured_fraction_full 0.355
_reflns_number_total             1016
_reflns_number_gt                652
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1016
_refine_ls_number_parameters     210
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.862
_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
S1 S 0.2490(2) 0.97659(16) 0.3921(3) 0.037(2) Uani 1 1 d . U . . .
O3 O 0.0609(6) 0.6741(4) 0.4147(9) 0.044(5) Uani 1 1 d . U . . .
N1 N 0.2547(6) 0.8330(4) 0.4823(9) 0.033(4) Uani 1 1 d . U . . .
H1 H 0.3265 0.8408 0.5330 0.040 Uiso 1 1 calc R U . . .
N3 N 0.2937(8) 0.6395(6) 0.6495(11) 0.039(4) Uani 1 1 d . U . . .
C4 C 0.4198(10) 0.9154(8) 0.2958(16) 0.038(4) Uani 1 1 d . U . . .
O2 O 0.0411(5) 1.0081(4) 0.3577(7) 0.040(5) Uani 1 1 d . U . . .
O1 O 0.3424(5) 1.0947(4) 0.4310(7) 0.041(5) Uani 1 1 d . U . . .
C8 C 0.1566(9) 0.6999(8) 0.4861(15) 0.034(4) Uani 1 1 d . U . . .
N2 N 0.1848(9) 0.6025(7) 0.5660(13) 0.045(4) Uani 1 1 d . U . . .
H2 H 0.1382 0.5141 0.5697 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6308(8) 0.8660(6) 0.3126(12) 0.038(6) Uani 1 1 d . U . . .
H3 H 0.6801 0.8604 0.3768 0.045 Uiso 1 1 calc R U . . .
C1 C 0.7000(12) 0.8333(10) 0.1373(18) 0.043(6) Uani 1 1 d . U . . .
C5 C 0.3506(12) 0.9231(9) 0.1990(18) 0.042(4) Uani 1 1 d . U . . .
H5 H 0.2097 0.9553 0.1871 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4883(9) 0.8837(7) 0.1203(14) 0.049(5) Uani 1 1 d . U . . .
H6 H 0.4404 0.8906 0.0557 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7650(12) 0.8258(10) 0.2340(18) 0.041(6) Uani 1 1 d . U . . .
H2A H 0.9054 0.7922 0.2462 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1527(9) 0.6390(8) 0.7399(14) 0.045(5) Uani 1 1 d . U . . .
H14A H 0.1493 0.5351 0.7735 0.053 Uiso 1 1 calc R U . . .
H14B H 0.0103 0.6756 0.7209 0.053 Uiso 1 1 calc R U . . .
C7 C 0.8456(11) 0.7881(9) 0.0534(16) 0.062(7) Uani 1 1 d . U . . .
H7A H 0.8667 0.8760 0.0044 0.093 Uiso 1 1 calc R U . . .
H7B H 0.7855 0.7127 0.0221 0.093 Uiso 1 1 calc R U . . .
H7C H 0.9793 0.7461 0.0790 0.093 Uiso 1 1 calc R U . . .
C13 C 0.2186(11) 0.7346(9) 0.8101(15) 0.056(6) Uani 1 1 d . U . . .
H13A H 0.0945 0.7645 0.8522 0.068 Uiso 1 1 calc R U . . .
H13B H 0.2646 0.8271 0.7708 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3942(12) 0.6676(11) 0.8800(18) 0.075(6) Uani 1 1 d D U . . .
H12A H 0.4732 0.7508 0.8920 0.090 Uiso 0.40(2) 1 calc R U P A 1
H12B H 0.3272 0.6278 0.9445 0.090 Uiso 0.40(2) 1 calc R U P A 1
H12C H 0.4130 0.7382 0.9271 0.090 Uiso 0.60(2) 1 calc R U P A 2
H12D H 0.3554 0.5725 0.9186 0.090 Uiso 0.60(2) 1 calc R U P A 2
C11A C 0.552(4) 0.542(3) 0.846(3) 0.070(8) Uani 0.40(2) 1 d D U P A 1
H11A H 0.6740 0.5297 0.8867 0.084 Uiso 0.40(2) 1 calc R U P A 1
H11B H 0.4870 0.4468 0.8553 0.084 Uiso 0.40(2) 1 calc R U P A 1
C10A C 0.625(4) 0.580(3) 0.736(2) 0.056(8) Uani 0.40(2) 1 d D U P A 1
H10A H 0.6341 0.6892 0.7227 0.068 Uiso 0.40(2) 1 calc R U P A 1
H10B H 0.7670 0.5310 0.7269 0.068 Uiso 0.40(2) 1 calc R U P A 1
C11B C 0.5987(18) 0.639(2) 0.817(2) 0.062(8) Uani 0.60(2) 1 d D U P A 2
H11C H 0.6235 0.7306 0.7707 0.075 Uiso 0.60(2) 1 calc R U P A 2
H11D H 0.7154 0.6183 0.8614 0.075 Uiso 0.60(2) 1 calc R U P A 2
C10B C 0.595(3) 0.5076(16) 0.7579(15) 0.053(7) Uani 0.60(2) 1 d D U P A 2
H10C H 0.7409 0.4664 0.7457 0.063 Uiso 0.60(2) 1 calc R U P A 2
H10D H 0.5232 0.4285 0.8006 0.063 Uiso 0.60(2) 1 calc R U P A 2
C9 C 0.4937(10) 0.5362(8) 0.6578(14) 0.049(6) Uani 1 1 d D U . . .
H9A H 0.4600 0.4313 0.6762 0.059 Uiso 0.40(2) 1 calc R U P A 1
H9B H 0.5740 0.5435 0.5930 0.059 Uiso 0.40(2) 1 calc R U P A 1
H9C H 0.5972 0.5778 0.6071 0.059 Uiso 0.60(2) 1 calc R U P A 2
H9D H 0.4652 0.4381 0.6403 0.059 Uiso 0.60(2) 1 calc R U P A 2


_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
S1 O2 1.419(5) . ?
S1 O1 1.431(5) . ?
S1 N1 1.628(10) . ?
S1 C4 1.732(16) . ?
O3 C8 1.230(18) . ?
N1 C8 1.384(7) . ?
N1 H1 0.8600 . ?
N3 N2 1.450(17) . ?
N3 C14 1.449(19) . ?
N3 C9 1.492(8) . ?
C4 C5 1.39(3) . ?
C4 C3 1.392(10) . ?
C8 N2 1.29(2) . ?
N2 H2 0.8600 . ?
C3 C2 1.37(2) . ?
C3 H3 0.9300 . ?
C1 C6 1.398(11) . ?
C1 C2 1.38(3) . ?
C1 C7 1.47(2) . ?
C5 C6 1.38(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.461(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.53(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11B 1.512(14) . ?
C12 C11A 1.517(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C11A C10A 1.503(18) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C10A C9 1.502(16) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11B C10B 1.503(16) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C10B C9 1.510(16) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 H9D 0.9700 . ?

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 S1 O1 118.5(2) . . ?
O2 S1 N1 109.8(3) . . ?
O1 S1 N1 105.4(5) . . ?
O2 S1 C4 109.3(6) . . ?
O1 S1 C4 107.9(3) . . ?
N1 S1 C4 105.0(6) . . ?
C8 N1 S1 127.0(10) . . ?
C8 N1 H1 116.5 . . ?
S1 N1 H1 116.5 . . ?
N2 N3 C14 110.8(7) . . ?
N2 N3 C9 107.6(8) . . ?
C14 N3 C9 116.5(12) . . ?
C5 C4 C3 119.0(15) . . ?
C5 C4 S1 120.2(7) . . ?
C3 C4 S1 120.7(14) . . ?
O3 C8 N2 123.1(7) . . ?
O3 C8 N1 121.3(15) . . ?
N2 C8 N1 115.5(13) . . ?
C8 N2 N3 121.1(7) . . ?
C8 N2 H2 119.4 . . ?
N3 N2 H2 119.4 . . ?
C2 C3 C4 119.6(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C1 C2 118.1(17) . . ?
C6 C1 C7 120.0(18) . . ?
C2 C1 C7 122.0(10) . . ?
C6 C5 C4 120.8(9) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.2(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C2 C1 122.4(9) . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 H2A 118.8 . . ?
N3 C14 C13 112.3(7) . . ?
N3 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 118.1(7) . . ?
C14 C13 H13A 107.8 . . ?
C12 C13 H13A 107.8 . . ?
C14 C13 H13B 107.8 . . ?
C12 C13 H13B 107.8 . . ?
H13A C13 H13B 107.1 . . ?
C11B C12 C13 109.2(15) . . ?
C11A C12 C13 118.0(17) . . ?
C11A C12 H12A 107.8 . . ?
C13 C12 H12A 107.8 . . ?
C11A C12 H12B 107.8 . . ?
C13 C12 H12B 107.8 . . ?
H12A C12 H12B 107.1 . . ?
C11B C12 H12C 109.8 . . ?
C13 C12 H12C 109.8 . . ?
C11B C12 H12D 109.8 . . ?
C13 C12 H12D 109.8 . . ?
H12C C12 H12D 108.3 . . ?
C10A C11A C12 111(2) . . ?
C10A C11A H11A 109.4 . . ?
C12 C11A H11A 109.4 . . ?
C10A C11A H11B 109.4 . . ?
C12 C11A H11B 109.4 . . ?
H11A C11A H11B 108.0 . . ?
C9 C10A C11A 118(2) . . ?
C9 C10A H10A 107.7 . . ?
C11A C10A H10A 107.7 . . ?
C9 C10A H10B 107.7 . . ?
C11A C10A H10B 107.7 . . ?
H10A C10A H10B 107.1 . . ?
C10B C11B C12 112.6(13) . . ?
C10B C11B H11C 109.1 . . ?
C12 C11B H11C 109.1 . . ?
C10B C11B H11D 109.1 . . ?
C12 C11B H11D 109.1 . . ?
H11C C11B H11D 107.8 . . ?
C9 C10B C11B 118.6(15) . . ?
C9 C10B H10C 107.7 . . ?
C11B C10B H10C 107.7 . . ?
C9 C10B H10D 107.7 . . ?
C11B C10B H10D 107.7 . . ?
H10C C10B H10D 107.1 . . ?
C10A C9 N3 110.1(12) . . ?
N3 C9 C10B 118.3(13) . . ?
C10A C9 H9A 109.6 . . ?
N3 C9 H9A 109.6 . . ?
C10A C9 H9B 109.6 . . ?
N3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N3 C9 H9C 107.7 . . ?
C10B C9 H9C 107.7 . . ?
N3 C9 H9D 107.7 . . ?
C10B C9 H9D 107.7 . . ?
H9C C9 H9D 107.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 41.7(8) . . . . ?
O1 S1 N1 C8 170.4(7) . . . . ?
C4 S1 N1 C8 -75.8(8) . . . . ?
O2 S1 C4 C5 8.5(10) . . . . ?
O1 S1 C4 C5 -121.7(9) . . . . ?
N1 S1 C4 C5 126.3(9) . . . . ?
O2 S1 C4 C3 -175.1(6) . . . . ?
O1 S1 C4 C3 54.7(8) . . . . ?
N1 S1 C4 C3 -57.4(7) . . . . ?
S1 N1 C8 O3 4.3(12) . . . . ?
S1 N1 C8 N2 180.0(8) . . . . ?
O3 C8 N2 N3 -178.3(8) . . . . ?
N1 C8 N2 N3 6.2(14) . . . . ?
C14 N3 N2 C8 116.5(10) . . . . ?
C9 N3 N2 C8 -115.1(11) . . . . ?
C5 C4 C3 C2 -0.2(13) . . . . ?
S1 C4 C3 C2 -176.6(6) . . . . ?
C3 C4 C5 C6 -0.4(15) . . . . ?
S1 C4 C5 C6 176.0(5) . . . . ?
C4 C5 C6 C1 0.8(13) . . . . ?
C2 C1 C6 C5 -0.4(15) . . . . ?
C7 C1 C6 C5 178.7(7) . . . . ?
C4 C3 C2 C1 0.5(15) . . . . ?
C6 C1 C2 C3 -0.2(17) . . . . ?
C7 C1 C2 C3 -179.3(6) . . . . ?
N2 N3 C14 C13 -155.6(8) . . . . ?
C9 N3 C14 C13 81.0(8) . . . . ?
N3 C14 C13 C12 -81.5(15) . . . . ?
C14 C13 C12 C11B 65.1(13) . . . . ?
C14 C13 C12 C11A 26(2) . . . . ?
C13 C12 C11A C10A 44(3) . . . . ?
C12 C11A C10A C9 -86(3) . . . . ?
C13 C12 C11B C10B -71.2(19) . . . . ?
C12 C11B C10B C9 83(2) . . . . ?
C11A C10A C9 N3 73(2) . . . . ?
N2 N3 C9 C10A 174.2(15) . . . . ?
C14 N3 C9 C10A -60.7(15) . . . . ?
N2 N3 C9 C10B -157.5(12) . . . . ?
C14 N3 C9 C10B -32.5(12) . . . . ?
C11B C10B C9 N3 -40(2) . . . . ?

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
N1 H1 O1 0.86 2.33 3.047(8) 140.5 2_676
N2 H2 O3 0.86 2.17 3.010(6) 164.6 2_566

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_046GPa
_database_code_depnum_ccdc_archive 'CCDC 1495203'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2278(5)
_cell_length_b                   9.026(2)
_cell_length_c                   13.3215(14)
_cell_angle_alpha                79.608(13)
_cell_angle_beta                 86.913(8)
_cell_angle_gamma                85.990(13)
_cell_volume                     734.09(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    711
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       460000
_cell_measurement_theta_min      3.0030
_cell_measurement_theta_max      26.0120
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1316
_diffrn_reflns_av_unetI/netI     0.1314
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.333
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3799
_diffrn_reflns_point_group_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         460000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.347
_diffrn_measured_fraction_theta_max 0.333
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                521
_reflns_number_total             1000
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1000
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1630
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+1.9148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.2054
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0231(4) 0.2634(8) 0.2224(2) 0.059(2) Uani 1 1 d . U . . .
O3 O -0.0677(9) 0.4589(17) 0.3824(5) 0.062(5) Uani 1 1 d . U . . .
O2 O -0.2072(8) 0.2648(17) 0.2315(5) 0.062(8) Uani 1 1 d . U . . .
C8 C 0.0657(15) 0.350(3) 0.4036(8) 0.060(2) Uani 1 1 d . U . . .
N2 N 0.1633(10) 0.318(2) 0.4924(6) 0.060(2) Uani 1 1 d . U . . .
H2 H 0.1333 0.3718 0.5388 0.072 Uiso 1 1 calc R . . . .
C4 C 0.0937(12) 0.445(3) 0.1597(8) 0.056(3) Uani 1 1 d . U . . .
N1 N 0.1171(11) 0.241(2) 0.3360(6) 0.059(2) Uani 1 1 d . U . . .
H1 H 0.2001 0.1628 0.3568 0.071 Uiso 1 1 calc R . . . .
O1 O 0.1457(12) 0.148(2) 0.1781(6) 0.069(4) Uani 1 1 d . U . . .
N3 N 0.3199(11) 0.191(2) 0.5094(6) 0.061(2) Uani 1 1 d . U . . .
C3 C 0.3089(12) 0.472(2) 0.1307(7) 0.057(3) Uani 1 1 d . U . . .
H3 H 0.4169 0.3974 0.1493 0.068 Uiso 1 1 calc R . . . .
C6 C -0.0095(13) 0.695(2) 0.0790(7) 0.057(3) Uani 1 1 d . U . . .
H6 H -0.1178 0.7706 0.0616 0.068 Uiso 1 1 calc R . . . .
C5 C -0.0620(13) 0.554(3) 0.1336(8) 0.057(3) Uani 1 1 d . U . . .
H5 H -0.2052 0.5352 0.1519 0.068 Uiso 1 1 calc R . . . .
C14 C 0.2499(14) 0.090(3) 0.6023(7) 0.061(2) Uani 1 1 d . U . . .
H14A H 0.3469 0.0002 0.6090 0.073 Uiso 1 1 calc R . . . .
H14B H 0.1088 0.0590 0.5904 0.073 Uiso 1 1 calc R . . . .
C1 C 0.2045(13) 0.724(3) 0.0507(8) 0.057(3) Uani 1 1 d . U . . .
C2 C 0.3579(13) 0.603(3) 0.0772(8) 0.057(3) Uani 1 1 d . U . . .
H2A H 0.5009 0.6167 0.0558 0.068 Uiso 1 1 calc R . . . .
C9 C 0.5357(13) 0.249(2) 0.5129(7) 0.061(2) Uani 1 1 d D U . . .
H9A H 0.6406 0.1671 0.5036 0.074 Uiso 1 1 calc R . . . .
H9B H 0.5526 0.3277 0.4538 0.074 Uiso 1 1 calc R . . . .
C7 C 0.2684(16) 0.870(3) -0.0052(9) 0.073(8) Uani 1 1 d . U . . .
H7A H 0.1793 0.9013 -0.0628 0.110 Uiso 1 1 calc GR . . . .
H7B H 0.4164 0.8607 -0.0286 0.110 Uiso 1 1 calc GR . . . .
H7C H 0.2514 0.9431 0.0391 0.110 Uiso 1 1 calc GR . . . .
C13 C 0.2346(13) 0.139(3) 0.7019(7) 0.061(2) Uani 1 1 d . U . . .
H13A H 0.1389 0.0741 0.7469 0.073 Uiso 1 1 calc R . . . .
H13B H 0.1674 0.2404 0.6927 0.073 Uiso 1 1 calc R . . . .
C12 C 0.4442(12) 0.139(2) 0.7557(8) 0.061(2) Uani 1 1 d D U . . .
H12A H 0.4124 0.1881 0.8142 0.074 Uiso 1 1 calc R . . . .
H12B H 0.4892 0.0346 0.7819 0.074 Uiso 1 1 calc R . . . .
C11 C 0.6294(13) 0.210(2) 0.6982(8) 0.062(2) Uani 1 1 d D U . . .
H11A H 0.6932 0.2687 0.7416 0.074 Uiso 1 1 calc R . . . .
H11B H 0.7354 0.1297 0.6872 0.074 Uiso 1 1 calc R . . . .
C10 C 0.5964(14) 0.307(2) 0.5998(6) 0.062(2) Uani 1 1 d D U . . .
H10A H 0.4870 0.3849 0.6112 0.074 Uiso 1 1 calc R . . . .
H10B H 0.7290 0.3571 0.5801 0.074 Uiso 1 1 calc R . . . .


_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
S1 O2 1.433(6) . ?
S1 C4 1.78(2) . ?
S1 N1 1.625(9) . ?
S1 O1 1.444(18) . ?
O3 C8 1.24(2) . ?
C8 N2 1.335(12) . ?
C8 N1 1.45(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.44(2) . ?
C4 C3 1.400(11) . ?
C4 C5 1.34(2) . ?
N1 H1 0.8600 . ?
N3 C14 1.465(13) . ?
N3 C9 1.480(15) . ?
C3 H3 0.9300 . ?
C3 C2 1.31(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.40(2) . ?
C6 C1 1.394(12) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.47(2) . ?
C1 C2 1.41(2) . ?
C1 C7 1.46(3) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.434(17) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.522(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.469(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.456(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 107.7(7) . . ?
O2 S1 N1 108.9(4) . . ?
O2 S1 O1 120.4(10) . . ?
N1 S1 C4 105.8(9) . . ?
O1 S1 C4 110.5(7) . . ?
O1 S1 N1 102.6(7) . . ?
O3 C8 N2 123(2) . . ?
O3 C8 N1 122.4(10) . . ?
N2 C8 N1 114.5(17) . . ?
C8 N2 H2 120.4 . . ?
C8 N2 N3 119.2(16) . . ?
N3 N2 H2 120.4 . . ?
C3 C4 S1 120.2(13) . . ?
C5 C4 S1 119.6(9) . . ?
C5 C4 C3 120.1(15) . . ?
S1 N1 H1 118.9 . . ?
C8 N1 S1 122.3(11) . . ?
C8 N1 H1 118.9 . . ?
N2 N3 C14 107.6(9) . . ?
N2 N3 C9 108.8(15) . . ?
C14 N3 C9 114.7(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(14) . . ?
C2 C3 H3 120.0 . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C1 C6 C5 120.2(13) . . ?
C4 C5 C6 120.2(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N3 C14 H14A 107.0 . . ?
N3 C14 H14B 107.0 . . ?
N3 C14 C13 121.2(19) . . ?
H14A C14 H14B 106.8 . . ?
C13 C14 H14A 107.0 . . ?
C13 C14 H14B 107.0 . . ?
C6 C1 C2 116.5(15) . . ?
C6 C1 C7 122.4(14) . . ?
C2 C1 C7 121.1(9) . . ?
C3 C2 C1 123.1(9) . . ?
C3 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
N3 C9 H9A 107.1 . . ?
N3 C9 H9B 107.1 . . ?
H9A C9 H9B 106.8 . . ?
C10 C9 N3 121.1(9) . . ?
C10 C9 H9A 107.1 . . ?
C10 C9 H9B 107.1 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C14 C13 C12 116.9(10) . . ?
H13A C13 H13B 107.3 . . ?
C12 C13 H13A 108.1 . . ?
C12 C13 H13B 108.1 . . ?
C13 C12 H12A 107.5 . . ?
C13 C12 H12B 107.5 . . ?
H12A C12 H12B 107.0 . . ?
C11 C12 C13 119.1(7) . . ?
C11 C12 H12A 107.5 . . ?
C11 C12 H12B 107.5 . . ?
C12 C11 H11A 107.5 . . ?
C12 C11 H11B 107.5 . . ?
H11A C11 H11B 107.0 . . ?
C10 C11 C12 119.2(7) . . ?
C10 C11 H11A 107.5 . . ?
C10 C11 H11B 107.5 . . ?
C9 C10 C11 121.7(16) . . ?
C9 C10 H10A 106.9 . . ?
C9 C10 H10B 106.9 . . ?
C11 C10 H10A 106.9 . . ?
C11 C10 H10B 106.9 . . ?
H10A C10 H10B 106.7 . . ?

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
N2 H2 O3 0.86 2.01 2.85(2) 165.6 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 174.5(15) . . . . ?
S1 C4 C5 C6 -176.4(14) . . . . ?
O3 C8 N2 N3 -178.5(12) . . . . ?
O3 C8 N1 S1 6(2) . . . . ?
O2 S1 C4 C3 -173.1(13) . . . . ?
O2 S1 C4 C5 2.0(17) . . . . ?
O2 S1 N1 C8 -61.6(15) . . . . ?
C8 N2 N3 C14 -123.5(14) . . . . ?
C8 N2 N3 C9 111.6(13) . . . . ?
N2 C8 N1 S1 -177.3(7) . . . . ?
N2 N3 C14 C13 -63.3(13) . . . . ?
N2 N3 C9 C10 74.0(13) . . . . ?
C4 S1 N1 C8 53.9(12) . . . . ?
C4 C3 C2 C1 3(3) . . . . ?
N1 S1 C4 C3 70.6(16) . . . . ?
N1 S1 C4 C5 -114.3(14) . . . . ?
N1 C8 N2 N3 5.3(17) . . . . ?
O1 S1 C4 C3 -39.8(15) . . . . ?
O1 S1 C4 C5 135.3(14) . . . . ?
O1 S1 N1 C8 169.7(12) . . . . ?
N3 C14 C13 C12 -78.5(18) . . . . ?
N3 C9 C10 C11 68.9(17) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C6 C1 C2 C3 -4(3) . . . . ?
C5 C4 C3 C2 -1(3) . . . . ?
C5 C6 C1 C2 2(2) . . . . ?
C5 C6 C1 C7 -179.3(18) . . . . ?
C14 N3 C9 C10 -47(2) . . . . ?
C14 C13 C12 C11 49(3) . . . . ?
C1 C6 C5 C4 1(3) . . . . ?
C9 N3 C14 C13 58.0(18) . . . . ?
C7 C1 C2 C3 177.3(18) . . . . ?
C13 C12 C11 C10 14(3) . . . . ?
C12 C11 C10 C9 -67(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6p83GPA
_database_code_depnum_ccdc_archive 'CCDC 1493078'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_6p83GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.345 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.7365(3)
_cell_length_b                   8.0902(4)
_cell_length_c                   12.894(2)
_cell_angle_alpha                82.422(8)
_cell_angle_beta                 88.028(8)
_cell_angle_gamma                82.178(4)
_cell_volume                     587.59(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    885
_cell_measurement_theta_min      2.5570
_cell_measurement_theta_max      26.6400

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         6830000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2957
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.337
_diffrn_measured_fraction_theta_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.337
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_point_group_measured_fraction_max 0.337
_diffrn_reflns_point_group_measured_fraction_full 0.345
_reflns_number_total             809
_reflns_number_gt                599
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.3141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         809
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
S1 S 0.22261(18) 1.00095(15) 0.3890(3) 0.0112(4) Uiso 1 1 d . . . . .
O3 O 0.0374(5) 0.6790(4) 0.4111(7) 0.0145(9) Uiso 1 1 d . . . . .
N1 N 0.2581(6) 0.8465(5) 0.4809(9) 0.0143(10) Uiso 1 1 d . . . . .
H1 H 0.3488 0.8535 0.5314 0.017 Uiso 1 1 calc R U . . .
N3 N 0.3168(6) 0.6330(5) 0.6520(9) 0.0127(10) Uiso 1 1 d . . . . .
C4 C 0.4000(8) 0.9354(6) 0.2856(13) 0.0121(12) Uiso 1 1 d . . . . .
O2 O -0.0118(5) 1.0326(4) 0.3528(7) 0.0143(9) Uiso 1 1 d . . . . .
O1 O 0.3178(5) 1.1341(4) 0.4293(7) 0.0156(9) Uiso 1 1 d . . . . .
C8 C 0.1524(8) 0.7032(6) 0.4837(11) 0.0093(11) Uiso 1 1 d . . . . .
N2 N 0.1988(6) 0.5925(6) 0.5688(10) 0.0187(11) Uiso 1 1 d . . . . .
H2 H 0.1549 0.4944 0.5722 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6321(7) 0.8657(6) 0.3090(11) 0.0145(12) Uiso 1 1 d . . . . .
H3 H 0.6867 0.8492 0.3771 0.017 Uiso 1 1 calc R U . . .
C1 C 0.6980(9) 0.8410(7) 0.1283(13) 0.0141(13) Uiso 1 1 d . . . . .
C5 C 0.3152(9) 0.9523(6) 0.1872(13) 0.0133(12) Uiso 1 1 d . . . . .
H5 H 0.1595 0.9967 0.1733 0.016 Uiso 1 1 calc R U . . .
C6 C 0.4630(7) 0.9030(6) 0.1103(12) 0.0155(12) Uiso 1 1 d . . . . .
H6 H 0.4059 0.9108 0.0429 0.019 Uiso 1 1 calc R U . . .
C2 C 0.7765(9) 0.8226(6) 0.2259(12) 0.0095(12) Uiso 1 1 d . . . . .
H2A H 0.9331 0.7794 0.2385 0.011 Uiso 1 1 calc R U . . .
C14 C 0.1603(8) 0.6236(6) 0.7447(12) 0.0140(12) Uiso 1 1 d . . . . .
H14A H 0.1681 0.5071 0.7757 0.017 Uiso 1 1 calc R U . . .
H14B H -0.0003 0.6617 0.7228 0.017 Uiso 1 1 calc R U . . .
C7 C 0.8647(8) 0.7876(7) 0.0410(12) 0.0218(13) Uiso 1 1 d . . . . .
H7A H 0.9940 0.8524 0.0352 0.033 Uiso 1 1 calc R U . . .
H7B H 0.7821 0.8063 -0.0239 0.033 Uiso 1 1 calc R U . . .
H7C H 0.9234 0.6703 0.0565 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2199(8) 0.7262(6) 0.8257(11) 0.0163(12) Uiso 1 1 d . . . . .
H13A H 0.0787 0.7569 0.8661 0.020 Uiso 1 1 calc R U . . .
H13B H 0.2704 0.8293 0.7907 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4100(8) 0.6390(7) 0.8998(12) 0.0194(13) Uiso 1 1 d . . . . .
H12A H 0.3640 0.5338 0.9338 0.023 Uiso 1 1 calc R U . . .
H12B H 0.4290 0.7093 0.9535 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6446(8) 0.6041(6) 0.8403(11) 0.0173(12) Uiso 1 1 d . . . . .
H11A H 0.6793 0.7073 0.7990 0.021 Uiso 1 1 calc R U . . .
H11B H 0.7698 0.5675 0.8901 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6379(8) 0.4721(6) 0.7695(13) 0.0141(12) Uiso 1 1 d . . . . .
H10A H 0.7971 0.4155 0.7631 0.017 Uiso 1 1 calc R U . . .
H10B H 0.5444 0.3894 0.8045 0.017 Uiso 1 1 calc R U . . .
C9 C 0.5457(8) 0.5226(6) 0.6618(12) 0.0129(12) Uiso 1 1 d . . . . .
H9A H 0.6621 0.5798 0.6202 0.016 Uiso 1 1 calc R U . . .
H9B H 0.5306 0.4212 0.6314 0.016 Uiso 1 1 calc R U . . .

_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
S1 O2 1.418(4) . ?
S1 O1 1.434(5) . ?
S1 N1 1.601(9) . ?
S1 C4 1.744(13) . ?
O3 C8 1.215(13) . ?
N1 C8 1.375(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.385(14) . ?
N3 C14 1.470(16) . ?
N3 C9 1.483(6) . ?
C4 C5 1.36(2) . ?
C4 C3 1.400(8) . ?
C8 N2 1.332(16) . ?
N2 H2 0.8600 . ?
C3 C2 1.383(16) . ?
C3 H3 0.9300 . ?
C1 C2 1.33(2) . ?
C1 C6 1.389(8) . ?
C1 C7 1.520(17) . ?
C5 C6 1.348(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.492(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.512(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.537(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.499(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.49(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 118.2(2) . . ?
O2 S1 N1 112.1(3) . . ?
O1 S1 N1 104.5(5) . . ?
O2 S1 C4 106.8(5) . . ?
O1 S1 C4 109.4(3) . . ?
N1 S1 C4 105.1(4) . . ?
C8 N1 S1 123.9(8) . . ?
C8 N1 H1 118.0 . . ?
S1 N1 H1 118.0 . . ?
N2 N3 C14 108.2(5) . . ?
N2 N3 C9 108.1(7) . . ?
C14 N3 C9 116.0(10) . . ?
C5 C4 C3 122.1(12) . . ?
C5 C4 S1 121.0(5) . . ?
C3 C4 S1 116.9(11) . . ?
O3 C8 N2 124.0(5) . . ?
O3 C8 N1 121.5(11) . . ?
N2 C8 N1 114.3(9) . . ?
C8 N2 N3 120.9(5) . . ?
C8 N2 H2 119.5 . . ?
N3 N2 H2 119.5 . . ?
C2 C3 C4 116.9(12) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C2 C1 C6 118.7(13) . . ?
C2 C1 C7 119.3(6) . . ?
C6 C1 C7 121.9(13) . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 122.1(13) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C1 C2 C3 122.0(6) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
N3 C14 C13 113.5(5) . . ?
N3 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 114.5(5) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C12 C11 110.4(10) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C10 C11 C12 111.9(5) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C9 C10 C11 119.2(6) . . ?
C9 C10 H10A 107.5 . . ?
C11 C10 H10A 107.5 . . ?
C9 C10 H10B 107.5 . . ?
C11 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
N3 C9 C10 116.7(11) . . ?
N3 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
N3 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 38.0(7) . . . . ?
O1 S1 N1 C8 167.1(6) . . . . ?
C4 S1 N1 C8 -77.7(6) . . . . ?
O2 S1 C4 C5 12.3(6) . . . . ?
O1 S1 C4 C5 -116.7(6) . . . . ?
N1 S1 C4 C5 131.6(6) . . . . ?
O2 S1 C4 C3 -167.9(4) . . . . ?
O1 S1 C4 C3 63.0(6) . . . . ?
N1 S1 C4 C3 -48.7(5) . . . . ?
S1 N1 C8 O3 5.9(10) . . . . ?
S1 N1 C8 N2 -177.8(5) . . . . ?
O3 C8 N2 N3 -175.4(7) . . . . ?
N1 C8 N2 N3 8.5(9) . . . . ?
C14 N3 N2 C8 118.3(7) . . . . ?
C9 N3 N2 C8 -115.3(8) . . . . ?
C5 C4 C3 C2 3.3(8) . . . . ?
S1 C4 C3 C2 -176.4(4) . . . . ?
C3 C4 C5 C6 -1.4(9) . . . . ?
S1 C4 C5 C6 178.4(4) . . . . ?
C4 C5 C6 C1 -1.9(8) . . . . ?
C2 C1 C6 C5 3.1(9) . . . . ?
C7 C1 C6 C5 -179.3(5) . . . . ?
C6 C1 C2 C3 -1.0(9) . . . . ?
C7 C1 C2 C3 -178.7(4) . . . . ?
C4 C3 C2 C1 -2.1(7) . . . . ?
N2 N3 C14 C13 -157.0(6) . . . . ?
C9 N3 C14 C13 81.4(7) . . . . ?
N3 C14 C13 C12 -84.4(10) . . . . ?
C14 C13 C12 C11 64.1(8) . . . . ?
C13 C12 C11 C10 -69.3(9) . . . . ?
C12 C11 C10 C9 86.2(11) . . . . ?
N2 N3 C9 C10 -146.8(6) . . . . ?
C14 N3 C9 C10 -25.0(6) . . . . ?
C11 C10 C9 N3 -48.9(8) . . . . ?

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
N1 H1 O1 0.86 2.01 2.762(8) 144.9 2_676
N2 H2 O3 0.86 1.89 2.714(5) 161.0 2_566

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_300GPa
_database_code_depnum_ccdc_archive 'CCDC 1495207'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8913(3)
_cell_length_b                   8.5944(15)
_cell_length_c                   12.8846(15)
_cell_angle_alpha                80.681(12)
_cell_angle_beta                 85.494(7)
_cell_angle_gamma                85.723(9)
_cell_volume                     640.51(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    758
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       3000000
_cell_measurement_theta_min      1.6180
_cell_measurement_theta_max      25.6430
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3249
_diffrn_reflns_point_group_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.330
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         1.605
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         3000000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.337
_diffrn_measured_fraction_theta_max 0.330
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                550
_reflns_number_total             868
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         868
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0211(3) 0.2521(6) 0.2183(2) 0.032(2) Uani 1 1 d . U . . .
O3 O -0.0683(7) 0.4522(14) 0.3796(5) 0.038(4) Uani 1 1 d . U . . .
O2 O -0.2224(7) 0.2520(13) 0.2325(4) 0.026(7) Uani 1 1 d . U . . .
C8 C 0.0650(12) 0.335(2) 0.4022(8) 0.032(2) Uani 1 1 d . U . . .
N2 N 0.1567(8) 0.3096(16) 0.4983(6) 0.033(2) Uani 1 1 d . U . . .
H2 H 0.1160 0.3667 0.5463 0.039 Uiso 1 1 calc R . . . .
C4 C 0.0898(11) 0.443(2) 0.1576(7) 0.027(3) Uani 1 1 d . U . . .
N1 N 0.1278(9) 0.2341(19) 0.3343(6) 0.033(2) Uani 1 1 d . U . . .
H1 H 0.2268 0.1576 0.3520 0.039 Uiso 1 1 calc R . . . .
O1 O 0.1507(9) 0.1361(16) 0.1675(5) 0.034(3) Uani 1 1 d . U . . .
N3 N 0.3262(9) 0.1797(17) 0.5131(5) 0.033(2) Uani 1 1 d . U . . .
C3 C 0.3181(11) 0.467(2) 0.1270(7) 0.028(3) Uani 1 1 d . U . . .
H3 H 0.4322 0.3881 0.1435 0.033 Uiso 1 1 calc R . . . .
C6 C -0.0241(10) 0.7026(19) 0.0749(7) 0.027(3) Uani 1 1 d . U . . .
H6 H -0.1393 0.7794 0.0554 0.033 Uiso 1 1 calc R . . . .
C5 C -0.0806(11) 0.560(2) 0.1334(7) 0.027(3) Uani 1 1 d . U . . .
H5 H -0.2316 0.5422 0.1563 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2617(12) 0.070(2) 0.6101(7) 0.033(2) Uani 1 1 d . U . . .
H14A H 0.3750 -0.0183 0.6181 0.040 Uiso 1 1 calc R . . . .
H14B H 0.1169 0.0282 0.6016 0.040 Uiso 1 1 calc R . . . .
C1 C 0.2007(10) 0.734(2) 0.0447(7) 0.027(3) Uani 1 1 d . U . . .
C2 C 0.3673(11) 0.612(2) 0.0714(7) 0.028(3) Uani 1 1 d . U . . .
H2A H 0.5189 0.6303 0.0505 0.033 Uiso 1 1 calc R . . . .
C9 C 0.5542(11) 0.2427(18) 0.5107(7) 0.033(2) Uani 1 1 d D U . . .
H9A H 0.5782 0.3135 0.4446 0.040 Uiso 1 1 calc R . . . .
H9B H 0.6679 0.1551 0.5104 0.040 Uiso 1 1 calc R . . . .
C7 C 0.2646(11) 0.891(2) -0.0114(7) 0.034(7) Uani 1 1 d . U . . .
H7A H 0.1489 0.9346 -0.0581 0.051 Uiso 1 1 calc GR . . . .
H7B H 0.4077 0.8792 -0.0514 0.051 Uiso 1 1 calc GR . . . .
H7C H 0.2786 0.9598 0.0390 0.051 Uiso 1 1 calc GR . . . .
C13 C 0.2401(11) 0.146(2) 0.7132(7) 0.033(2) Uani 1 1 d . U . . .
H13A H 0.1833 0.2553 0.6968 0.040 Uiso 1 1 calc R . . . .
H13B H 0.1300 0.0910 0.7633 0.040 Uiso 1 1 calc R . . . .
C12 C 0.4652(10) 0.1386(19) 0.7629(7) 0.033(2) Uani 1 1 d D U . . .
H12A H 0.4389 0.1838 0.8274 0.040 Uiso 1 1 calc R . . . .
H12B H 0.5147 0.0283 0.7826 0.040 Uiso 1 1 calc R . . . .
C11 C 0.6579(10) 0.2203(19) 0.6976(7) 0.034(2) Uani 1 1 d D U . . .
H11A H 0.7708 0.1399 0.6785 0.040 Uiso 1 1 calc R . . . .
H11B H 0.7295 0.2815 0.7415 0.040 Uiso 1 1 calc R . . . .
C10 C 0.5973(12) 0.3287(18) 0.5979(6) 0.034(2) Uani 1 1 d D U . . .
H10A H 0.4621 0.3948 0.6133 0.040 Uiso 1 1 calc R . . . .
H10B H 0.7210 0.3974 0.5748 0.040 Uiso 1 1 calc R . . . .


_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
S1 O2 1.432(5) . ?
S1 C4 1.765(14) . ?
S1 N1 1.646(8) . ?
S1 O1 1.423(14) . ?
O3 C8 1.238(16) . ?
C8 N2 1.368(10) . ?
C8 N1 1.35(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.441(15) . ?
C4 C3 1.392(9) . ?
C4 C5 1.379(16) . ?
N1 H1 0.8600 . ?
N3 C14 1.481(9) . ?
N3 C9 1.482(11) . ?
C3 H3 0.9300 . ?
C3 C2 1.371(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(16) . ?
C6 C1 1.384(8) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.57(2) . ?
C1 C2 1.399(17) . ?
C1 C7 1.484(18) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.489(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.511(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.506(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.510(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 107.4(5) . . ?
O2 S1 N1 109.2(4) . . ?
N1 S1 C4 103.3(7) . . ?
O1 S1 O2 121.1(7) . . ?
O1 S1 C4 110.3(6) . . ?
O1 S1 N1 104.0(6) . . ?
O3 C8 N2 119.4(16) . . ?
O3 C8 N1 122.2(8) . . ?
N1 C8 N2 118.4(13) . . ?
C8 N2 H2 122.4 . . ?
C8 N2 N3 115.1(13) . . ?
N3 N2 H2 122.4 . . ?
C3 C4 S1 117.4(10) . . ?
C5 C4 S1 120.4(6) . . ?
C5 C4 C3 121.9(11) . . ?
S1 N1 H1 119.0 . . ?
C8 N1 S1 122.0(9) . . ?
C8 N1 H1 119.0 . . ?
N2 N3 C14 109.5(7) . . ?
N2 N3 C9 109.1(11) . . ?
C14 N3 C9 114.9(5) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 C4 117.0(11) . . ?
C2 C3 H3 121.5 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C1 121.2(10) . . ?
C1 C6 H6 119.4 . . ?
C4 C5 C6 119.2(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N3 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
N3 C14 C13 114.5(14) . . ?
H14A C14 H14B 107.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C6 C1 C2 117.4(11) . . ?
C6 C1 C7 121.6(10) . . ?
C2 C1 C7 121.0(6) . . ?
C3 C2 C1 123.3(7) . . ?
C3 C2 H2A 118.4 . . ?
C1 C2 H2A 118.4 . . ?
N3 C9 H9A 108.0 . . ?
N3 C9 H9B 108.0 . . ?
N3 C9 C10 117.1(8) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C12 C13 C14 112.2(10) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 C13 117.1(5) . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C12 C11 C10 116.8(5) . . ?
H11A C11 H11B 107.3 . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C9 C10 C11 113.3(12) . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?

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
N2 H2 O3 0.86 1.95 2.77(2) 161.3 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 174.3(11) . . . . ?
S1 C4 C5 C6 -172.4(11) . . . . ?
O3 C8 N2 N3 -174.3(8) . . . . ?
O3 C8 N1 S1 -3.5(17) . . . . ?
O2 S1 C4 C3 -174.1(10) . . . . ?
O2 S1 C4 C5 0.3(13) . . . . ?
O2 S1 N1 C8 -56.3(13) . . . . ?
C8 N2 N3 C14 -125.9(10) . . . . ?
C8 N2 N3 C9 107.5(10) . . . . ?
N2 C8 N1 S1 178.1(6) . . . . ?
N2 N3 C14 C13 -59.9(10) . . . . ?
N2 N3 C9 C10 66.1(9) . . . . ?
C4 S1 N1 C8 57.8(10) . . . . ?
C4 C3 C2 C1 0(2) . . . . ?
N1 S1 C4 C3 70.5(12) . . . . ?
N1 S1 C4 C5 -115.2(11) . . . . ?
N1 C8 N2 N3 4.2(13) . . . . ?
O1 S1 C4 C3 -40.2(12) . . . . ?
O1 S1 C4 C5 134.2(11) . . . . ?
O1 S1 N1 C8 173.1(10) . . . . ?
N3 C14 C13 C12 -87.4(10) . . . . ?
N3 C9 C10 C11 80.7(10) . . . . ?
C3 C4 C5 C6 2(2) . . . . ?
C6 C1 C2 C3 -1(2) . . . . ?
C5 C4 C3 C2 0(2) . . . . ?
C5 C6 C1 C2 3(2) . . . . ?
C5 C6 C1 C7 -175.5(13) . . . . ?
C14 N3 C9 C10 -57.3(16) . . . . ?
C14 C13 C12 C11 59.9(18) . . . . ?
C1 C6 C5 C4 -3(2) . . . . ?
C9 N3 C14 C13 63.3(13) . . . . ?
C7 C1 C2 C3 177.2(13) . . . . ?
C13 C12 C11 C10 12(2) . . . . ?
C12 C11 C10 C9 -75.9(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_610GPa
_database_code_depnum_ccdc_archive 'CCDC 1495210'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7168(4)
_cell_length_b                   8.3457(14)
_cell_length_c                   12.6434(10)
_cell_angle_alpha                81.4960(10)
_cell_angle_beta                 84.436(7)
_cell_angle_gamma                85.470(11)
_cell_volume                     592.50(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    828
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       6100000
_cell_measurement_theta_min      1.6470
_cell_measurement_theta_max      26.3750
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.333
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2997
_diffrn_reflns_point_group_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.635
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         6100000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.344
_diffrn_measured_fraction_theta_max 0.333
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                558
_reflns_number_total             804
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         804
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.3191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0189(3) 0.2480(6) 0.21659(16) 0.0269(18) Uani 1 1 d . U . . .
O3 O -0.0667(6) 0.4513(13) 0.3771(4) 0.033(4) Uani 1 1 d . U . . .
O2 O -0.2315(6) 0.2439(12) 0.2343(4) 0.021(6) Uani 1 1 d . U . . .
C8 C 0.0680(10) 0.331(2) 0.4017(6) 0.0275(19) Uani 1 1 d . U . . .
N2 N 0.1551(7) 0.3034(15) 0.4988(4) 0.0276(19) Uani 1 1 d . U . . .
H2 H 0.1087 0.3619 0.5483 0.033 Uiso 1 1 calc R . . . .
C4 C 0.0885(9) 0.4391(19) 0.1563(6) 0.030(3) Uani 1 1 d . U . . .
N1 N 0.1336(8) 0.2270(16) 0.3320(5) 0.0274(18) Uani 1 1 d . U . . .
H1 H 0.2369 0.1486 0.3477 0.033 Uiso 1 1 calc R . . . .
O1 O 0.1510(7) 0.1309(14) 0.1607(4) 0.032(3) Uani 1 1 d . U . . .
N3 N 0.3296(8) 0.1710(15) 0.5142(4) 0.0277(19) Uani 1 1 d . U . . .
C3 C 0.3231(10) 0.4688(19) 0.1260(5) 0.030(3) Uani 1 1 d . U . . .
H3 H 0.4428 0.3908 0.1452 0.036 Uiso 1 1 calc R . . . .
C6 C -0.0334(9) 0.7029(18) 0.0717(5) 0.030(3) Uani 1 1 d . U . . .
H6 H -0.1540 0.7795 0.0517 0.036 Uiso 1 1 calc R . . . .
C5 C -0.0868(10) 0.5583(19) 0.1317(5) 0.030(3) Uani 1 1 d . U . . .
H5 H -0.2425 0.5402 0.1561 0.036 Uiso 1 1 calc R . . . .
C14 C 0.2625(10) 0.0657(19) 0.6151(5) 0.0276(19) Uani 1 1 d . U . . .
H14A H 0.3786 -0.0255 0.6239 0.033 Uiso 1 1 calc R . . . .
H14B H 0.1126 0.0225 0.6088 0.033 Uiso 1 1 calc R . . . .
C1 C 0.1985(9) 0.7364(19) 0.0402(5) 0.030(3) Uani 1 1 d . U . . .
C2 C 0.3734(10) 0.612(2) 0.0686(5) 0.030(3) Uani 1 1 d . U . . .
H2A H 0.5301 0.6305 0.0464 0.036 Uiso 1 1 calc R . . . .
C9 C 0.5589(10) 0.2415(17) 0.5095(5) 0.0282(19) Uani 1 1 d D U . . .
H9A H 0.5818 0.3108 0.4411 0.034 Uiso 1 1 calc R . . . .
H9B H 0.6805 0.1535 0.5099 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2723(10) 0.8903(19) -0.0190(6) 0.037(6) Uani 1 1 d . U . . .
H7A H 0.1657 0.9290 -0.0728 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.4285 0.8747 -0.0529 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.2713 0.9686 0.0296 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.2412(9) 0.1489(19) 0.7167(5) 0.0277(19) Uani 1 1 d . U . . .
H13A H 0.1866 0.2618 0.6988 0.033 Uiso 1 1 calc R . . . .
H13B H 0.1260 0.0968 0.7693 0.033 Uiso 1 1 calc R . . . .
C12 C 0.4746(9) 0.1395(18) 0.7641(5) 0.0281(19) Uani 1 1 d D U . . .
H12A H 0.5302 0.0261 0.7779 0.034 Uiso 1 1 calc R . . . .
H12B H 0.4489 0.1796 0.8327 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6680(9) 0.2321(17) 0.6967(5) 0.0286(19) Uani 1 1 d D U . . .
H11A H 0.7322 0.3002 0.7412 0.034 Uiso 1 1 calc R . . . .
H11B H 0.7934 0.1543 0.6765 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5970(10) 0.3379(17) 0.5959(5) 0.0286(19) Uani 1 1 d D U . . .
H10A H 0.4530 0.4021 0.6129 0.034 Uiso 1 1 calc R . . . .
H10B H 0.7188 0.4121 0.5699 0.034 Uiso 1 1 calc R . . . .


_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
S1 O2 1.430(4) . ?
S1 C4 1.722(13) . ?
S1 N1 1.638(6) . ?
S1 O1 1.417(12) . ?
O3 C8 1.239(14) . ?
C8 N2 1.351(8) . ?
C8 N1 1.33(2) . ?
N2 H2 0.8600 . ?
N2 N3 1.433(13) . ?
C4 C3 1.390(8) . ?
C4 C5 1.379(15) . ?
N1 H1 0.8600 . ?
N3 C14 1.475(8) . ?
N3 C9 1.471(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.340(16) . ?
C6 H6 0.9300 . ?
C6 C5 1.366(16) . ?
C6 C1 1.384(7) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.538(18) . ?
C1 C2 1.415(15) . ?
C1 C7 1.459(16) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.491(15) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.506(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.518(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.509(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 109.1(5) . . ?
O2 S1 N1 109.7(3) . . ?
N1 S1 C4 104.0(6) . . ?
O1 S1 O2 119.9(6) . . ?
O1 S1 C4 109.0(5) . . ?
O1 S1 N1 103.9(5) . . ?
O3 C8 N2 120.6(14) . . ?
O3 C8 N1 120.6(7) . . ?
N1 C8 N2 118.7(11) . . ?
C8 N2 H2 122.0 . . ?
C8 N2 N3 115.9(11) . . ?
N3 N2 H2 122.0 . . ?
C3 C4 S1 119.1(9) . . ?
C5 C4 S1 120.6(5) . . ?
C5 C4 C3 120.2(10) . . ?
S1 N1 H1 119.8 . . ?
C8 N1 S1 120.4(7) . . ?
C8 N1 H1 119.8 . . ?
N2 N3 C14 108.9(6) . . ?
N2 N3 C9 107.2(9) . . ?
C9 N3 C14 115.2(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.6(9) . . ?
C2 C3 H3 120.7 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C1 120.7(9) . . ?
C1 C6 H6 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.7 . . ?
N3 C14 H14A 108.5 . . ?
N3 C14 H14B 108.5 . . ?
N3 C14 C13 115.1(12) . . ?
H14A C14 H14B 107.5 . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C6 C1 C2 117.0(10) . . ?
C6 C1 C7 124.4(9) . . ?
C2 C1 C7 118.6(6) . . ?
C3 C2 C1 122.8(6) . . ?
C3 C2 H2A 118.6 . . ?
C1 C2 H2A 118.6 . . ?
N3 C9 H9A 107.9 . . ?
N3 C9 H9B 107.9 . . ?
N3 C9 C10 117.5(7) . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 C14 111.0(9) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C13 C12 C11 116.2(5) . . ?
H12A C12 H12B 107.4 . . ?
C11 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C10 C11 C12 116.2(4) . . ?
C10 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C9 C10 C11 112.5(11) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?

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
N2 H2 O3 0.86 1.93 2.746(18) 159.2 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 172.7(10) . . . . ?
S1 C4 C5 C6 -171.5(10) . . . . ?
O3 C8 N2 N3 -173.1(7) . . . . ?
O3 C8 N1 S1 -5.6(12) . . . . ?
O2 S1 C4 C3 -176.4(9) . . . . ?
O2 S1 C4 C5 -0.8(12) . . . . ?
O2 S1 N1 C8 -57.6(11) . . . . ?
C8 N2 N3 C14 -129.5(9) . . . . ?
C8 N2 N3 C9 105.3(9) . . . . ?
N2 C8 N1 S1 175.8(5) . . . . ?
N2 N3 C14 C13 -60.0(8) . . . . ?
N2 N3 C9 C10 65.5(8) . . . . ?
C4 S1 N1 C8 58.9(8) . . . . ?
C4 C3 C2 C1 2.0(19) . . . . ?
N1 S1 C4 C3 66.5(11) . . . . ?
N1 S1 C4 C5 -117.8(9) . . . . ?
N1 C8 N2 N3 5.4(12) . . . . ?
O1 S1 C4 C3 -43.8(10) . . . . ?
O1 S1 C4 C5 131.8(10) . . . . ?
O1 S1 N1 C8 173.0(8) . . . . ?
N3 C14 C13 C12 -88.3(10) . . . . ?
N3 C9 C10 C11 82.1(9) . . . . ?
C3 C4 C5 C6 4.1(19) . . . . ?
C6 C1 C2 C3 -2.0(18) . . . . ?
C5 C4 C3 C2 -3.0(19) . . . . ?
C5 C6 C1 C2 3.0(18) . . . . ?
C5 C6 C1 C7 -176.7(12) . . . . ?
C14 N3 C9 C10 -55.9(15) . . . . ?
C14 C13 C12 C11 65.8(16) . . . . ?
C1 C6 C5 C4 -4.1(19) . . . . ?
C9 N3 C14 C13 60.4(12) . . . . ?
C7 C1 C2 C3 177.7(12) . . . . ?
C13 C12 C11 C10 6.5(18) . . . . ?
C12 C11 C10 C9 -73.9(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5p45GPA
_database_code_depnum_ccdc_archive 'CCDC 1493076'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_5p45GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.344 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.7996(3)
_cell_length_b                   8.1816(4)
_cell_length_c                   12.978(3)
_cell_angle_alpha                82.064(9)
_cell_angle_beta                 87.702(9)
_cell_angle_gamma                82.134(4)
_cell_volume                     604.02(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    936
_cell_measurement_theta_min      2.5300
_cell_measurement_theta_max      27.1430

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         5450000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3047
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.340
_diffrn_measured_fraction_theta_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.340
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.340
_diffrn_reflns_point_group_measured_fraction_full 0.344
_reflns_number_total             841
_reflns_number_gt                629
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         841
_refine_ls_number_parameters     191
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      0.928
_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
S1 S 0.22628(17) 0.99762(14) 0.3897(3) 0.0175(18) Uani 1 1 d . U . . .
O3 O 0.0407(5) 0.6778(4) 0.4120(7) 0.017(3) Uani 1 1 d . U . . .
N1 N 0.2584(5) 0.8443(4) 0.4811(8) 0.020(2) Uani 1 1 d . U . . .
H1 H 0.3476 0.8512 0.5313 0.024 Uiso 1 1 calc R U . . .
N3 N 0.3153(6) 0.6330(5) 0.6517(9) 0.014(3) Uani 1 1 d . U . . .
C4 C 0.4039(8) 0.9325(7) 0.2866(13) 0.019(2) Uani 1 1 d . U . . .
O2 O -0.0067(4) 1.0306(3) 0.3545(6) 0.020(3) Uani 1 1 d . U . . .
O1 O 0.3213(4) 1.1287(4) 0.4297(7) 0.019(4) Uani 1 1 d . U . . .
C8 C 0.1532(8) 0.7013(6) 0.4855(12) 0.012(3) Uani 1 1 d . U . . .
N2 N 0.1977(7) 0.5937(6) 0.5681(10) 0.018(3) Uani 1 1 d . U . . .
H2 H 0.1542 0.4967 0.5715 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6319(7) 0.8649(5) 0.3121(11) 0.020(3) Uani 1 1 d . U . . .
H3 H 0.6842 0.8486 0.3800 0.024 Uiso 1 1 calc R U . . .
C1 C 0.7004(9) 0.8396(7) 0.1303(14) 0.020(4) Uani 1 1 d . U . . .
C5 C 0.3215(9) 0.9488(7) 0.1909(14) 0.020(3) Uani 1 1 d . U . . .
H5 H 0.1670 0.9922 0.1780 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4666(7) 0.9012(5) 0.1118(11) 0.021(3) Uani 1 1 d . U . . .
H6 H 0.4094 0.9097 0.0451 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7773(9) 0.8231(7) 0.2273(14) 0.020(4) Uani 1 1 d . U . . .
H2A H 0.9329 0.7824 0.2395 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1599(7) 0.6226(6) 0.7464(11) 0.015(3) Uani 1 1 d . U . . .
H14A H 0.0001 0.6585 0.7257 0.018 Uiso 1 1 calc R U . . .
H14B H 0.1706 0.5075 0.7783 0.018 Uiso 1 1 calc R U . . .
C7 C 0.8657(7) 0.7885(6) 0.0433(11) 0.025(4) Uani 1 1 d . U . . .
H7A H 0.9848 0.8603 0.0330 0.038 Uiso 1 1 calc R U . . .
H7B H 0.7810 0.7974 -0.0197 0.038 Uiso 1 1 calc R U . . .
H7C H 0.9360 0.6755 0.0616 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2201(7) 0.7266(6) 0.8248(10) 0.019(3) Uani 1 1 d . U . . .
H13A H 0.0808 0.7580 0.8652 0.022 Uiso 1 1 calc R U . . .
H13B H 0.2694 0.8280 0.7882 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4092(7) 0.6430(6) 0.8988(11) 0.021(3) Uani 1 1 d . U . . .
H12A H 0.3642 0.5397 0.9347 0.025 Uiso 1 1 calc R U . . .
H12B H 0.4287 0.7148 0.9504 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6395(7) 0.6066(6) 0.8391(11) 0.020(4) Uani 1 1 d . U . . .
H11A H 0.6743 0.7083 0.7972 0.025 Uiso 1 1 calc R U . . .
H11B H 0.7635 0.5708 0.8885 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6337(8) 0.4749(6) 0.7698(12) 0.015(4) Uani 1 1 d . U . . .
H10A H 0.7910 0.4183 0.7640 0.018 Uiso 1 1 calc R U . . .
H10B H 0.5398 0.3938 0.8050 0.018 Uiso 1 1 calc R U . . .
C9 C 0.5443(8) 0.5256(6) 0.6621(12) 0.016(4) Uani 1 1 d . U . . .
H9A H 0.6590 0.5839 0.6212 0.019 Uiso 1 1 calc R U . . .
H9B H 0.5327 0.4254 0.6316 0.019 Uiso 1 1 calc R U . . .


_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
S1 O2 1.422(4) . ?
S1 O1 1.436(4) . ?
S1 N1 1.599(9) . ?
S1 C4 1.753(13) . ?
O3 C8 1.228(14) . ?
N1 C8 1.385(5) . ?
N1 H1 0.8600 . ?
N3 N2 1.401(14) . ?
N3 C9 1.489(6) . ?
N3 C14 1.494(15) . ?
C4 C5 1.33(2) . ?
C4 C3 1.396(8) . ?
C8 N2 1.300(17) . ?
N2 H2 0.8600 . ?
C3 C2 1.410(18) . ?
C3 H3 0.9300 . ?
C1 C2 1.34(3) . ?
C1 C6 1.399(8) . ?
C1 C7 1.517(17) . ?
C5 C6 1.365(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.493(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.513(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.531(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.500(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.49(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 117.95(18) . . ?
O2 S1 N1 111.6(3) . . ?
O1 S1 N1 104.6(4) . . ?
O2 S1 C4 107.5(5) . . ?
O1 S1 C4 109.3(3) . . ?
N1 S1 C4 105.2(4) . . ?
C8 N1 S1 124.8(8) . . ?
C8 N1 H1 117.6 . . ?
S1 N1 H1 117.6 . . ?
N2 N3 C9 109.1(7) . . ?
N2 N3 C14 109.0(5) . . ?
C9 N3 C14 115.4(10) . . ?
C5 C4 C3 123.5(12) . . ?
C5 C4 S1 120.8(5) . . ?
C3 C4 S1 115.7(11) . . ?
O3 C8 N2 124.4(5) . . ?
O3 C8 N1 120.5(11) . . ?
N2 C8 N1 114.9(9) . . ?
C8 N2 N3 121.2(5) . . ?
C8 N2 H2 119.4 . . ?
N3 N2 H2 119.4 . . ?
C4 C3 C2 115.1(12) . . ?
C4 C3 H3 122.4 . . ?
C2 C3 H3 122.4 . . ?
C2 C1 C6 118.8(14) . . ?
C2 C1 C7 119.7(7) . . ?
C6 C1 C7 121.5(13) . . ?
C4 C5 C6 119.2(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.6(13) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C1 C2 C3 122.6(7) . . ?
C1 C2 H2A 118.7 . . ?
C3 C2 H2A 118.7 . . ?
C13 C14 N3 112.9(5) . . ?
C13 C14 H14A 109.0 . . ?
N3 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
N3 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 114.8(4) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C13 C12 C11 110.4(10) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C10 C11 C12 112.6(4) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C9 C10 C11 118.8(6) . . ?
C9 C10 H10A 107.6 . . ?
C11 C10 H10A 107.6 . . ?
C9 C10 H10B 107.6 . . ?
C11 C10 H10B 107.6 . . ?
H10A C10 H10B 107.1 . . ?
N3 C9 C10 116.8(11) . . ?
N3 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
N3 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 38.6(7) . . . . ?
O1 S1 N1 C8 167.2(6) . . . . ?
C4 S1 N1 C8 -77.7(6) . . . . ?
O2 S1 C4 C5 11.7(7) . . . . ?
O1 S1 C4 C5 -117.4(7) . . . . ?
N1 S1 C4 C5 130.8(7) . . . . ?
O2 S1 C4 C3 -168.5(4) . . . . ?
O1 S1 C4 C3 62.4(6) . . . . ?
N1 S1 C4 C3 -49.4(5) . . . . ?
S1 N1 C8 O3 6.4(10) . . . . ?
S1 N1 C8 N2 -178.2(6) . . . . ?
O3 C8 N2 N3 -176.1(7) . . . . ?
N1 C8 N2 N3 8.7(10) . . . . ?
C9 N3 N2 C8 -114.7(8) . . . . ?
C14 N3 N2 C8 118.5(7) . . . . ?
C5 C4 C3 C2 3.7(10) . . . . ?
S1 C4 C3 C2 -176.0(4) . . . . ?
C3 C4 C5 C6 -1.6(11) . . . . ?
S1 C4 C5 C6 178.2(4) . . . . ?
C4 C5 C6 C1 -1.5(9) . . . . ?
C2 C1 C6 C5 2.2(10) . . . . ?
C7 C1 C6 C5 -179.0(5) . . . . ?
C6 C1 C2 C3 0.1(12) . . . . ?
C7 C1 C2 C3 -178.7(4) . . . . ?
C4 C3 C2 C1 -2.9(10) . . . . ?
N2 N3 C14 C13 -155.8(6) . . . . ?
C9 N3 C14 C13 81.2(6) . . . . ?
N3 C14 C13 C12 -85.3(9) . . . . ?
C14 C13 C12 C11 63.9(7) . . . . ?
C13 C12 C11 C10 -68.4(8) . . . . ?
C12 C11 C10 C9 86.7(11) . . . . ?
N2 N3 C9 C10 -146.6(7) . . . . ?
C14 N3 C9 C10 -23.6(6) . . . . ?
C11 C10 C9 N3 -50.3(8) . . . . ?

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
N1 H1 O1 0.86 2.04 2.788(7) 145.1 2_676
N2 H2 O3 0.86 1.92 2.751(5) 160.9 2_566

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_403GPa
_database_code_depnum_ccdc_archive 'CCDC 1495208'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8202(3)
_cell_length_b                   8.536(5)
_cell_length_c                   12.7885(14)
_cell_angle_alpha                80.81(2)
_cell_angle_beta                 85.069(6)
_cell_angle_gamma                85.606(14)
_cell_volume                     623.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    799
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       4030000
_cell_measurement_theta_min      1.6460
_cell_measurement_theta_max      26.6070
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.1098
_diffrn_reflns_Laue_measured_fraction_full 0.335
_diffrn_reflns_Laue_measured_fraction_max 0.329
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3065
_diffrn_reflns_point_group_measured_fraction_full 0.335
_diffrn_reflns_point_group_measured_fraction_max 0.329
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         4030000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.335
_diffrn_measured_fraction_theta_max 0.329
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                552
_reflns_number_total             839
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         839
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.0762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1356
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0208(3) 0.2497(6) 0.21753(14) 0.0312(18) Uani 1 1 d . U . . .
O3 O -0.0669(7) 0.4477(14) 0.3788(4) 0.036(4) Uani 1 1 d . U . . .
O2 O -0.2253(6) 0.2485(13) 0.2330(3) 0.038(6) Uani 1 1 d . U . . .
C8 C 0.0661(10) 0.336(2) 0.4029(5) 0.0307(19) Uani 1 1 d . U . . .
N2 N 0.1567(7) 0.3038(16) 0.4979(4) 0.0309(19) Uani 1 1 d . U . . .
H2 H 0.1119 0.3588 0.5476 0.037 Uiso 1 1 calc R . . . .
C4 C 0.0918(9) 0.441(2) 0.1566(5) 0.034(3) Uani 1 1 d . U . . .
N1 N 0.1279(8) 0.2314(17) 0.3343(4) 0.0311(19) Uani 1 1 d . U . . .
H1 H 0.2261 0.1533 0.3523 0.037 Uiso 1 1 calc R . . . .
O1 O 0.1513(8) 0.1319(15) 0.1648(4) 0.038(3) Uani 1 1 d . U . . .
N3 N 0.3281(8) 0.1771(16) 0.5136(4) 0.0313(19) Uani 1 1 d . U . . .
C3 C 0.3189(10) 0.469(2) 0.1271(5) 0.034(3) Uani 1 1 d . U . . .
H3 H 0.4361 0.3923 0.1457 0.041 Uiso 1 1 calc R . . . .
C6 C -0.0269(10) 0.698(2) 0.0737(5) 0.034(3) Uani 1 1 d . U . . .
H6 H -0.1459 0.7735 0.0552 0.041 Uiso 1 1 calc R . . . .
C5 C -0.0815(9) 0.555(2) 0.1314(5) 0.034(3) Uani 1 1 d . U . . .
H5 H -0.2345 0.5349 0.1531 0.041 Uiso 1 1 calc R . . . .
C14 C 0.2627(10) 0.071(2) 0.6124(5) 0.0318(19) Uani 1 1 d . U . . .
H14A H 0.3772 -0.0184 0.6209 0.038 Uiso 1 1 calc R . . . .
H14B H 0.1161 0.0283 0.6047 0.038 Uiso 1 1 calc R . . . .
C1 C 0.2001(9) 0.734(2) 0.0416(5) 0.034(3) Uani 1 1 d . U . . .
C2 C 0.3680(10) 0.612(2) 0.0707(5) 0.034(3) Uani 1 1 d . U . . .
H2A H 0.5220 0.6295 0.0498 0.041 Uiso 1 1 calc R . . . .
C9 C 0.5554(9) 0.2405(18) 0.5102(5) 0.0320(19) Uani 1 1 d D U . . .
H9A H 0.5821 0.3077 0.4422 0.038 Uiso 1 1 calc R . . . .
H9B H 0.6708 0.1521 0.5128 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2676(10) 0.889(2) -0.0156(5) 0.036(6) Uani 1 1 d . U . . .
H7A H 0.1558 0.9310 -0.0655 0.054 Uiso 1 1 calc GR . . . .
H7B H 0.4166 0.8765 -0.0527 0.054 Uiso 1 1 calc GR . . . .
H7C H 0.2745 0.9616 0.0342 0.054 Uiso 1 1 calc GR . . . .
C13 C 0.2406(10) 0.146(2) 0.7134(5) 0.032(2) Uani 1 1 d . U . . .
H13A H 0.1824 0.2557 0.6967 0.038 Uiso 1 1 calc R . . . .
H13B H 0.1288 0.0907 0.7640 0.038 Uiso 1 1 calc R . . . .
C12 C 0.4673(9) 0.1402(19) 0.7641(5) 0.032(2) Uani 1 1 d D U . . .
H12A H 0.5209 0.0296 0.7825 0.039 Uiso 1 1 calc R . . . .
H12B H 0.4377 0.1838 0.8299 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6628(9) 0.2281(18) 0.6978(5) 0.033(2) Uani 1 1 d D U . . .
H11A H 0.7298 0.2923 0.7420 0.039 Uiso 1 1 calc R . . . .
H11B H 0.7822 0.1499 0.6785 0.039 Uiso 1 1 calc R . . . .
C10 C 0.5952(10) 0.3355(18) 0.5967(5) 0.033(2) Uani 1 1 d D U . . .
H10A H 0.4552 0.3994 0.6124 0.039 Uiso 1 1 calc R . . . .
H10B H 0.7167 0.4070 0.5715 0.039 Uiso 1 1 calc R . . . .


_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
S1 O2 1.430(4) . ?
S1 C4 1.759(15) . ?
S1 N1 1.647(5) . ?
S1 O1 1.433(12) . ?
O3 C8 1.200(15) . ?
C8 N2 1.346(7) . ?
C8 N1 1.36(2) . ?
N2 H2 0.8600 . ?
N2 N3 1.416(14) . ?
C4 C3 1.371(8) . ?
C4 C5 1.365(16) . ?
N1 H1 0.8600 . ?
N3 C14 1.473(10) . ?
N3 C9 1.462(10) . ?
C3 H3 0.9300 . ?
C3 C2 1.346(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.366(18) . ?
C6 C1 1.393(8) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.523(18) . ?
C1 C2 1.405(17) . ?
C1 C7 1.469(18) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.514(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.514(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.529(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.524(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 108.2(5) . . ?
O2 S1 N1 108.8(3) . . ?
O2 S1 O1 120.4(6) . . ?
N1 S1 C4 103.3(6) . . ?
O1 S1 C4 110.2(5) . . ?
O1 S1 N1 104.6(5) . . ?
O3 C8 N2 123.1(14) . . ?
O3 C8 N1 120.3(7) . . ?
N2 C8 N1 116.5(12) . . ?
C8 N2 H2 121.0 . . ?
C8 N2 N3 118.0(11) . . ?
N3 N2 H2 121.0 . . ?
C3 C4 S1 119.1(10) . . ?
C5 C4 S1 119.2(6) . . ?
C5 C4 C3 121.4(11) . . ?
S1 N1 H1 119.0 . . ?
C8 N1 S1 122.1(8) . . ?
C8 N1 H1 119.0 . . ?
N2 N3 C14 108.9(6) . . ?
N2 N3 C9 109.8(11) . . ?
C9 N3 C14 114.6(4) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 C4 118.4(10) . . ?
C2 C3 H3 120.8 . . ?
C5 C6 H6 118.7 . . ?
C5 C6 C1 122.5(10) . . ?
C1 C6 H6 118.7 . . ?
C4 C5 C6 119.1(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N3 C14 H14A 108.4 . . ?
N3 C14 H14B 108.4 . . ?
N3 C14 C13 115.7(13) . . ?
H14A C14 H14B 107.4 . . ?
C13 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
C6 C1 C2 114.9(11) . . ?
C6 C1 C7 124.4(10) . . ?
C2 C1 C7 120.7(6) . . ?
C3 C2 C1 123.8(6) . . ?
C3 C2 H2A 118.1 . . ?
C1 C2 H2A 118.1 . . ?
N3 C9 H9A 108.1 . . ?
N3 C9 H9B 108.1 . . ?
N3 C9 C10 116.9(7) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 C14 112.9(9) . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C13 C12 C11 116.7(5) . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C10 C11 C12 115.9(5) . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C9 C10 C11 111.8(11) . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?

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
N2 H2 O3 0.86 2.02 2.831(18) 157.4 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 173.1(9) . . . . ?
S1 C4 C5 C6 -172.8(9) . . . . ?
O3 C8 N2 N3 -174.2(8) . . . . ?
O3 C8 N1 S1 -1.6(13) . . . . ?
O2 S1 C4 C3 -175.8(9) . . . . ?
O2 S1 C4 C5 -1.5(11) . . . . ?
O2 S1 N1 C8 -57.9(11) . . . . ?
C8 N2 N3 C14 -128.8(10) . . . . ?
C8 N2 N3 C9 105.0(9) . . . . ?
N2 C8 N1 S1 176.9(5) . . . . ?
N2 N3 C14 C13 -60.7(8) . . . . ?
N2 N3 C9 C10 64.4(9) . . . . ?
C4 S1 N1 C8 57.0(9) . . . . ?
C4 C3 C2 C1 1.1(18) . . . . ?
N1 S1 C4 C3 69.0(10) . . . . ?
N1 S1 C4 C5 -116.7(9) . . . . ?
N1 C8 N2 N3 7.4(12) . . . . ?
O1 S1 C4 C3 -42.3(9) . . . . ?
O1 S1 C4 C5 132.0(9) . . . . ?
O1 S1 N1 C8 172.3(8) . . . . ?
N3 C14 C13 C12 -87.3(11) . . . . ?
N3 C9 C10 C11 83.2(9) . . . . ?
C3 C4 C5 C6 1.3(18) . . . . ?
C6 C1 C2 C3 -1.4(17) . . . . ?
C5 C4 C3 C2 -1.1(18) . . . . ?
C5 C6 C1 C2 1.6(17) . . . . ?
C5 C6 C1 C7 -176.7(12) . . . . ?
C14 N3 C9 C10 -58.5(16) . . . . ?
C14 C13 C12 C11 61.5(18) . . . . ?
C1 C6 C5 C4 -1.6(18) . . . . ?
C9 N3 C14 C13 62.7(13) . . . . ?
C7 C1 C2 C3 177.0(11) . . . . ?
C13 C12 C11 C10 10.5(19) . . . . ?
C12 C11 C10 C9 -74.8(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6p10GPA
_database_code_depnum_ccdc_archive 'CCDC 1493077'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_6p10GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.343 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.7694(3)
_cell_length_b                   8.1369(4)
_cell_length_c                   12.941(3)
_cell_angle_alpha                82.207(9)
_cell_angle_beta                 87.842(9)
_cell_angle_gamma                82.147(4)
_cell_volume                     596.16(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    926
_cell_measurement_theta_min      2.5430
_cell_measurement_theta_max      27.2320

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         6100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3006
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.338
_diffrn_measured_fraction_theta_full 0.343
_diffrn_reflns_Laue_measured_fraction_max 0.338
_diffrn_reflns_Laue_measured_fraction_full 0.343
_diffrn_reflns_point_group_measured_fraction_max 0.338
_diffrn_reflns_point_group_measured_fraction_full 0.343
_reflns_number_total             824
_reflns_number_gt                629
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         824
_refine_ls_number_parameters     191
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      0.947
_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
S1 S 0.22452(17) 0.99947(14) 0.3891(3) 0.0166(19) Uani 1 1 d . U . . .
O3 O 0.0384(5) 0.6788(4) 0.4109(7) 0.018(3) Uani 1 1 d . U . . .
N1 N 0.2583(5) 0.8453(4) 0.4810(8) 0.018(3) Uani 1 1 d . U . . .
H1 H 0.3479 0.8522 0.5314 0.021 Uiso 1 1 calc R U . . .
N3 N 0.3162(6) 0.6331(4) 0.6518(9) 0.015(3) Uani 1 1 d . U . . .
C4 C 0.4013(8) 0.9332(7) 0.2877(13) 0.016(3) Uani 1 1 d . U . . .
O2 O -0.0087(4) 1.0315(3) 0.3545(6) 0.017(3) Uani 1 1 d . U . . .
O1 O 0.3199(4) 1.1317(4) 0.4290(7) 0.017(4) Uani 1 1 d . U . . .
C8 C 0.1524(8) 0.7017(6) 0.4845(12) 0.011(3) Uani 1 1 d . U . . .
N2 N 0.1990(7) 0.5935(6) 0.5678(10) 0.020(3) Uani 1 1 d . U . . .
H2 H 0.1566 0.4956 0.5709 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6316(7) 0.8655(5) 0.3107(10) 0.018(3) Uani 1 1 d . U . . .
H3 H 0.6856 0.8499 0.3786 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6999(9) 0.8393(7) 0.1300(14) 0.019(4) Uani 1 1 d . U . . .
C5 C 0.3183(9) 0.9511(7) 0.1875(13) 0.018(3) Uani 1 1 d . U . . .
H5 H 0.1641 0.9964 0.1733 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4640(7) 0.9020(5) 0.1111(11) 0.018(3) Uani 1 1 d . U . . .
H6 H 0.4077 0.9096 0.0440 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7763(9) 0.8223(7) 0.2283(14) 0.017(4) Uani 1 1 d . U . . .
H2A H 0.9320 0.7800 0.2413 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1594(7) 0.6238(6) 0.7446(11) 0.017(3) Uani 1 1 d . U . . .
H14A H 0.1674 0.5081 0.7761 0.021 Uiso 1 1 calc R U . . .
H14B H -0.0003 0.6615 0.7229 0.021 Uiso 1 1 calc R U . . .
C7 C 0.8658(7) 0.7874(6) 0.0431(11) 0.024(4) Uani 1 1 d . U . . .
H7A H 0.9870 0.8583 0.0335 0.036 Uiso 1 1 calc R U . . .
H7B H 0.7810 0.7977 -0.0204 0.036 Uiso 1 1 calc R U . . .
H7C H 0.9345 0.6733 0.0611 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2198(7) 0.7274(6) 0.8246(10) 0.021(3) Uani 1 1 d . U . . .
H13A H 0.0798 0.7581 0.8653 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2691 0.8299 0.7889 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4102(7) 0.6420(6) 0.8984(11) 0.024(4) Uani 1 1 d . U . . .
H12A H 0.3645 0.5380 0.9336 0.029 Uiso 1 1 calc R U . . .
H12B H 0.4296 0.7133 0.9510 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6423(7) 0.6056(6) 0.8399(11) 0.020(4) Uani 1 1 d . U . . .
H11A H 0.6778 0.7074 0.7978 0.024 Uiso 1 1 calc R U . . .
H11B H 0.7663 0.5699 0.8898 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6359(8) 0.4724(6) 0.7707(12) 0.016(4) Uani 1 1 d . U . . .
H10A H 0.5407 0.3914 0.8058 0.019 Uiso 1 1 calc R U . . .
H10B H 0.7937 0.4148 0.7651 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5457(8) 0.5243(6) 0.6618(12) 0.015(4) Uani 1 1 d . U . . .
H9A H 0.6614 0.5826 0.6211 0.018 Uiso 1 1 calc R U . . .
H9B H 0.5331 0.4238 0.6309 0.018 Uiso 1 1 calc R U . . .


_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
S1 O2 1.413(4) . ?
S1 O1 1.436(4) . ?
S1 N1 1.604(9) . ?
S1 C4 1.730(13) . ?
O3 C8 1.226(14) . ?
N1 C8 1.385(5) . ?
N1 H1 0.8600 . ?
N3 N2 1.397(14) . ?
N3 C14 1.476(15) . ?
N3 C9 1.488(6) . ?
C4 C5 1.38(2) . ?
C4 C3 1.393(7) . ?
C8 N2 1.308(17) . ?
N2 H2 0.8600 . ?
C3 C2 1.382(17) . ?
C3 H3 0.9300 . ?
C1 C2 1.35(3) . ?
C1 C6 1.405(7) . ?
C1 C7 1.516(17) . ?
C5 C6 1.340(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.500(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.514(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.527(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.501(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.51(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 117.98(18) . . ?
O2 S1 N1 111.4(3) . . ?
O1 S1 N1 104.6(4) . . ?
O2 S1 C4 108.0(5) . . ?
O1 S1 C4 109.4(3) . . ?
N1 S1 C4 104.7(4) . . ?
C8 N1 S1 124.2(8) . . ?
C8 N1 H1 117.9 . . ?
S1 N1 H1 117.9 . . ?
N2 N3 C14 108.6(5) . . ?
N2 N3 C9 108.5(7) . . ?
C14 N3 C9 116.2(9) . . ?
C5 C4 C3 121.5(12) . . ?
C5 C4 S1 121.0(5) . . ?
C3 C4 S1 117.4(11) . . ?
O3 C8 N2 124.9(5) . . ?
O3 C8 N1 120.8(11) . . ?
N2 C8 N1 114.2(9) . . ?
C8 N2 N3 121.6(5) . . ?
C8 N2 H2 119.2 . . ?
N3 N2 H2 119.2 . . ?
C2 C3 C4 117.2(12) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C2 C1 C6 118.5(13) . . ?
C2 C1 C7 120.0(7) . . ?
C6 C1 C7 121.5(13) . . ?
C6 C5 C4 118.8(6) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 121.6(13) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C1 C2 C3 122.3(7) . . ?
C1 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
N3 C14 C13 113.0(5) . . ?
N3 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 114.6(4) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C12 C11 111.1(10) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C10 C11 C12 112.0(5) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C10 C9 118.3(6) . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10B 107.7 . . ?
C9 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
N3 C9 C10 116.6(11) . . ?
N3 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
N3 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 38.8(7) . . . . ?
O1 S1 N1 C8 167.3(5) . . . . ?
C4 S1 N1 C8 -77.7(6) . . . . ?
O2 S1 C4 C5 13.2(7) . . . . ?
O1 S1 C4 C5 -116.4(6) . . . . ?
N1 S1 C4 C5 132.1(6) . . . . ?
O2 S1 C4 C3 -168.5(4) . . . . ?
O1 S1 C4 C3 62.0(6) . . . . ?
N1 S1 C4 C3 -49.6(5) . . . . ?
S1 N1 C8 O3 6.0(9) . . . . ?
S1 N1 C8 N2 -178.3(6) . . . . ?
O3 C8 N2 N3 -175.4(7) . . . . ?
N1 C8 N2 N3 9.1(10) . . . . ?
C14 N3 N2 C8 117.6(7) . . . . ?
C9 N3 N2 C8 -115.3(8) . . . . ?
C5 C4 C3 C2 2.3(9) . . . . ?
S1 C4 C3 C2 -176.1(4) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
S1 C4 C5 C6 178.2(3) . . . . ?
C4 C5 C6 C1 -2.5(9) . . . . ?
C2 C1 C6 C5 2.8(10) . . . . ?
C7 C1 C6 C5 -178.6(5) . . . . ?
C6 C1 C2 C3 -0.5(11) . . . . ?
C7 C1 C2 C3 -179.1(4) . . . . ?
C4 C3 C2 C1 -1.9(9) . . . . ?
N2 N3 C14 C13 -156.4(6) . . . . ?
C9 N3 C14 C13 81.0(6) . . . . ?
N3 C14 C13 C12 -84.2(9) . . . . ?
C14 C13 C12 C11 63.8(7) . . . . ?
C13 C12 C11 C10 -69.1(8) . . . . ?
C12 C11 C10 C9 86.7(10) . . . . ?
N2 N3 C9 C10 -146.5(6) . . . . ?
C14 N3 C9 C10 -23.9(6) . . . . ?
C11 C10 C9 N3 -50.4(8) . . . . ?

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
N1 H1 O1 0.86 2.03 2.777(7) 145.0 2_676
N2 H2 O3 0.86 1.91 2.738(5) 160.2 2_566

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_3p32GPA
_database_code_depnum_ccdc_archive 'CCDC 1493073'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3p32GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.341 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.9272(3)
_cell_length_b                   8.3697(4)
_cell_length_c                   13.124(2)
_cell_angle_alpha                81.580(8)
_cell_angle_beta                 87.185(8)
_cell_angle_gamma                82.254(4)
_cell_volume                     637.89(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    942
_cell_measurement_theta_min      2.4750
_cell_measurement_theta_max      26.5970

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         3320000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3135
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.332
_diffrn_measured_fraction_theta_full 0.341
_diffrn_reflns_Laue_measured_fraction_max 0.332
_diffrn_reflns_Laue_measured_fraction_full 0.341
_diffrn_reflns_point_group_measured_fraction_max 0.332
_diffrn_reflns_point_group_measured_fraction_full 0.341
_reflns_number_total             869
_reflns_number_gt                642
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         869
_refine_ls_number_parameters     191
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      0.992
_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
S1 S 0.23267(15) 0.99168(13) 0.3906(2) 0.0170(17) Uani 1 1 d . U . . .
O3 O 0.0463(5) 0.6765(3) 0.4152(6) 0.018(3) Uani 1 1 d . U . . .
N1 N 0.2576(5) 0.8406(4) 0.4819(7) 0.021(2) Uani 1 1 d . U . . .
H1 H 0.3410 0.8473 0.5325 0.025 Uiso 1 1 calc R U . . .
N3 N 0.3103(5) 0.6329(4) 0.6525(8) 0.014(3) Uani 1 1 d . U . . .
C4 C 0.4073(8) 0.9282(7) 0.2889(12) 0.019(2) Uani 1 1 d . U . . .
O2 O 0.0071(4) 1.0244(3) 0.3566(5) 0.021(3) Uani 1 1 d . U . . .
O1 O 0.3291(4) 1.1188(3) 0.4292(6) 0.021(3) Uani 1 1 d . U . . .
C8 C 0.1556(7) 0.7010(6) 0.4855(11) 0.014(3) Uani 1 1 d . U . . .
N2 N 0.1952(6) 0.5948(5) 0.5690(9) 0.016(2) Uani 1 1 d . U . . .
H2 H 0.1503 0.5005 0.5730 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6346(6) 0.8640(5) 0.3124(10) 0.018(3) Uani 1 1 d . U . . .
H3 H 0.6864 0.8512 0.3793 0.022 Uiso 1 1 calc R U . . .
C1 C 0.7019(8) 0.8374(7) 0.1304(13) 0.018(3) Uani 1 1 d . U . . .
C5 C 0.3312(8) 0.9453(7) 0.1907(12) 0.019(2) Uani 1 1 d . U . . .
H5 H 0.1818 0.9896 0.1764 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4735(6) 0.8977(5) 0.1155(10) 0.021(3) Uani 1 1 d . U . . .
H6 H 0.4170 0.9052 0.0498 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7756(8) 0.8212(7) 0.2316(13) 0.018(4) Uani 1 1 d . U . . .
H2A H 0.9265 0.7798 0.2448 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1569(7) 0.6250(6) 0.7449(10) 0.017(3) Uani 1 1 d . U . . .
H14A H 0.1633 0.5126 0.7771 0.020 Uiso 1 1 calc R U . . .
H14B H 0.0017 0.6621 0.7240 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8624(7) 0.7894(6) 0.0456(10) 0.027(4) Uani 1 1 d . U . . .
H7A H 0.9579 0.8732 0.0248 0.040 Uiso 1 1 calc R U . . .
H7B H 0.7772 0.7751 -0.0121 0.040 Uiso 1 1 calc R U . . .
H7C H 0.9554 0.6891 0.0694 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2187(6) 0.7280(5) 0.8235(9) 0.019(3) Uani 1 1 d . U . . .
H13A H 0.2623 0.8288 0.7866 0.022 Uiso 1 1 calc R U . . .
H13B H 0.0835 0.7558 0.8653 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4057(6) 0.6508(6) 0.8937(10) 0.022(3) Uani 1 1 d . U . . .
H12A H 0.3632 0.5504 0.9318 0.027 Uiso 1 1 calc R U . . .
H12B H 0.4254 0.7232 0.9430 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6325(6) 0.6135(6) 0.8344(10) 0.022(4) Uani 1 1 d . U . . .
H11A H 0.6672 0.7117 0.7909 0.026 Uiso 1 1 calc R U . . .
H11B H 0.7535 0.5801 0.8832 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6254(7) 0.4822(6) 0.7690(11) 0.019(4) Uani 1 1 d . U . . .
H10A H 0.5334 0.4036 0.8059 0.023 Uiso 1 1 calc R U . . .
H10B H 0.7790 0.4266 0.7631 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5347(7) 0.5299(6) 0.6602(11) 0.016(3) Uani 1 1 d . U . . .
H9A H 0.6452 0.5875 0.6180 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5230 0.4311 0.6315 0.020 Uiso 1 1 calc R U . . .


_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
S1 O2 1.409(3) . ?
S1 O1 1.437(3) . ?
S1 N1 1.606(8) . ?
S1 C4 1.749(13) . ?
O3 C8 1.210(13) . ?
N1 C8 1.380(5) . ?
N1 H1 0.8600 . ?
N3 N2 1.415(13) . ?
N3 C14 1.479(14) . ?
N3 C9 1.483(5) . ?
C4 C5 1.37(2) . ?
C4 C3 1.413(7) . ?
C8 N2 1.315(16) . ?
N2 H2 0.8600 . ?
C3 C2 1.377(16) . ?
C3 H3 0.9300 . ?
C1 C6 1.393(6) . ?
C1 C2 1.40(2) . ?
C1 C7 1.493(16) . ?
C5 C6 1.337(15) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.524(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.492(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.538(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.496(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.53(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 118.46(16) . . ?
O2 S1 N1 110.6(2) . . ?
O1 S1 N1 105.1(4) . . ?
O2 S1 C4 107.8(4) . . ?
O1 S1 C4 108.6(3) . . ?
N1 S1 C4 105.6(4) . . ?
C8 N1 S1 125.2(7) . . ?
C8 N1 H1 117.4 . . ?
S1 N1 H1 117.4 . . ?
N2 N3 C14 109.0(5) . . ?
N2 N3 C9 108.4(6) . . ?
C14 N3 C9 117.5(9) . . ?
C5 C4 C3 121.5(11) . . ?
C5 C4 S1 122.0(5) . . ?
C3 C4 S1 116.5(10) . . ?
O3 C8 N2 123.1(6) . . ?
O3 C8 N1 122.1(11) . . ?
N2 C8 N1 114.7(9) . . ?
C8 N2 N3 121.2(5) . . ?
C8 N2 H2 119.4 . . ?
N3 N2 H2 119.4 . . ?
C2 C3 C4 116.7(11) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C6 C1 C2 116.0(12) . . ?
C6 C1 C7 123.2(12) . . ?
C2 C1 C7 120.7(6) . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 123.3(11) . . ?
C5 C6 H6 118.3 . . ?
C1 C6 H6 118.3 . . ?
C3 C2 C1 122.9(6) . . ?
C3 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
N3 C14 C13 112.7(4) . . ?
N3 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 C14 115.7(4) . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C13 C12 C11 112.1(9) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C10 C11 C12 112.1(4) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C10 C9 118.5(6) . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10B 107.7 . . ?
C9 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
N3 C9 C10 115.6(10) . . ?
N3 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
N3 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 40.1(6) . . . . ?
O1 S1 N1 C8 169.1(5) . . . . ?
C4 S1 N1 C8 -76.2(6) . . . . ?
O2 S1 C4 C5 12.5(7) . . . . ?
O1 S1 C4 C5 -117.0(7) . . . . ?
N1 S1 C4 C5 130.7(7) . . . . ?
O2 S1 C4 C3 -170.0(4) . . . . ?
O1 S1 C4 C3 60.5(5) . . . . ?
N1 S1 C4 C3 -51.7(5) . . . . ?
S1 N1 C8 O3 4.5(9) . . . . ?
S1 N1 C8 N2 -178.4(5) . . . . ?
O3 C8 N2 N3 -175.6(6) . . . . ?
N1 C8 N2 N3 7.3(10) . . . . ?
C14 N3 N2 C8 118.5(7) . . . . ?
C9 N3 N2 C8 -112.5(7) . . . . ?
C5 C4 C3 C2 0.6(9) . . . . ?
S1 C4 C3 C2 -176.9(4) . . . . ?
C3 C4 C5 C6 1.2(11) . . . . ?
S1 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C1 -3.1(9) . . . . ?
C2 C1 C6 C5 2.9(9) . . . . ?
C7 C1 C6 C5 -177.9(5) . . . . ?
C4 C3 C2 C1 -0.7(9) . . . . ?
C6 C1 C2 C3 -1.0(11) . . . . ?
C7 C1 C2 C3 179.9(4) . . . . ?
N2 N3 C14 C13 -156.1(5) . . . . ?
C9 N3 C14 C13 80.2(5) . . . . ?
N3 C14 C13 C12 -82.3(9) . . . . ?
C14 C13 C12 C11 62.2(7) . . . . ?
C13 C12 C11 C10 -68.0(8) . . . . ?
C12 C11 C10 C9 86.4(10) . . . . ?
N2 N3 C9 C10 -148.3(6) . . . . ?
C14 N3 C9 C10 -24.2(6) . . . . ?
C11 C10 C9 N3 -51.0(8) . . . . ?

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
N1 H1 O1 0.86 2.11 2.846(6) 143.5 2_676
N2 H2 O3 0.86 1.99 2.821(4) 162.4 2_566

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_213GPa
_database_code_depnum_ccdc_archive 'CCDC 1495205'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9669(3)
_cell_length_b                   8.6945(18)
_cell_length_c                   12.9785(9)
_cell_angle_alpha                80.432(10)
_cell_angle_beta                 85.884(5)
_cell_angle_gamma                85.774(8)
_cell_volume                     660.93(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    792
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       2130000
_cell_measurement_theta_min      1.6130
_cell_measurement_theta_max      24.9840
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1332
_diffrn_reflns_av_unetI/netI     0.1253
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.333
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3287
_diffrn_reflns_point_group_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         1.594
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         2130000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.344
_diffrn_measured_fraction_theta_max 0.333
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                525
_reflns_number_total             900
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         900
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0220(3) 0.2543(6) 0.2191(2) 0.042(2) Uani 1 1 d . U . . .
O3 O -0.0679(8) 0.4505(15) 0.3793(5) 0.049(5) Uani 1 1 d . U . . .
O2 O -0.2189(7) 0.2542(13) 0.2325(5) 0.029(7) Uani 1 1 d . U . . .
C8 C 0.0634(12) 0.334(2) 0.4011(8) 0.043(2) Uani 1 1 d . U . . .
N2 N 0.1589(8) 0.3085(17) 0.4964(6) 0.044(2) Uani 1 1 d . U . . .
H2 H 0.1230 0.3660 0.5437 0.052 Uiso 1 1 calc R . . . .
C4 C 0.0908(10) 0.441(2) 0.1577(7) 0.043(3) Uani 1 1 d . U . . .
N1 N 0.1249(9) 0.2359(19) 0.3365(6) 0.043(2) Uani 1 1 d . U . . .
H1 H 0.2214 0.1597 0.3553 0.052 Uiso 1 1 calc R . . . .
O1 O 0.1519(8) 0.1405(15) 0.1707(6) 0.051(4) Uani 1 1 d . U . . .
N3 N 0.3258(9) 0.1765(17) 0.5111(6) 0.044(2) Uani 1 1 d . U . . .
C3 C 0.3145(10) 0.465(2) 0.1257(7) 0.044(3) Uani 1 1 d . U . . .
H3 H 0.4265 0.3852 0.1398 0.053 Uiso 1 1 calc R . . . .
C6 C -0.0191(10) 0.6979(19) 0.0768(7) 0.043(3) Uani 1 1 d . U . . .
H6 H -0.1330 0.7750 0.0601 0.052 Uiso 1 1 calc R . . . .
C5 C -0.0758(10) 0.556(2) 0.1326(8) 0.043(3) Uani 1 1 d . U . . .
H5 H -0.2254 0.5380 0.1531 0.052 Uiso 1 1 calc R . . . .
C14 C 0.2604(12) 0.079(2) 0.6093(7) 0.044(2) Uani 1 1 d . U . . .
H14A H 0.3689 -0.0101 0.6189 0.053 Uiso 1 1 calc R . . . .
H14B H 0.1165 0.0391 0.6008 0.053 Uiso 1 1 calc R . . . .
C1 C 0.2016(10) 0.730(2) 0.0445(7) 0.043(3) Uani 1 1 d . U . . .
C2 C 0.3640(10) 0.608(2) 0.0731(7) 0.044(3) Uani 1 1 d . U . . .
H2A H 0.5144 0.6259 0.0549 0.052 Uiso 1 1 calc R . . . .
C9 C 0.5497(11) 0.2400(18) 0.5096(7) 0.044(2) Uani 1 1 d D U . . .
H9A H 0.5710 0.3119 0.4445 0.053 Uiso 1 1 calc R . . . .
H9B H 0.6625 0.1541 0.5079 0.053 Uiso 1 1 calc R . . . .
C7 C 0.2662(11) 0.884(2) -0.0105(8) 0.061(8) Uani 1 1 d . U . . .
H7A H 0.1589 0.9250 -0.0614 0.092 Uiso 1 1 calc GR . . . .
H7B H 0.4129 0.8736 -0.0451 0.092 Uiso 1 1 calc GR . . . .
H7C H 0.2690 0.9546 0.0390 0.092 Uiso 1 1 calc GR . . . .
C13 C 0.2382(11) 0.148(2) 0.7127(7) 0.044(2) Uani 1 1 d . U . . .
H13A H 0.1830 0.2570 0.6982 0.053 Uiso 1 1 calc R . . . .
H13B H 0.1298 0.0922 0.7613 0.053 Uiso 1 1 calc R . . . .
C12 C 0.4593(10) 0.137(2) 0.7614(7) 0.044(2) Uani 1 1 d D U . . .
H12A H 0.5060 0.0272 0.7793 0.053 Uiso 1 1 calc R . . . .
H12B H 0.4350 0.1786 0.8265 0.053 Uiso 1 1 calc R . . . .
C11 C 0.6526(10) 0.2182(19) 0.6988(7) 0.045(2) Uani 1 1 d D U . . .
H11A H 0.7663 0.1388 0.6825 0.053 Uiso 1 1 calc R . . . .
H11B H 0.7190 0.2801 0.7429 0.053 Uiso 1 1 calc R . . . .
C10 C 0.5971(11) 0.3234(17) 0.5978(7) 0.045(2) Uani 1 1 d D U . . .
H10A H 0.4665 0.3918 0.6117 0.054 Uiso 1 1 calc R . . . .
H10B H 0.7221 0.3887 0.5750 0.054 Uiso 1 1 calc R . . . .


_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
S1 O2 1.435(4) . ?
S1 C4 1.748(14) . ?
S1 N1 1.662(9) . ?
S1 O1 1.413(14) . ?
O3 C8 1.241(17) . ?
C8 N2 1.377(11) . ?
C8 N1 1.31(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.460(15) . ?
C4 C3 1.389(8) . ?
C4 C5 1.373(16) . ?
N1 H1 0.8600 . ?
N3 C14 1.453(8) . ?
N3 C9 1.480(11) . ?
C3 H3 0.9300 . ?
C3 C2 1.359(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.375(17) . ?
C6 C1 1.387(8) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.55(2) . ?
C1 C2 1.407(16) . ?
C1 C7 1.473(19) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(17) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.493(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.510(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.512(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 107.8(5) . . ?
O2 S1 N1 108.4(4) . . ?
N1 S1 C4 104.1(7) . . ?
O1 S1 O2 121.9(8) . . ?
O1 S1 C4 109.5(6) . . ?
O1 S1 N1 103.6(6) . . ?
O3 C8 N2 118.9(17) . . ?
O3 C8 N1 123.6(9) . . ?
N1 C8 N2 117.4(13) . . ?
C8 N2 H2 122.6 . . ?
C8 N2 N3 114.9(14) . . ?
N3 N2 H2 122.6 . . ?
C3 C4 S1 118.3(10) . . ?
C5 C4 S1 120.3(6) . . ?
C5 C4 C3 121.0(10) . . ?
S1 N1 H1 119.0 . . ?
C8 N1 S1 121.9(9) . . ?
C8 N1 H1 119.0 . . ?
N2 N3 C9 107.8(11) . . ?
C14 N3 N2 106.8(8) . . ?
C14 N3 C9 113.9(6) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 C4 117.7(11) . . ?
C2 C3 H3 121.1 . . ?
C5 C6 H6 118.7 . . ?
C5 C6 C1 122.5(10) . . ?
C1 C6 H6 118.7 . . ?
C4 C5 C6 119.3(7) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N3 C14 H14A 107.3 . . ?
N3 C14 H14B 107.3 . . ?
N3 C14 C13 120.0(15) . . ?
H14A C14 H14B 106.9 . . ?
C13 C14 H14A 107.3 . . ?
C13 C14 H14B 107.3 . . ?
C6 C1 C2 115.3(10) . . ?
C6 C1 C7 123.1(11) . . ?
C2 C1 C7 121.5(7) . . ?
C3 C2 C1 124.0(7) . . ?
C3 C2 H2A 118.0 . . ?
C1 C2 H2A 118.0 . . ?
N3 C9 H9A 107.8 . . ?
N3 C9 H9B 107.8 . . ?
N3 C9 C10 118.1(8) . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.8 . . ?
C10 C9 H9B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 C14 111.2(10) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C13 C12 H12A 107.8 . . ?
C13 C12 H12B 107.8 . . ?
C13 C12 C11 118.1(5) . . ?
H12A C12 H12B 107.1 . . ?
C11 C12 H12A 107.8 . . ?
C11 C12 H12B 107.8 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C12 C11 C10 116.6(5) . . ?
H11A C11 H11B 107.3 . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C9 C10 C11 115.1(12) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?

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
N2 H2 O3 0.86 2.01 2.85(2) 163.4 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 176.5(11) . . . . ?
S1 C4 C5 C6 -174.7(12) . . . . ?
O3 C8 N2 N3 -174.8(8) . . . . ?
O3 C8 N1 S1 -2.9(18) . . . . ?
O2 S1 C4 C3 -172.9(11) . . . . ?
O2 S1 C4 C5 0.6(15) . . . . ?
O2 S1 N1 C8 -56.7(14) . . . . ?
C8 N2 N3 C14 -127.7(11) . . . . ?
C8 N2 N3 C9 109.5(9) . . . . ?
N2 C8 N1 S1 -179.9(5) . . . . ?
N2 N3 C14 C13 -58.5(10) . . . . ?
N2 N3 C9 C10 66.8(9) . . . . ?
C4 S1 N1 C8 57.9(11) . . . . ?
C4 C3 C2 C1 -3(2) . . . . ?
N1 S1 C4 C3 72.1(13) . . . . ?
N1 S1 C4 C5 -114.4(12) . . . . ?
N1 C8 N2 N3 2.3(14) . . . . ?
O1 S1 C4 C3 -38.2(13) . . . . ?
O1 S1 C4 C5 135.3(12) . . . . ?
O1 S1 N1 C8 172.5(11) . . . . ?
N3 C14 C13 C12 -86.6(11) . . . . ?
N3 C9 C10 C11 78.2(10) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
C5 C4 C3 C2 3(2) . . . . ?
C5 C6 C1 C2 0(2) . . . . ?
C5 C6 C1 C7 -176.8(14) . . . . ?
C14 N3 C9 C10 -51.5(17) . . . . ?
C14 C13 C12 C11 59.5(19) . . . . ?
C1 C6 C5 C4 0(2) . . . . ?
C9 N3 C14 C13 60.4(13) . . . . ?
C7 C1 C2 C3 178.7(15) . . . . ?
C13 C12 C11 C10 8(2) . . . . ?
C12 C11 C10 C9 -73.2(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_133GPa
_database_code_depnum_ccdc_archive 'CCDC 1495204'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0542(6)
_cell_length_b                   8.807(3)
_cell_length_c                   13.095(2)
_cell_angle_alpha                80.05(2)
_cell_angle_beta                 86.260(11)
_cell_angle_gamma                85.728(19)
_cell_volume                     684.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    788
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       1330000
_cell_measurement_theta_min      1.6040
_cell_measurement_theta_max      26.6540
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1468
_diffrn_reflns_av_unetI/netI     0.1344
_diffrn_reflns_Laue_measured_fraction_full 0.336
_diffrn_reflns_Laue_measured_fraction_max 0.325
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3323
_diffrn_reflns_point_group_measured_fraction_full 0.336
_diffrn_reflns_point_group_measured_fraction_max 0.325
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.581
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1330000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.336
_diffrn_measured_fraction_theta_max 0.325
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                469
_reflns_number_total             910
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         910
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0966P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.2213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0233(4) 0.2572(8) 0.2203(2) 0.058(2) Uani 1 1 d . U . . .
O3 O -0.0684(8) 0.4562(19) 0.3804(6) 0.065(5) Uani 1 1 d . U . . .
O2 O -0.2116(8) 0.2558(17) 0.2318(6) 0.054(9) Uani 1 1 d . U . . .
C8 C 0.0658(14) 0.338(3) 0.4012(9) 0.058(3) Uani 1 1 d . U . . .
N2 N 0.1635(10) 0.314(2) 0.4948(6) 0.058(3) Uani 1 1 d . U . . .
H2 H 0.1297 0.3727 0.5404 0.070 Uiso 1 1 calc R . . . .
C4 C 0.0946(12) 0.441(3) 0.1580(8) 0.056(3) Uani 1 1 d . U . . .
N1 N 0.1199(11) 0.238(2) 0.3362(7) 0.058(3) Uani 1 1 d . U . . .
H1 H 0.2096 0.1593 0.3563 0.070 Uiso 1 1 calc R . . . .
O1 O 0.1507(10) 0.146(2) 0.1733(7) 0.067(4) Uani 1 1 d . U . . .
N3 N 0.3233(10) 0.188(2) 0.5120(7) 0.058(3) Uani 1 1 d . U . . .
C3 C 0.3144(12) 0.465(3) 0.1282(8) 0.057(3) Uani 1 1 d . U . . .
H3 H 0.4258 0.3881 0.1451 0.068 Uiso 1 1 calc R . . . .
C6 C -0.0150(12) 0.699(2) 0.0775(8) 0.057(3) Uani 1 1 d . U . . .
H6 H -0.1263 0.7767 0.0616 0.068 Uiso 1 1 calc R . . . .
C5 C -0.0699(12) 0.555(3) 0.1329(8) 0.056(3) Uani 1 1 d . U . . .
H5 H -0.2171 0.5360 0.1525 0.068 Uiso 1 1 calc R . . . .
C14 C 0.2588(14) 0.074(3) 0.6049(8) 0.058(3) Uani 1 1 d . U . . .
H14A H 0.3693 -0.0126 0.6128 0.070 Uiso 1 1 calc R . . . .
H14B H 0.1183 0.0341 0.5942 0.070 Uiso 1 1 calc R . . . .
C1 C 0.2044(12) 0.727(3) 0.0463(8) 0.057(3) Uani 1 1 d . U . . .
C2 C 0.3616(12) 0.603(3) 0.0747(8) 0.057(3) Uani 1 1 d . U . . .
H2A H 0.5095 0.6184 0.0546 0.068 Uiso 1 1 calc R . . . .
C9 C 0.5439(13) 0.247(2) 0.5129(7) 0.058(3) Uani 1 1 d D U . . .
H9A H 0.5663 0.3197 0.4491 0.070 Uiso 1 1 calc R . . . .
H9B H 0.6528 0.1609 0.5103 0.070 Uiso 1 1 calc R . . . .
C7 C 0.2626(14) 0.881(3) -0.0087(8) 0.058(8) Uani 1 1 d . U . . .
H7A H 0.1542 0.9209 -0.0586 0.087 Uiso 1 1 calc GR . . . .
H7B H 0.4062 0.8731 -0.0436 0.087 Uiso 1 1 calc GR . . . .
H7C H 0.2650 0.9503 0.0405 0.087 Uiso 1 1 calc GR . . . .
C13 C 0.2365(13) 0.146(3) 0.7083(8) 0.058(3) Uani 1 1 d . U . . .
H13A H 0.1796 0.2528 0.6921 0.070 Uiso 1 1 calc R . . . .
H13B H 0.1298 0.0907 0.7566 0.070 Uiso 1 1 calc R . . . .
C12 C 0.4543(11) 0.140(2) 0.7602(8) 0.058(3) Uani 1 1 d D U . . .
H12A H 0.4268 0.1873 0.8217 0.070 Uiso 1 1 calc R . . . .
H12B H 0.4997 0.0320 0.7833 0.070 Uiso 1 1 calc R . . . .
C11 C 0.6468(12) 0.215(2) 0.6973(8) 0.059(3) Uani 1 1 d D U . . .
H11A H 0.7201 0.2713 0.7414 0.070 Uiso 1 1 calc R . . . .
H11B H 0.7520 0.1338 0.6797 0.070 Uiso 1 1 calc R . . . .
C10 C 0.5959(13) 0.323(2) 0.5992(7) 0.059(3) Uani 1 1 d D U . . .
H10A H 0.4708 0.3932 0.6137 0.070 Uiso 1 1 calc R . . . .
H10B H 0.7223 0.3848 0.5774 0.070 Uiso 1 1 calc R . . . .


_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
S1 O2 1.421(5) . ?
S1 C4 1.751(19) . ?
S1 N1 1.639(10) . ?
S1 O1 1.400(18) . ?
O3 C8 1.27(2) . ?
C8 N2 1.373(13) . ?
C8 N1 1.34(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.417(19) . ?
C4 C3 1.384(10) . ?
C4 C5 1.37(2) . ?
N1 H1 0.8600 . ?
N3 C14 1.488(13) . ?
N3 C9 1.471(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.33(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.40(2) . ?
C6 C1 1.392(10) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.59(3) . ?
C1 C2 1.41(2) . ?
C1 C7 1.48(2) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.473(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.515(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.509(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.496(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 108.9(7) . . ?
O2 S1 N1 108.2(4) . . ?
N1 S1 C4 105.0(9) . . ?
O1 S1 O2 121.3(10) . . ?
O1 S1 C4 108.4(8) . . ?
O1 S1 N1 103.9(7) . . ?
O3 C8 N2 118(2) . . ?
O3 C8 N1 123.8(10) . . ?
N1 C8 N2 118.3(16) . . ?
C8 N2 H2 121.9 . . ?
C8 N2 N3 116.2(17) . . ?
N3 N2 H2 121.9 . . ?
C3 C4 S1 119.4(13) . . ?
C5 C4 S1 119.5(8) . . ?
C5 C4 C3 121.0(14) . . ?
S1 N1 H1 118.5 . . ?
C8 N1 S1 123.0(12) . . ?
C8 N1 H1 118.5 . . ?
N2 N3 C14 111.5(9) . . ?
N2 N3 C9 109.0(14) . . ?
C9 N3 C14 115.2(7) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 C4 118.0(14) . . ?
C2 C3 H3 121.0 . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C1 C6 C5 120.6(13) . . ?
C4 C5 C6 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N3 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
N3 C14 C13 112.5(18) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C6 C1 C2 115.6(13) . . ?
C6 C1 C7 120.4(14) . . ?
C2 C1 C7 123.9(8) . . ?
C3 C2 C1 125.0(9) . . ?
C3 C2 H2A 117.5 . . ?
C1 C2 H2A 117.5 . . ?
N3 C9 H9A 107.5 . . ?
N3 C9 H9B 107.5 . . ?
N3 C9 C10 119.4(9) . . ?
H9A C9 H9B 107.0 . . ?
C10 C9 H9A 107.5 . . ?
C10 C9 H9B 107.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 C14 113.1(12) . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C13 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C12 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
H11A C11 H11B 107.2 . . ?
C10 C11 C12 117.3(6) . . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 108.0 . . ?
C9 C10 C11 114.5(15) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?

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
N2 H2 O3 0.86 1.97 2.82(3) 167.4 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 175.5(15) . . . . ?
S1 C4 C5 C6 -176.3(14) . . . . ?
O3 C8 N2 N3 -175.7(10) . . . . ?
O3 C8 N1 S1 1(2) . . . . ?
O2 S1 C4 C3 -173.2(13) . . . . ?
O2 S1 C4 C5 2.3(18) . . . . ?
O2 S1 N1 C8 -60.2(17) . . . . ?
C8 N2 N3 C14 -120.3(14) . . . . ?
C8 N2 N3 C9 111.4(12) . . . . ?
N2 C8 N1 S1 -177.3(6) . . . . ?
N2 N3 C14 C13 -60.7(13) . . . . ?
N2 N3 C9 C10 69.0(12) . . . . ?
C4 S1 N1 C8 55.9(13) . . . . ?
C4 C3 C2 C1 0(3) . . . . ?
N1 S1 C4 C3 71.2(16) . . . . ?
N1 S1 C4 C5 -113.3(14) . . . . ?
N1 C8 N2 N3 3.0(18) . . . . ?
O1 S1 C4 C3 -39.3(15) . . . . ?
O1 S1 C4 C5 136.1(15) . . . . ?
O1 S1 N1 C8 169.6(12) . . . . ?
N3 C14 C13 C12 -86.7(14) . . . . ?
N3 C9 C10 C11 77.5(14) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C6 C1 C2 C3 0(3) . . . . ?
C5 C4 C3 C2 0(3) . . . . ?
C5 C6 C1 C2 0(3) . . . . ?
C5 C6 C1 C7 -177.8(16) . . . . ?
C14 N3 C9 C10 -57(2) . . . . ?
C14 C13 C12 C11 57(2) . . . . ?
C1 C6 C5 C4 1(3) . . . . ?
C9 N3 C14 C13 64.3(16) . . . . ?
C7 C1 C2 C3 176.9(18) . . . . ?
C13 C12 C11 C10 15(3) . . . . ?
C12 C11 C10 C9 -74.5(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1p73GPA
_database_code_depnum_ccdc_archive 'CCDC 1493071'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1p73GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.354 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.0717(3)
_cell_length_b                   8.5574(5)
_cell_length_c                   13.251(2)
_cell_angle_alpha                81.402(9)
_cell_angle_beta                 86.675(9)
_cell_angle_gamma                82.667(5)
_cell_volume                     674.67(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    906
_cell_measurement_theta_min      2.4180
_cell_measurement_theta_max      26.2880

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1730000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3415
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         26.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.341
_diffrn_measured_fraction_theta_full 0.354
_diffrn_reflns_Laue_measured_fraction_max 0.341
_diffrn_reflns_Laue_measured_fraction_full 0.354
_diffrn_reflns_point_group_measured_fraction_max 0.341
_diffrn_reflns_point_group_measured_fraction_full 0.354
_reflns_number_total             939
_reflns_number_gt                666
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.6263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         939
_refine_ls_number_parameters     210
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.813
_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
S1 S 0.23979(18) 0.98623(15) 0.3912(3) 0.023(2) Uani 1 1 d . U . . .
O3 O 0.0517(6) 0.6763(4) 0.4143(8) 0.028(4) Uani 1 1 d . U . . .
N1 N 0.2579(6) 0.8377(4) 0.4828(9) 0.028(4) Uani 1 1 d . U . . .
H1 H 0.3372 0.8444 0.5333 0.034 Uiso 1 1 calc R U . . .
N3 N 0.3058(7) 0.6339(5) 0.6504(9) 0.023(4) Uani 1 1 d . U . . .
C4 C 0.4146(9) 0.9239(7) 0.2917(14) 0.026(3) Uani 1 1 d . U . . .
O2 O 0.0195(5) 1.0195(4) 0.3568(7) 0.026(5) Uani 1 1 d . U . . .
O1 O 0.3339(5) 1.1091(4) 0.4306(7) 0.029(5) Uani 1 1 d . U . . .
C8 C 0.1560(8) 0.7002(7) 0.4867(13) 0.022(4) Uani 1 1 d . U . . .
N2 N 0.1941(8) 0.5969(6) 0.5700(11) 0.028(4) Uani 1 1 d . U . . .
H2 H 0.1490 0.5047 0.5747 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6339(7) 0.8624(6) 0.3140(11) 0.026(5) Uani 1 1 d . U . . .
H3 H 0.6839 0.8499 0.3801 0.032 Uiso 1 1 calc R U . . .
C1 C 0.7018(10) 0.8371(8) 0.1303(15) 0.027(5) Uani 1 1 d . U . . .
C5 C 0.3392(10) 0.9362(7) 0.1953(15) 0.025(4) Uani 1 1 d . U . . .
H5 H 0.1911 0.9739 0.1833 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4801(8) 0.8933(6) 0.1148(12) 0.031(4) Uani 1 1 d . U . . .
H6 H 0.4250 0.9025 0.0498 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7734(10) 0.8209(8) 0.2333(15) 0.027(5) Uani 1 1 d . U . . .
H2A H 0.9203 0.7807 0.2463 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1567(8) 0.6275(7) 0.7459(12) 0.024(4) Uani 1 1 d . U . . .
H14A H 0.0043 0.6610 0.7268 0.029 Uiso 1 1 calc R U . . .
H14B H 0.1653 0.5182 0.7796 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8563(9) 0.7905(7) 0.0467(12) 0.036(6) Uani 1 1 d . U . . .
H7A H 0.9243 0.8814 0.0143 0.054 Uiso 1 1 calc R U . . .
H7B H 0.7759 0.7512 -0.0025 0.054 Uiso 1 1 calc R U . . .
H7C H 0.9693 0.7087 0.0740 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2166(8) 0.7301(7) 0.8193(11) 0.030(5) Uani 1 1 d . U . . .
H13A H 0.0862 0.7564 0.8622 0.036 Uiso 1 1 calc R U . . .
H13B H 0.2566 0.8287 0.7808 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4049(8) 0.6572(7) 0.8873(12) 0.038(5) Uani 1 1 d D U . . .
H12A H 0.4703 0.7472 0.9042 0.046 Uiso 0.069(18) 1 calc R U P A 1
H12B H 0.3331 0.6113 0.9501 0.046 Uiso 0.069(18) 1 calc R U P A 1
H12C H 0.4258 0.7298 0.9346 0.046 Uiso 0.931(18) 1 calc R U P A 2
H12D H 0.3650 0.5595 0.9270 0.046 Uiso 0.931(18) 1 calc R U P A 2
C11A C 0.600(14) 0.536(10) 0.868(7) 0.039(11) Uani 0.069(18) 1 d D U P A 1
H11A H 0.7314 0.5541 0.9010 0.047 Uiso 0.069(18) 1 calc R U P A 1
H11B H 0.5669 0.4284 0.8911 0.047 Uiso 0.069(18) 1 calc R U P A 1
C10A C 0.629(16) 0.568(16) 0.753(6) 0.033(9) Uani 0.069(18) 1 d D U P A 1
H10A H 0.6259 0.6827 0.7403 0.039 Uiso 0.069(18) 1 calc R U P A 1
H10B H 0.7840 0.5270 0.7419 0.039 Uiso 0.069(18) 1 calc R U P A 1
C11B C 0.6218(9) 0.6209(12) 0.8281(13) 0.037(6) Uani 0.931(18) 1 d D U P A 2
H11C H 0.6547 0.7163 0.7833 0.045 Uiso 0.931(18) 1 calc R U P A 2
H11D H 0.7408 0.5909 0.8756 0.045 Uiso 0.931(18) 1 calc R U P A 2
C10B C 0.6144(11) 0.4889(10) 0.7654(11) 0.033(5) Uani 0.931(18) 1 d D U P A 2
H10C H 0.7643 0.4357 0.7584 0.040 Uiso 0.931(18) 1 calc R U P A 2
H10D H 0.5257 0.4119 0.8037 0.040 Uiso 0.931(18) 1 calc R U P A 2
C9 C 0.5238(9) 0.5333(7) 0.6598(12) 0.032(5) Uani 1 1 d D U . . .
H9A H 0.6182 0.5581 0.5994 0.039 Uiso 0.069(18) 1 calc R U P A 1
H9B H 0.5031 0.4216 0.6670 0.039 Uiso 0.069(18) 1 calc R U P A 1
H9C H 0.6323 0.5885 0.6165 0.039 Uiso 0.931(18) 1 calc R U P A 2
H9D H 0.5113 0.4356 0.6328 0.039 Uiso 0.931(18) 1 calc R U P A 2


_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
S1 O2 1.419(4) . ?
S1 O1 1.434(4) . ?
S1 N1 1.619(9) . ?
S1 C4 1.746(14) . ?
O3 C8 1.235(15) . ?
N1 C8 1.390(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.391(15) . ?
N3 C9 1.485(7) . ?
N3 C14 1.511(17) . ?
C4 C5 1.37(3) . ?
C4 C3 1.399(9) . ?
C8 N2 1.319(19) . ?
N2 H2 0.8600 . ?
C3 C2 1.386(18) . ?
C3 H3 0.9300 . ?
C1 C6 1.387(9) . ?
C1 C7 1.477(18) . ?
C1 C2 1.44(3) . ?
C5 C6 1.392(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.492(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.509(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11A 1.508(19) . ?
C12 C11B 1.515(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C11A C10A 1.509(19) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C10A C9 1.510(19) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11B C10B 1.506(12) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C10B C9 1.510(14) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 H9D 0.9700 . ?

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 S1 O1 118.4(2) . . ?
O2 S1 N1 110.4(3) . . ?
O1 S1 N1 104.5(5) . . ?
O2 S1 C4 108.5(5) . . ?
O1 S1 C4 108.6(3) . . ?
N1 S1 C4 105.7(5) . . ?
C8 N1 S1 125.5(9) . . ?
C8 N1 H1 117.2 . . ?
S1 N1 H1 117.2 . . ?
N2 N3 C9 109.6(7) . . ?
N2 N3 C14 110.0(6) . . ?
C9 N3 C14 115.8(10) . . ?
C5 C4 C3 121.3(13) . . ?
C5 C4 S1 120.8(5) . . ?
C3 C4 S1 117.8(12) . . ?
O3 C8 N2 124.4(6) . . ?
O3 C8 N1 121.3(12) . . ?
N2 C8 N1 114.1(11) . . ?
C8 N2 N3 121.4(6) . . ?
C8 N2 H2 119.3 . . ?
N3 N2 H2 119.3 . . ?
C2 C3 C4 117.1(13) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C6 C1 C7 122.2(14) . . ?
C6 C1 C2 116.6(14) . . ?
C7 C1 C2 121.2(7) . . ?
C4 C5 C6 121.2(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 120.7(14) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C3 C2 C1 123.1(7) . . ?
C3 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
C13 C14 N3 113.1(6) . . ?
C13 C14 H14A 109.0 . . ?
N3 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
N3 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 115.1(5) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C11A C12 C13 130(5) . . ?
C11B C12 C13 112.9(11) . . ?
C11A C12 H12A 104.9 . . ?
C13 C12 H12A 104.9 . . ?
C11A C12 H12B 104.9 . . ?
C13 C12 H12B 104.9 . . ?
H12A C12 H12B 105.8 . . ?
C11B C12 H12C 109.0 . . ?
C13 C12 H12C 109.0 . . ?
C11B C12 H12D 109.0 . . ?
C13 C12 H12D 109.0 . . ?
H12C C12 H12D 107.8 . . ?
C10A C11A C12 102(6) . . ?
C10A C11A H11A 111.5 . . ?
C12 C11A H11A 111.5 . . ?
C10A C11A H11B 111.5 . . ?
C12 C11A H11B 111.5 . . ?
H11A C11A H11B 109.3 . . ?
C9 C10A C11A 139(10) . . ?
C9 C10A H10A 102.3 . . ?
C11A C10A H10A 102.3 . . ?
C9 C10A H10B 102.3 . . ?
C11A C10A H10B 102.3 . . ?
H10A C10A H10B 104.9 . . ?
C10B C11B C12 112.3(6) . . ?
C10B C11B H11C 109.1 . . ?
C12 C11B H11C 109.1 . . ?
C10B C11B H11D 109.1 . . ?
C12 C11B H11D 109.1 . . ?
H11C C11B H11D 107.9 . . ?
C9 C10B C11B 117.6(10) . . ?
C9 C10B H10C 107.9 . . ?
C11B C10B H10C 107.9 . . ?
C9 C10B H10D 107.9 . . ?
C11B C10B H10D 107.9 . . ?
H10C C10B H10D 107.2 . . ?
N3 C9 C10B 117.3(10) . . ?
N3 C9 C10A 108(4) . . ?
N3 C9 H9A 110.2 . . ?
C10A C9 H9A 110.2 . . ?
N3 C9 H9B 110.2 . . ?
C10A C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N3 C9 H9C 108.0 . . ?
C10B C9 H9C 108.0 . . ?
N3 C9 H9D 108.0 . . ?
C10B C9 H9D 108.0 . . ?
H9C C9 H9D 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 40.7(8) . . . . ?
O1 S1 N1 C8 169.0(6) . . . . ?
C4 S1 N1 C8 -76.5(7) . . . . ?
O2 S1 C4 C5 9.8(8) . . . . ?
O1 S1 C4 C5 -120.1(7) . . . . ?
N1 S1 C4 C5 128.2(7) . . . . ?
O2 S1 C4 C3 -170.7(5) . . . . ?
O1 S1 C4 C3 59.4(7) . . . . ?
N1 S1 C4 C3 -52.3(6) . . . . ?
S1 N1 C8 O3 4.9(11) . . . . ?
S1 N1 C8 N2 -179.3(6) . . . . ?
O3 C8 N2 N3 -177.5(7) . . . . ?
N1 C8 N2 N3 6.9(12) . . . . ?
C9 N3 N2 C8 -113.1(9) . . . . ?
C14 N3 N2 C8 118.6(9) . . . . ?
C5 C4 C3 C2 2.6(11) . . . . ?
S1 C4 C3 C2 -176.9(5) . . . . ?
C3 C4 C5 C6 -2.3(12) . . . . ?
S1 C4 C5 C6 177.1(4) . . . . ?
C7 C1 C6 C5 -180.0(6) . . . . ?
C2 C1 C6 C5 2.1(10) . . . . ?
C4 C5 C6 C1 -0.1(11) . . . . ?
C4 C3 C2 C1 -0.6(11) . . . . ?
C6 C1 C2 C3 -1.7(12) . . . . ?
C7 C1 C2 C3 -179.7(5) . . . . ?
N2 N3 C14 C13 -154.5(6) . . . . ?
C9 N3 C14 C13 80.6(7) . . . . ?
N3 C14 C13 C12 -82.0(11) . . . . ?
C14 C13 C12 C11A 29(6) . . . . ?
C14 C13 C12 C11B 61.9(10) . . . . ?
C13 C12 C11A C10A 28(12) . . . . ?
C12 C11A C10A C9 -78(17) . . . . ?
C13 C12 C11B C10B -68.0(12) . . . . ?
C12 C11B C10B C9 86.2(13) . . . . ?
N2 N3 C9 C10B -148.8(8) . . . . ?
C14 N3 C9 C10B -23.6(7) . . . . ?
N2 N3 C9 C10A -175(5) . . . . ?
C14 N3 C9 C10A -50(5) . . . . ?
C11B C10B C9 N3 -50.4(10) . . . . ?
C11A C10A C9 N3 72(14) . . . . ?

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
N1 H1 O1 0.86 2.18 2.906(7) 142.1 2_676
N2 H2 O3 0.86 2.07 2.907(5) 162.8 2_566

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_272GPa
_database_code_depnum_ccdc_archive 'CCDC 1495206'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9122(3)
_cell_length_b                   8.617(4)
_cell_length_c                   12.9150(17)
_cell_angle_alpha                80.610(19)
_cell_angle_beta                 85.576(7)
_cell_angle_gamma                85.688(12)
_cell_volume                     645.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    799
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       2720000
_cell_measurement_theta_min      3.1000
_cell_measurement_theta_max      26.4410
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.395
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_Laue_measured_fraction_full 0.342
_diffrn_reflns_Laue_measured_fraction_max 0.334
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3208
_diffrn_reflns_point_group_measured_fraction_full 0.342
_diffrn_reflns_point_group_measured_fraction_max 0.334
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         1.602
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         2720000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.342
_diffrn_measured_fraction_theta_max 0.334
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                493
_reflns_number_total             885
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         885
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1030P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.2127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0218(4) 0.2545(7) 0.2189(2) 0.042(2) Uani 1 1 d . U . . .
O3 O -0.0675(8) 0.4493(17) 0.3800(5) 0.047(5) Uani 1 1 d . U . . .
O2 O -0.2190(8) 0.2516(15) 0.2331(5) 0.033(7) Uani 1 1 d . U . . .
C8 C 0.0650(13) 0.333(3) 0.4009(8) 0.042(2) Uani 1 1 d . U . . .
N2 N 0.1590(9) 0.305(2) 0.4964(6) 0.043(2) Uani 1 1 d . U . . .
H2 H 0.1184 0.3620 0.5444 0.051 Uiso 1 1 calc R . . . .
C4 C 0.0928(12) 0.440(2) 0.1571(7) 0.043(3) Uani 1 1 d . U . . .
N1 N 0.1278(10) 0.233(2) 0.3350(6) 0.042(2) Uani 1 1 d . U . . .
H1 H 0.2254 0.1562 0.3529 0.051 Uiso 1 1 calc R . . . .
O1 O 0.1527(9) 0.1353(18) 0.1680(5) 0.050(4) Uani 1 1 d . U . . .
N3 N 0.3259(10) 0.1785(19) 0.5126(6) 0.043(2) Uani 1 1 d . U . . .
C3 C 0.3198(12) 0.469(2) 0.1271(7) 0.043(3) Uani 1 1 d . U . . .
H3 H 0.4361 0.3927 0.1447 0.052 Uiso 1 1 calc R . . . .
C6 C -0.0222(12) 0.697(2) 0.0743(7) 0.043(3) Uani 1 1 d . U . . .
H6 H -0.1378 0.7730 0.0544 0.052 Uiso 1 1 calc R . . . .
C5 C -0.0788(12) 0.554(2) 0.1322(7) 0.043(3) Uani 1 1 d . U . . .
H5 H -0.2294 0.5356 0.1538 0.052 Uiso 1 1 calc R . . . .
C14 C 0.2627(13) 0.069(2) 0.6093(7) 0.043(2) Uani 1 1 d . U . . .
H14A H 0.3768 -0.0184 0.6177 0.052 Uiso 1 1 calc R . . . .
H14B H 0.1192 0.0264 0.6008 0.052 Uiso 1 1 calc R . . . .
C1 C 0.2022(12) 0.731(2) 0.0449(7) 0.043(3) Uani 1 1 d . U . . .
C2 C 0.3657(12) 0.613(3) 0.0714(7) 0.043(3) Uani 1 1 d . U . . .
H2A H 0.5163 0.6314 0.0500 0.052 Uiso 1 1 calc R . . . .
C9 C 0.5533(12) 0.244(2) 0.5116(7) 0.043(2) Uani 1 1 d D U . . .
H9A H 0.6675 0.1567 0.5116 0.052 Uiso 1 1 calc R . . . .
H9B H 0.5772 0.3141 0.4456 0.052 Uiso 1 1 calc R . . . .
C7 C 0.2659(13) 0.889(2) -0.0130(8) 0.054(8) Uani 1 1 d . U . . .
H7A H 0.1620 0.9246 -0.0667 0.081 Uiso 1 1 calc GR . . . .
H7B H 0.4176 0.8791 -0.0447 0.081 Uiso 1 1 calc GR . . . .
H7C H 0.2589 0.9627 0.0353 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.2395(12) 0.145(2) 0.7118(7) 0.044(2) Uani 1 1 d . U . . .
H13A H 0.1849 0.2548 0.6949 0.052 Uiso 1 1 calc R . . . .
H13B H 0.1285 0.0915 0.7615 0.052 Uiso 1 1 calc R . . . .
C12 C 0.4638(11) 0.136(2) 0.7618(7) 0.044(3) Uani 1 1 d D U . . .
H12A H 0.5139 0.0254 0.7792 0.052 Uiso 1 1 calc R . . . .
H12B H 0.4375 0.1774 0.8274 0.052 Uiso 1 1 calc R . . . .
C11 C 0.6560(12) 0.221(2) 0.6979(7) 0.044(3) Uani 1 1 d D U . . .
H11A H 0.7710 0.1420 0.6790 0.052 Uiso 1 1 calc R . . . .
H11B H 0.7243 0.2815 0.7428 0.052 Uiso 1 1 calc R . . . .
C10 C 0.5969(12) 0.330(2) 0.5982(7) 0.043(2) Uani 1 1 d D U . . .
H10A H 0.4628 0.3971 0.6133 0.052 Uiso 1 1 calc R . . . .
H10B H 0.7211 0.3981 0.5752 0.052 Uiso 1 1 calc R . . . .


_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
S1 O2 1.423(5) . ?
S1 C4 1.731(17) . ?
S1 N1 1.647(8) . ?
S1 O1 1.452(16) . ?
O3 C8 1.23(2) . ?
C8 N2 1.370(11) . ?
C8 N1 1.32(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.415(18) . ?
C4 C3 1.398(10) . ?
C4 C5 1.379(19) . ?
N1 H1 0.8600 . ?
N3 C14 1.479(11) . ?
N3 C9 1.493(13) . ?
C3 H3 0.9300 . ?
C3 C2 1.36(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.38(2) . ?
C6 C1 1.391(10) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.56(2) . ?
C1 C2 1.37(2) . ?
C1 C7 1.50(2) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.491(17) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.510(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.514(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.515(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 109.2(6) . . ?
O2 S1 N1 108.9(4) . . ?
O2 S1 O1 120.0(8) . . ?
N1 S1 C4 104.9(8) . . ?
O1 S1 C4 109.5(7) . . ?
O1 S1 N1 103.2(7) . . ?
O3 C8 N2 119.3(19) . . ?
O3 C8 N1 123.6(10) . . ?
N1 C8 N2 117.1(15) . . ?
C8 N2 H2 121.5 . . ?
C8 N2 N3 116.9(15) . . ?
N3 N2 H2 121.5 . . ?
C3 C4 S1 120.2(12) . . ?
C5 C4 S1 118.9(7) . . ?
C5 C4 C3 120.8(13) . . ?
S1 N1 H1 119.6 . . ?
C8 N1 S1 120.9(10) . . ?
C8 N1 H1 119.6 . . ?
N2 N3 C14 110.0(8) . . ?
N2 N3 C9 108.9(13) . . ?
C14 N3 C9 114.4(6) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 C4 118.0(13) . . ?
C2 C3 H3 121.0 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C1 122.1(12) . . ?
C1 C6 H6 119.0 . . ?
C4 C5 C6 118.6(8) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
N3 C14 H14A 108.7 . . ?
N3 C14 H14B 108.7 . . ?
N3 C14 C13 114.3(16) . . ?
H14A C14 H14B 107.6 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C6 C1 C7 122.5(13) . . ?
C2 C1 C6 116.7(14) . . ?
C2 C1 C7 120.8(8) . . ?
C3 C2 C1 123.7(8) . . ?
C3 C2 H2A 118.1 . . ?
C1 C2 H2A 118.1 . . ?
N3 C9 H9A 107.7 . . ?
N3 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 N3 118.3(9) . . ?
C10 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 C14 111.5(11) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C13 C12 C11 117.1(6) . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
C12 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
C12 C11 C10 117.2(6) . . ?
H11A C11 H11B 107.2 . . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 108.0 . . ?
C9 C10 C11 112.5(13) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?

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
N2 H2 O3 0.86 2.02 2.85(2) 161.0 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 174.8(13) . . . . ?
S1 C4 C5 C6 -174.1(12) . . . . ?
O3 C8 N2 N3 -174.2(9) . . . . ?
O3 C8 N1 S1 -2.7(18) . . . . ?
O2 S1 C4 C3 -175.1(12) . . . . ?
O2 S1 C4 C5 0.7(16) . . . . ?
O2 S1 N1 C8 -58.0(14) . . . . ?
C8 N2 N3 C14 -125.7(12) . . . . ?
C8 N2 N3 C9 108.1(12) . . . . ?
N2 C8 N1 S1 179.1(7) . . . . ?
N2 N3 C14 C13 -60.1(12) . . . . ?
N2 N3 C9 C10 66.5(11) . . . . ?
C4 S1 N1 C8 58.9(11) . . . . ?
C4 C3 C2 C1 1(3) . . . . ?
N1 S1 C4 C3 68.3(15) . . . . ?
N1 S1 C4 C5 -115.9(13) . . . . ?
N1 C8 N2 N3 4.1(16) . . . . ?
O1 S1 C4 C3 -41.8(14) . . . . ?
O1 S1 C4 C5 134.0(13) . . . . ?
O1 S1 N1 C8 173.5(10) . . . . ?
N3 C14 C13 C12 -88.5(12) . . . . ?
N3 C9 C10 C11 80.1(12) . . . . ?
C3 C4 C5 C6 2(3) . . . . ?
C6 C1 C2 C3 -3(3) . . . . ?
C5 C4 C3 C2 -1(2) . . . . ?
C5 C6 C1 C2 3(3) . . . . ?
C5 C6 C1 C7 -176.8(15) . . . . ?
C14 N3 C9 C10 -57.1(19) . . . . ?
C14 C13 C12 C11 62(2) . . . . ?
C1 C6 C5 C4 -3(3) . . . . ?
C9 N3 C14 C13 62.9(15) . . . . ?
C7 C1 C2 C3 177.6(15) . . . . ?
C13 C12 C11 C10 10(2) . . . . ?
C12 C11 C10 C9 -74.2(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_501GPa
_database_code_depnum_ccdc_archive 'CCDC 1495209'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            tolazamide
_chemical_name_systematic        
;
'N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide'
;
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7692(2)
_cell_length_b                   8.421(2)
_cell_length_c                   12.7212(11)
_cell_angle_alpha                81.231(12)
_cell_angle_beta                 84.740(5)
_cell_angle_gamma                85.557(9)
_cell_volume                     606.96(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    776
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       5010000
_cell_measurement_theta_min      1.6450
_cell_measurement_theta_max      26.2530
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.1066
_diffrn_reflns_Laue_measured_fraction_full 0.341
_diffrn_reflns_Laue_measured_fraction_max 0.335
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3086
_diffrn_reflns_point_group_measured_fraction_full 0.341
_diffrn_reflns_point_group_measured_fraction_max 0.335
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_min         1.625
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         5010000
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.341
_diffrn_measured_fraction_theta_max 0.335
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                554
_reflns_number_total             834
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         834
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0160P)²+0.4438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 \\sim C11-C10 \\sim C10-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.001 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), C6(H6), C5(H5), C2(H2A)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.0195(3) 0.2495(6) 0.21717(14) 0.0304(17) Uani 1 1 d . U . . .
O3 O -0.0675(6) 0.4511(13) 0.3781(3) 0.034(4) Uani 1 1 d . U . . .
O2 O -0.2282(6) 0.2477(12) 0.2341(3) 0.025(6) Uani 1 1 d . U . . .
C8 C 0.0645(10) 0.338(2) 0.4028(5) 0.0305(18) Uani 1 1 d . U . . .
N2 N 0.1553(7) 0.3038(15) 0.4979(4) 0.0308(18) Uani 1 1 d . U . . .
H2 H 0.1087 0.3593 0.5481 0.037 Uiso 1 1 calc R . . . .
C4 C 0.0900(9) 0.4405(19) 0.1558(5) 0.028(3) Uani 1 1 d . U . . .
N1 N 0.1316(8) 0.2282(16) 0.3333(4) 0.0307(18) Uani 1 1 d . U . . .
H1 H 0.2312 0.1493 0.3506 0.037 Uiso 1 1 calc R . . . .
O1 O 0.1508(7) 0.1304(14) 0.1628(4) 0.035(3) Uani 1 1 d . U . . .
N3 N 0.3276(7) 0.1764(15) 0.5144(4) 0.0313(18) Uani 1 1 d . U . . .
C3 C 0.3208(9) 0.4674(19) 0.1268(5) 0.028(3) Uani 1 1 d . U . . .
H3 H 0.4388 0.3892 0.1453 0.034 Uiso 1 1 calc R . . . .
C6 C -0.0307(9) 0.6992(19) 0.0726(5) 0.028(3) Uani 1 1 d . U . . .
H6 H -0.1504 0.7751 0.0526 0.034 Uiso 1 1 calc R . . . .
C5 C -0.0857(9) 0.5562(19) 0.1316(5) 0.028(3) Uani 1 1 d . U . . .
H5 H -0.2399 0.5372 0.1550 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2618(10) 0.0679(19) 0.6134(5) 0.0314(18) Uani 1 1 d . U . . .
H14A H 0.3766 -0.0227 0.6209 0.038 Uiso 1 1 calc R . . . .
H14B H 0.1130 0.0260 0.6063 0.038 Uiso 1 1 calc R . . . .
C1 C 0.1993(9) 0.7355(19) 0.0412(5) 0.028(3) Uani 1 1 d . U . . .
C2 C 0.3699(9) 0.6138(19) 0.0696(5) 0.028(3) Uani 1 1 d . U . . .
H2A H 0.5250 0.6332 0.0486 0.034 Uiso 1 1 calc R . . . .
C9 C 0.5559(9) 0.2426(17) 0.5107(5) 0.0320(18) Uani 1 1 d D U . . .
H9A H 0.5804 0.3120 0.4429 0.038 Uiso 1 1 calc R . . . .
H9B H 0.6738 0.1540 0.5112 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2695(9) 0.8909(19) -0.0173(5) 0.031(6) Uani 1 1 d . U . . .
H7A H 0.1584 0.9319 -0.0681 0.046 Uiso 1 1 calc GR . . . .
H7B H 0.4208 0.8764 -0.0541 0.046 Uiso 1 1 calc GR . . . .
H7C H 0.2752 0.9659 0.0320 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.2425(9) 0.1447(19) 0.7145(5) 0.0314(19) Uani 1 1 d . U . . .
H13A H 0.1806 0.2553 0.6981 0.038 Uiso 1 1 calc R . . . .
H13B H 0.1318 0.0884 0.7662 0.038 Uiso 1 1 calc R . . . .
C12 C 0.4704(8) 0.1437(18) 0.7645(5) 0.0320(19) Uani 1 1 d D U . . .
H12A H 0.4389 0.1897 0.8302 0.038 Uiso 1 1 calc R . . . .
H12B H 0.5272 0.0325 0.7836 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6637(9) 0.2324(17) 0.6977(5) 0.0322(19) Uani 1 1 d D U . . .
H11A H 0.7289 0.2995 0.7416 0.039 Uiso 1 1 calc R . . . .
H11B H 0.7861 0.1536 0.6790 0.039 Uiso 1 1 calc R . . . .
C10 C 0.5982(10) 0.3363(17) 0.5971(4) 0.0321(19) Uani 1 1 d D U . . .
H10A H 0.4582 0.4027 0.6130 0.039 Uiso 1 1 calc R . . . .
H10B H 0.7222 0.4075 0.5715 0.039 Uiso 1 1 calc R . . . .


_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
S1 O2 1.427(4) . ?
S1 C4 1.738(14) . ?
S1 N1 1.645(5) . ?
S1 O1 1.434(12) . ?
O3 C8 1.196(14) . ?
C8 N2 1.344(7) . ?
C8 N1 1.38(2) . ?
N2 H2 0.8600 . ?
N2 N3 1.410(13) . ?
C4 C3 1.376(7) . ?
C4 C5 1.373(15) . ?
N1 H1 0.8600 . ?
N3 C14 1.477(9) . ?
N3 C9 1.464(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.368(17) . ?
C6 H6 0.9300 . ?
C6 C5 1.362(17) . ?
C6 C1 1.393(8) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.517(17) . ?
C1 C2 1.395(15) . ?
C1 C7 1.470(17) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.495(15) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.511(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.511(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.497(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 S1 C4 108.5(5) . . ?
O2 S1 N1 109.2(3) . . ?
O2 S1 O1 120.3(6) . . ?
N1 S1 C4 104.4(5) . . ?
O1 S1 C4 109.5(5) . . ?
O1 S1 N1 103.7(5) . . ?
O3 C8 N2 124.3(13) . . ?
O3 C8 N1 120.9(7) . . ?
N2 C8 N1 114.9(11) . . ?
C8 N2 H2 120.3 . . ?
C8 N2 N3 119.3(11) . . ?
N3 N2 H2 120.3 . . ?
C3 C4 S1 118.5(9) . . ?
C5 C4 S1 119.3(5) . . ?
C5 C4 C3 122.0(11) . . ?
S1 N1 H1 120.2 . . ?
C8 N1 S1 119.6(7) . . ?
C8 N1 H1 120.2 . . ?
N2 N3 C14 109.7(6) . . ?
N2 N3 C9 109.3(10) . . ?
C9 N3 C14 114.9(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 C4 117.3(10) . . ?
C2 C3 H3 121.3 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C1 122.1(9) . . ?
C1 C6 H6 118.9 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(6) . . ?
C6 C5 H5 120.5 . . ?
N3 C14 H14A 108.5 . . ?
N3 C14 H14B 108.5 . . ?
N3 C14 C13 115.0(12) . . ?
H14A C14 H14B 107.5 . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C6 C1 C2 116.1(10) . . ?
C6 C1 C7 124.5(9) . . ?
C2 C1 C7 119.5(6) . . ?
C3 C2 C1 123.4(6) . . ?
C3 C2 H2A 118.3 . . ?
C1 C2 H2A 118.3 . . ?
N3 C9 H9A 107.9 . . ?
N3 C9 H9B 107.9 . . ?
N3 C9 C10 117.8(7) . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C12 C13 C14 114.2(8) . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 C13 116.8(5) . . ?
C11 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C10 C11 C12 116.6(4) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C9 C10 C11 113.4(11) . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?

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
N2 H2 O3 0.86 1.96 2.773(18) 157.1 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 173.9(9) . . . . ?
S1 C4 C5 C6 -172.5(9) . . . . ?
O3 C8 N2 N3 -173.6(8) . . . . ?
O3 C8 N1 S1 -2.7(12) . . . . ?
O2 S1 C4 C3 -176.7(8) . . . . ?
O2 S1 C4 C5 -0.9(10) . . . . ?
O2 S1 N1 C8 -58.2(10) . . . . ?
C8 N2 N3 C14 -129.0(9) . . . . ?
C8 N2 N3 C9 104.2(9) . . . . ?
N2 C8 N1 S1 176.1(5) . . . . ?
N2 N3 C14 C13 -62.1(8) . . . . ?
N2 N3 C9 C10 66.3(8) . . . . ?
C4 S1 N1 C8 57.7(8) . . . . ?
C4 C3 C2 C1 0.9(17) . . . . ?
N1 S1 C4 C3 66.9(10) . . . . ?
N1 S1 C4 C5 -117.3(8) . . . . ?
N1 C8 N2 N3 7.7(11) . . . . ?
O1 S1 C4 C3 -43.6(9) . . . . ?
O1 S1 C4 C5 132.2(9) . . . . ?
O1 S1 N1 C8 172.4(7) . . . . ?
N3 C14 C13 C12 -85.9(10) . . . . ?
N3 C9 C10 C11 81.5(9) . . . . ?
C3 C4 C5 C6 3.2(17) . . . . ?
C6 C1 C2 C3 -1.3(16) . . . . ?
C5 C4 C3 C2 -1.8(17) . . . . ?
C5 C6 C1 C2 2.8(16) . . . . ?
C5 C6 C1 C7 -176.5(11) . . . . ?
C14 N3 C9 C10 -57.4(15) . . . . ?
C14 C13 C12 C11 61.0(16) . . . . ?
C1 C6 C5 C4 -3.7(18) . . . . ?
C9 N3 C14 C13 61.5(12) . . . . ?
C7 C1 C2 C3 178.0(11) . . . . ?
C13 C12 C11 C10 10.5(18) . . . . ?
C12 C11 C10 C9 -73.4(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2p50GPA
_database_code_depnum_ccdc_archive 'CCDC 1493072'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2p50GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.9953(3)
_cell_length_b                   8.4598(4)
_cell_length_c                   13.189(2)
_cell_angle_alpha                81.453(9)
_cell_angle_beta                 86.954(9)
_cell_angle_gamma                82.427(4)
_cell_volume                     655.38(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      2.4480
_cell_measurement_theta_max      26.2360

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         2500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3276
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.454
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.337
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.337
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.337
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             904
_reflns_number_gt                643
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.0519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         904
_refine_ls_number_parameters     210
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.856
_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
S1 S 0.23609(17) 0.98910(14) 0.3913(3) 0.023(2) Uani 1 1 d . U . . .
O3 O 0.0504(5) 0.6769(4) 0.4141(7) 0.026(4) Uani 1 1 d . U . . .
N1 N 0.2579(5) 0.8394(4) 0.4826(8) 0.022(4) Uani 1 1 d . U . . .
H1 H 0.3371 0.8461 0.5339 0.026 Uiso 1 1 calc R U . . .
N3 N 0.3078(6) 0.6334(5) 0.6512(9) 0.022(4) Uani 1 1 d . U . . .
C4 C 0.4128(9) 0.9261(7) 0.2902(14) 0.021(3) Uani 1 1 d . U . . .
O2 O 0.0129(4) 1.0225(4) 0.3567(6) 0.025(4) Uani 1 1 d . U . . .
O1 O 0.3315(5) 1.1140(4) 0.4311(7) 0.029(5) Uani 1 1 d . U . . .
C8 C 0.1575(8) 0.7000(7) 0.4842(13) 0.020(4) Uani 1 1 d . U . . .
N2 N 0.1954(7) 0.5948(6) 0.5721(11) 0.026(4) Uani 1 1 d . U . . .
H2 H 0.1479 0.5022 0.5781 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6351(7) 0.8640(6) 0.3131(11) 0.022(5) Uani 1 1 d . U . . .
H3 H 0.6874 0.8506 0.3793 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7021(10) 0.8364(8) 0.1312(15) 0.023(5) Uani 1 1 d . U . . .
C5 C 0.3346(9) 0.9400(7) 0.1971(15) 0.023(4) Uani 1 1 d . U . . .
H5 H 0.1842 0.9793 0.1861 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4768(7) 0.8958(6) 0.1134(12) 0.025(4) Uani 1 1 d . U . . .
H6 H 0.4208 0.9062 0.0480 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7740(10) 0.8230(8) 0.2296(15) 0.024(5) Uani 1 1 d . U . . .
H2A H 0.9243 0.7844 0.2416 0.029 Uiso 1 1 calc R U . . .
C14 C 0.1570(8) 0.6268(7) 0.7437(12) 0.026(4) Uani 1 1 d . U . . .
H14A H 0.1650 0.5162 0.7772 0.032 Uiso 1 1 calc R U . . .
H14B H 0.0032 0.6615 0.7232 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8590(9) 0.7891(7) 0.0449(13) 0.038(6) Uani 1 1 d . U . . .
H7A H 0.9389 0.8779 0.0172 0.056 Uiso 1 1 calc R U . . .
H7B H 0.7737 0.7610 -0.0079 0.056 Uiso 1 1 calc R U . . .
H7C H 0.9646 0.6983 0.0703 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2161(7) 0.7304(6) 0.8184(11) 0.031(5) Uani 1 1 d . U . . .
H13A H 0.0819 0.7600 0.8592 0.037 Uiso 1 1 calc R U . . .
H13B H 0.2609 0.8289 0.7800 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4064(8) 0.6532(7) 0.8922(12) 0.032(5) Uani 1 1 d D U . . .
H12A H 0.4726 0.7426 0.9113 0.039 Uiso 0.043(13) 1 calc R U P A 1
H12B H 0.3307 0.6053 0.9537 0.039 Uiso 0.043(13) 1 calc R U P A 1
H12C H 0.4253 0.7263 0.9403 0.039 Uiso 0.957(13) 1 calc R U P A 2
H12D H 0.3639 0.5544 0.9311 0.039 Uiso 0.957(13) 1 calc R U P A 2
C11A C 0.603(18) 0.529(12) 0.870(10) 0.027(11) Uani 0.043(13) 1 d D U P A 1
H11A H 0.7410 0.5436 0.9014 0.032 Uiso 0.043(13) 1 calc R U P A 1
H11B H 0.5704 0.4192 0.8879 0.032 Uiso 0.043(13) 1 calc R U P A 1
C10A C 0.60(2) 0.59(2) 0.756(8) 0.022(10) Uani 0.043(13) 1 d D U P A 1
H10A H 0.5147 0.6955 0.7531 0.027 Uiso 0.043(13) 1 calc R U P A 1
H10B H 0.7541 0.6083 0.7396 0.027 Uiso 0.043(13) 1 calc R U P A 1
C11B C 0.6265(9) 0.6163(10) 0.8343(13) 0.026(5) Uani 0.957(13) 1 d D U P A 2
H11C H 0.7452 0.5826 0.8830 0.032 Uiso 0.957(13) 1 calc R U P A 2
H11D H 0.6624 0.7137 0.7914 0.032 Uiso 0.957(13) 1 calc R U P A 2
C10B C 0.6206(9) 0.4846(7) 0.7671(10) 0.024(5) Uani 0.957(13) 1 d D U P A 2
H10C H 0.7728 0.4309 0.7606 0.029 Uiso 0.957(13) 1 calc R U P A 2
H10D H 0.5308 0.4057 0.8038 0.029 Uiso 0.957(13) 1 calc R U P A 2
C9 C 0.5309(9) 0.5317(7) 0.6599(12) 0.023(5) Uani 1 1 d D U . . .
H9A H 0.6316 0.5575 0.6015 0.028 Uiso 0.043(13) 1 calc R U P A 1
H9B H 0.5173 0.4174 0.6702 0.028 Uiso 0.043(13) 1 calc R U P A 1
H9C H 0.6403 0.5891 0.6177 0.028 Uiso 0.957(13) 1 calc R U P A 2
H9D H 0.5201 0.4338 0.6314 0.028 Uiso 0.957(13) 1 calc R U P A 2


_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
S1 O2 1.416(4) . ?
S1 O1 1.441(4) . ?
S1 N1 1.610(9) . ?
S1 C4 1.760(14) . ?
O3 C8 1.207(14) . ?
N1 C8 1.389(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.372(14) . ?
N3 C14 1.478(16) . ?
N3 C9 1.492(7) . ?
C4 C5 1.32(3) . ?
C4 C3 1.398(9) . ?
C8 N2 1.362(19) . ?
N2 H2 0.8600 . ?
C3 C2 1.403(19) . ?
C3 H3 0.9300 . ?
C1 C2 1.37(3) . ?
C1 C6 1.397(9) . ?
C1 C7 1.504(19) . ?
C5 C6 1.423(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.496(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.552(15) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11B 1.509(10) . ?
C12 C11A 1.516(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C11A C10A 1.52(2) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C10A C9 1.52(2) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11B C10B 1.528(12) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C10B C9 1.518(14) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 H9D 0.9700 . ?

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 S1 O1 118.47(18) . . ?
O2 S1 N1 110.7(3) . . ?
O1 S1 N1 104.4(4) . . ?
O2 S1 C4 108.2(5) . . ?
O1 S1 C4 108.7(3) . . ?
N1 S1 C4 105.7(5) . . ?
C8 N1 S1 124.5(9) . . ?
C8 N1 H1 117.7 . . ?
S1 N1 H1 117.7 . . ?
N2 N3 C14 108.6(5) . . ?
N2 N3 C9 109.1(7) . . ?
C14 N3 C9 117.1(10) . . ?
C5 C4 C3 122.7(14) . . ?
C5 C4 S1 120.1(6) . . ?
C3 C4 S1 117.2(12) . . ?
O3 C8 N2 124.7(6) . . ?
O3 C8 N1 122.6(12) . . ?
N2 C8 N1 112.7(10) . . ?
N3 N2 C8 121.4(6) . . ?
N3 N2 H2 119.3 . . ?
C8 N2 H2 119.3 . . ?
C2 C3 C4 115.6(13) . . ?
C2 C3 H3 122.2 . . ?
C4 C3 H3 122.2 . . ?
C2 C1 C6 117.7(14) . . ?
C2 C1 C7 121.6(7) . . ?
C6 C1 C7 120.7(14) . . ?
C4 C5 C6 121.0(7) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.8(14) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C1 C2 C3 124.1(7) . . ?
C1 C2 H2A 118.0 . . ?
C3 C2 H2A 118.0 . . ?
N3 C14 C13 112.6(5) . . ?
N3 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 115.5(5) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C11B C12 C13 111.5(11) . . ?
C11A C12 C13 127(6) . . ?
C11A C12 H12A 105.6 . . ?
C13 C12 H12A 105.6 . . ?
C11A C12 H12B 105.6 . . ?
C13 C12 H12B 105.6 . . ?
H12A C12 H12B 106.1 . . ?
C11B C12 H12C 109.3 . . ?
C13 C12 H12C 109.3 . . ?
C11B C12 H12D 109.3 . . ?
C13 C12 H12D 109.3 . . ?
H12C C12 H12D 108.0 . . ?
C10A C11A C12 92(6) . . ?
C10A C11A H11A 113.3 . . ?
C12 C11A H11A 113.3 . . ?
C10A C11A H11B 113.3 . . ?
C12 C11A H11B 113.3 . . ?
H11A C11A H11B 110.6 . . ?
C9 C10A C11A 137(10) . . ?
C9 C10A H10A 102.7 . . ?
C11A C10A H10A 102.7 . . ?
C9 C10A H10B 102.7 . . ?
C11A C10A H10B 102.7 . . ?
H10A C10A H10B 105.0 . . ?
C12 C11B C10B 112.8(6) . . ?
C12 C11B H11C 109.0 . . ?
C10B C11B H11C 109.0 . . ?
C12 C11B H11D 109.0 . . ?
C10B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
C9 C10B C11B 118.7(8) . . ?
C9 C10B H10C 107.6 . . ?
C11B C10B H10C 107.6 . . ?
C9 C10B H10D 107.6 . . ?
C11B C10B H10D 107.6 . . ?
H10C C10B H10D 107.1 . . ?
N3 C9 C10B 116.4(10) . . ?
N3 C9 C10A 96(6) . . ?
N3 C9 H9A 112.5 . . ?
C10A C9 H9A 112.5 . . ?
N3 C9 H9B 112.5 . . ?
C10A C9 H9B 112.5 . . ?
H9A C9 H9B 110.0 . . ?
N3 C9 H9C 108.2 . . ?
C10B C9 H9C 108.2 . . ?
N3 C9 H9D 108.2 . . ?
C10B C9 H9D 108.2 . . ?
H9C C9 H9D 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 41.5(7) . . . . ?
O1 S1 N1 C8 170.0(6) . . . . ?
C4 S1 N1 C8 -75.4(6) . . . . ?
O2 S1 C4 C5 10.1(8) . . . . ?
O1 S1 C4 C5 -119.8(7) . . . . ?
N1 S1 C4 C5 128.7(7) . . . . ?
O2 S1 C4 C3 -170.6(4) . . . . ?
O1 S1 C4 C3 59.6(6) . . . . ?
N1 S1 C4 C3 -52.0(5) . . . . ?
S1 N1 C8 O3 2.9(11) . . . . ?
S1 N1 C8 N2 -177.6(6) . . . . ?
C14 N3 N2 C8 120.1(8) . . . . ?
C9 N3 N2 C8 -111.2(8) . . . . ?
O3 C8 N2 N3 -176.1(7) . . . . ?
N1 C8 N2 N3 4.4(10) . . . . ?
C5 C4 C3 C2 2.6(10) . . . . ?
S1 C4 C3 C2 -176.7(4) . . . . ?
C3 C4 C5 C6 -1.8(12) . . . . ?
S1 C4 C5 C6 177.5(4) . . . . ?
C2 C1 C6 C5 0.4(11) . . . . ?
C7 C1 C6 C5 -179.6(5) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C6 C1 C2 C3 0.5(13) . . . . ?
C7 C1 C2 C3 -179.4(5) . . . . ?
C4 C3 C2 C1 -2.0(11) . . . . ?
N2 N3 C14 C13 -155.3(6) . . . . ?
C9 N3 C14 C13 80.6(6) . . . . ?
N3 C14 C13 C12 -83.5(10) . . . . ?
C14 C13 C12 C11B 62.8(9) . . . . ?
C14 C13 C12 C11A 30(7) . . . . ?
C13 C12 C11A C10A 28(12) . . . . ?
C12 C11A C10A C9 -107(15) . . . . ?
C13 C12 C11B C10B -66.7(10) . . . . ?
C12 C11B C10B C9 85.5(11) . . . . ?
N2 N3 C9 C10B -147.0(7) . . . . ?
C14 N3 C9 C10B -23.3(7) . . . . ?
N2 N3 C9 C10A -175(7) . . . . ?
C14 N3 C9 C10A -51(7) . . . . ?
C11B C10B C9 N3 -50.6(8) . . . . ?
C11A C10A C9 N3 100(14) . . . . ?

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
N1 H1 O1 0.86 2.14 2.863(7) 141.0 2_676
N2 H2 O3 0.86 2.03 2.868(5) 163.6 2_566

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1p01GPA
_database_code_depnum_ccdc_archive 'CCDC 1493070'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1p01GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.357 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.1901(4)
_cell_length_b                   8.6946(6)
_cell_length_c                   13.321(3)
_cell_angle_alpha                81.572(11)
_cell_angle_beta                 86.221(10)
_cell_angle_gamma                83.180(5)
_cell_volume                     703.33(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    839
_cell_measurement_theta_min      2.3760
_cell_measurement_theta_max      24.4030

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1010000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3542
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.340
_diffrn_measured_fraction_theta_full 0.357
_diffrn_reflns_Laue_measured_fraction_max 0.340
_diffrn_reflns_Laue_measured_fraction_full 0.357
_diffrn_reflns_point_group_measured_fraction_max 0.340
_diffrn_reflns_point_group_measured_fraction_full 0.357
_reflns_number_total             979
_reflns_number_gt                660
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         979
_refine_ls_number_parameters     210
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.828
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

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
S1 S 0.24408(18) 0.98232(15) 0.3914(3) 0.027(2) Uani 1 1 d . U . . .
O3 O 0.0546(6) 0.6760(4) 0.4149(8) 0.040(4) Uani 1 1 d . U . . .
N1 N 0.2580(6) 0.8357(4) 0.4835(9) 0.027(4) Uani 1 1 d . U . . .
H1 H 0.3319 0.8420 0.5349 0.033 Uiso 1 1 calc R U . . .
N3 N 0.3012(7) 0.6355(5) 0.6496(9) 0.031(4) Uani 1 1 d . U . . .
C4 C 0.4187(9) 0.9207(7) 0.2917(14) 0.027(3) Uani 1 1 d . U . . .
O2 O 0.0287(5) 1.0151(4) 0.3562(7) 0.030(5) Uani 1 1 d . U . . .
O1 O 0.3380(5) 1.1028(4) 0.4312(7) 0.032(5) Uani 1 1 d . U . . .
C8 C 0.1564(9) 0.7007(7) 0.4834(14) 0.029(4) Uani 1 1 d . U . . .
N2 N 0.1915(8) 0.5993(7) 0.5681(12) 0.038(4) Uani 1 1 d . U . . .
H2 H 0.1453 0.5089 0.5730 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6354(8) 0.8626(6) 0.3141(11) 0.028(5) Uani 1 1 d . U . . .
H3 H 0.6840 0.8537 0.3795 0.034 Uiso 1 1 calc R U . . .
C1 C 0.7030(10) 0.8360(8) 0.1330(16) 0.029(5) Uani 1 1 d . U . . .
C5 C 0.3453(10) 0.9318(8) 0.1971(15) 0.030(4) Uani 1 1 d . U . . .
H5 H 0.2008 0.9686 0.1849 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4835(8) 0.8890(6) 0.1202(13) 0.033(4) Uani 1 1 d . U . . .
H6 H 0.4295 0.8954 0.0561 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7698(10) 0.8202(8) 0.2358(15) 0.030(5) Uani 1 1 d . U . . .
H2A H 0.9122 0.7790 0.2492 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1556(8) 0.6326(7) 0.7427(12) 0.035(4) Uani 1 1 d . U . . .
H14A H 0.1588 0.5257 0.7764 0.042 Uiso 1 1 calc R U . . .
H14B H 0.0075 0.6675 0.7234 0.042 Uiso 1 1 calc R U . . .
C7 C 0.8513(10) 0.7892(8) 0.0473(14) 0.048(6) Uani 1 1 d . U . . .
H7A H 0.8573 0.8768 -0.0054 0.072 Uiso 1 1 calc R U . . .
H7B H 0.7975 0.7048 0.0209 0.072 Uiso 1 1 calc R U . . .
H7C H 0.9946 0.7558 0.0712 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2165(9) 0.7329(7) 0.8159(12) 0.046(5) Uani 1 1 d . U . . .
H13A H 0.0891 0.7579 0.8594 0.056 Uiso 1 1 calc R U . . .
H13B H 0.2551 0.8304 0.7777 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4019(10) 0.6637(8) 0.8828(14) 0.056(5) Uani 1 1 d D U . . .
H12A H 0.4901 0.7463 0.8897 0.068 Uiso 0.167(16) 1 calc R U P A 1
H12B H 0.3408 0.6278 0.9499 0.068 Uiso 0.167(16) 1 calc R U P A 1
H12C H 0.4230 0.7369 0.9287 0.068 Uiso 0.833(16) 1 calc R U P A 2
H12D H 0.3618 0.5686 0.9237 0.068 Uiso 0.833(16) 1 calc R U P A 2
C11A C 0.548(7) 0.531(4) 0.847(4) 0.054(9) Uani 0.167(16) 1 d D U P A 1
H11A H 0.6662 0.4995 0.8922 0.065 Uiso 0.167(16) 1 calc R U P A 1
H11B H 0.4664 0.4425 0.8469 0.065 Uiso 0.167(16) 1 calc R U P A 1
C10A C 0.637(6) 0.583(6) 0.742(3) 0.045(8) Uani 0.167(16) 1 d D U P A 1
H10A H 0.6344 0.6955 0.7313 0.053 Uiso 0.167(16) 1 calc R U P A 1
H10B H 0.7873 0.5378 0.7351 0.053 Uiso 0.167(16) 1 calc R U P A 1
C11B C 0.6130(12) 0.6265(12) 0.8249(15) 0.054(6) Uani 0.833(16) 1 d D U P A 2
H11C H 0.6484 0.7200 0.7806 0.065 Uiso 0.833(16) 1 calc R U P A 2
H11D H 0.7276 0.5970 0.8726 0.065 Uiso 0.833(16) 1 calc R U P A 2
C10B C 0.6086(14) 0.4981(10) 0.7624(11) 0.043(6) Uani 0.833(16) 1 d D U P A 2
H10C H 0.7575 0.4520 0.7521 0.052 Uiso 0.833(16) 1 calc R U P A 2
H10D H 0.5302 0.4181 0.8024 0.052 Uiso 0.833(16) 1 calc R U P A 2
C9 C 0.5113(9) 0.5351(7) 0.6605(12) 0.040(5) Uani 1 1 d D U . . .
H9A H 0.5960 0.5450 0.5965 0.047 Uiso 0.167(16) 1 calc R U P A 1
H9B H 0.4846 0.4265 0.6784 0.047 Uiso 0.167(16) 1 calc R U P A 1
H9C H 0.4932 0.4365 0.6380 0.047 Uiso 0.833(16) 1 calc R U P A 2
H9D H 0.6176 0.5843 0.6136 0.047 Uiso 0.833(16) 1 calc R U P A 2


_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
S1 O2 1.425(4) . ?
S1 O1 1.437(4) . ?
S1 N1 1.633(10) . ?
S1 C4 1.760(14) . ?
O3 C8 1.200(15) . ?
N1 C8 1.396(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.409(15) . ?
N3 C14 1.484(17) . ?
N3 C9 1.481(7) . ?
C4 C5 1.35(3) . ?
C4 C3 1.412(9) . ?
C8 N2 1.34(2) . ?
N2 H2 0.8600 . ?
C3 C2 1.357(19) . ?
C3 H3 0.9300 . ?
C1 C6 1.395(9) . ?
C1 C7 1.49(2) . ?
C1 C2 1.44(3) . ?
C5 C6 1.36(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.493(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.512(15) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11A 1.492(18) . ?
C12 C11B 1.499(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C11A C10A 1.498(18) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C10A C9 1.502(18) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11B C10B 1.491(14) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C10B C9 1.497(14) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C9 H9D 0.9700 . ?

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 S1 O1 118.7(2) . . ?
O2 S1 N1 110.6(3) . . ?
O1 S1 N1 104.1(5) . . ?
O2 S1 C4 108.3(5) . . ?
O1 S1 C4 108.4(3) . . ?
N1 S1 C4 106.0(5) . . ?
C8 N1 S1 123.6(9) . . ?
C8 N1 H1 118.2 . . ?
S1 N1 H1 118.2 . . ?
N2 N3 C14 110.6(6) . . ?
N2 N3 C9 110.0(7) . . ?
C14 N3 C9 115.3(10) . . ?
C5 C4 C3 122.0(13) . . ?
C5 C4 S1 120.3(6) . . ?
C3 C4 S1 117.7(12) . . ?
O3 C8 N2 123.8(7) . . ?
O3 C8 N1 124.4(13) . . ?
N2 C8 N1 111.7(12) . . ?
C8 N2 N3 122.4(6) . . ?
C8 N2 H2 118.8 . . ?
N3 N2 H2 118.8 . . ?
C2 C3 C4 116.9(13) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C6 C1 C7 122.0(15) . . ?
C6 C1 C2 114.8(15) . . ?
C7 C1 C2 123.1(8) . . ?
C4 C5 C6 119.7(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 123.0(15) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C3 C2 C1 123.3(7) . . ?
C3 C2 H2A 118.3 . . ?
C1 C2 H2A 118.3 . . ?
N3 C14 C13 113.5(6) . . ?
N3 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 116.1(5) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C11A C12 C13 116(3) . . ?
C11B C12 C13 113.8(12) . . ?
C11A C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11A C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C11B C12 H12C 108.8 . . ?
C13 C12 H12C 108.8 . . ?
C11B C12 H12D 108.8 . . ?
C13 C12 H12D 108.8 . . ?
H12C C12 H12D 107.7 . . ?
C10A C11A C12 109(3) . . ?
C10A C11A H11A 109.9 . . ?
C12 C11A H11A 109.9 . . ?
C10A C11A H11B 109.9 . . ?
C12 C11A H11B 109.9 . . ?
H11A C11A H11B 108.3 . . ?
C9 C10A C11A 113(4) . . ?
C9 C10A H10A 109.0 . . ?
C11A C10A H10A 109.0 . . ?
C9 C10A H10B 109.0 . . ?
C11A C10A H10B 109.0 . . ?
H10A C10A H10B 107.8 . . ?
C10B C11B C12 113.5(7) . . ?
C10B C11B H11C 108.9 . . ?
C12 C11B H11C 108.9 . . ?
C10B C11B H11D 108.9 . . ?
C12 C11B H11D 108.9 . . ?
H11C C11B H11D 107.7 . . ?
C9 C10B C11B 119.1(10) . . ?
C9 C10B H10C 107.6 . . ?
C11B C10B H10C 107.6 . . ?
C9 C10B H10D 107.6 . . ?
C11B C10B H10D 107.6 . . ?
H10C C10B H10D 107.0 . . ?
C10B C9 N3 119.5(10) . . ?
N3 C9 C10A 110.0(18) . . ?
N3 C9 H9A 109.7 . . ?
C10A C9 H9A 109.7 . . ?
N3 C9 H9B 109.7 . . ?
C10A C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10B C9 H9C 107.4 . . ?
N3 C9 H9C 107.4 . . ?
C10B C9 H9D 107.4 . . ?
N3 C9 H9D 107.4 . . ?
H9C C9 H9D 107.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 41.8(7) . . . . ?
O1 S1 N1 C8 170.5(6) . . . . ?
C4 S1 N1 C8 -75.3(7) . . . . ?
O2 S1 C4 C5 9.0(8) . . . . ?
O1 S1 C4 C5 -121.0(7) . . . . ?
N1 S1 C4 C5 127.7(8) . . . . ?
O2 S1 C4 C3 -171.9(5) . . . . ?
O1 S1 C4 C3 58.0(7) . . . . ?
N1 S1 C4 C3 -53.2(6) . . . . ?
S1 N1 C8 O3 2.3(11) . . . . ?
S1 N1 C8 N2 -179.4(6) . . . . ?
O3 C8 N2 N3 -176.3(7) . . . . ?
N1 C8 N2 N3 5.4(12) . . . . ?
C14 N3 N2 C8 117.8(9) . . . . ?
C9 N3 N2 C8 -113.6(9) . . . . ?
C5 C4 C3 C2 1.1(11) . . . . ?
S1 C4 C3 C2 -178.0(5) . . . . ?
C3 C4 C5 C6 -1.3(13) . . . . ?
S1 C4 C5 C6 177.7(5) . . . . ?
C4 C5 C6 C1 -1.3(12) . . . . ?
C7 C1 C6 C5 179.8(6) . . . . ?
C2 C1 C6 C5 3.8(12) . . . . ?
C4 C3 C2 C1 1.7(12) . . . . ?
C6 C1 C2 C3 -4.0(13) . . . . ?
C7 C1 C2 C3 -180.0(5) . . . . ?
N2 N3 C14 C13 -154.7(7) . . . . ?
C9 N3 C14 C13 79.8(7) . . . . ?
N3 C14 C13 C12 -80.1(12) . . . . ?
C14 C13 C12 C11A 19(2) . . . . ?
C14 C13 C12 C11B 60.8(11) . . . . ?
C13 C12 C11A C10A 56(4) . . . . ?
C12 C11A C10A C9 -97(5) . . . . ?
C13 C12 C11B C10B -66.6(12) . . . . ?
C12 C11B C10B C9 81.6(15) . . . . ?
C11B C10B C9 N3 -45.0(12) . . . . ?
N2 N3 C9 C10B -153.0(8) . . . . ?
C14 N3 C9 C10B -27.1(8) . . . . ?
N2 N3 C9 C10A 175(2) . . . . ?
C14 N3 C9 C10A -59(2) . . . . ?
C11A C10A C9 N3 75(3) . . . . ?

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
N1 H1 O1 0.86 2.24 2.950(7) 139.6 2_676
N2 H2 O3 0.86 2.12 2.961(5) 163.9 2_566

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_4p72GPA
_database_code_depnum_ccdc_archive 'CCDC 1493075'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_4p72GPA             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.343 Note
RESPONSE: Crystal loaded in diamond anvil cell
;
# Added during the CSD deposition process: Thursday 14 July 2016 06:45 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            tolazamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O3 S'
_chemical_formula_sum            'C14 H21 N3 O3 S'
_chemical_formula_weight         311.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.8398(3)
_cell_length_b                   8.2425(4)
_cell_length_c                   13.031(3)
_cell_angle_alpha                81.891(8)
_cell_angle_beta                 87.556(8)
_cell_angle_gamma                82.156(4)
_cell_volume                     614.97(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    942
_cell_measurement_theta_min      2.5130
_cell_measurement_theta_max      27.0220

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   
; Absorb7 and Absorb-GUI, Angel and Gonzalez-Platas (2013)
  J. Appl. Cryst. 46:252-254
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         4720000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3104
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.340
_diffrn_measured_fraction_theta_full 0.343
_diffrn_reflns_Laue_measured_fraction_max 0.340
_diffrn_reflns_Laue_measured_fraction_full 0.343
_diffrn_reflns_point_group_measured_fraction_max 0.340
_diffrn_reflns_point_group_measured_fraction_full 0.343
_reflns_number_total             856
_reflns_number_gt                641
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.0071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         856
_refine_ls_number_parameters     191
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      0.961
_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
S1 S 0.22820(17) 0.99581(14) 0.3900(3) 0.0142(19) Uani 1 1 d . U . . .
O3 O 0.0435(5) 0.6774(4) 0.4135(7) 0.019(3) Uani 1 1 d . U . . .
N1 N 0.2579(5) 0.8430(4) 0.4824(8) 0.016(3) Uani 1 1 d . U . . .
H1 H 0.3439 0.8501 0.5331 0.020 Uiso 1 1 calc R U . . .
N3 N 0.3141(6) 0.6340(5) 0.6514(9) 0.017(3) Uani 1 1 d . U . . .
C4 C 0.4046(8) 0.9303(7) 0.2890(14) 0.017(3) Uani 1 1 d . U . . .
O2 O -0.0024(4) 1.0291(3) 0.3543(6) 0.020(3) Uani 1 1 d . U . . .
O1 O 0.3236(5) 1.1258(4) 0.4294(7) 0.019(4) Uani 1 1 d . U . . .
C8 C 0.1542(8) 0.7006(6) 0.4856(12) 0.015(3) Uani 1 1 d . U . . .
N2 N 0.1978(7) 0.5942(6) 0.5708(10) 0.021(3) Uani 1 1 d . U . . .
H2 H 0.1524 0.4984 0.5758 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6322(7) 0.8654(5) 0.3115(10) 0.014(3) Uani 1 1 d . U . . .
H3 H 0.6856 0.8514 0.3788 0.016 Uiso 1 1 calc R U . . .
C1 C 0.7026(9) 0.8395(7) 0.1272(14) 0.016(4) Uani 1 1 d . U . . .
C5 C 0.3252(9) 0.9477(7) 0.1904(14) 0.016(3) Uani 1 1 d . U . . .
H5 H 0.1727 0.9921 0.1768 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4689(7) 0.9001(5) 0.1123(11) 0.017(3) Uani 1 1 d . U . . .
H6 H 0.4097 0.9081 0.0464 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7758(9) 0.8226(7) 0.2298(14) 0.014(4) Uani 1 1 d . U . . .
H2A H 0.9290 0.7804 0.2436 0.016 Uiso 1 1 calc R U . . .
C14 C 0.1598(7) 0.6230(6) 0.7486(11) 0.020(3) Uani 1 1 d . U . . .
H14A H 0.0001 0.6564 0.7290 0.025 Uiso 1 1 calc R U . . .
H14B H 0.1737 0.5091 0.7814 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8658(8) 0.7885(6) 0.0439(11) 0.020(4) Uani 1 1 d . U . . .
H7A H 0.9789 0.8637 0.0309 0.030 Uiso 1 1 calc R U . . .
H7B H 0.7824 0.7899 -0.0182 0.030 Uiso 1 1 calc R U . . .
H7C H 0.9419 0.6788 0.0651 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2190(7) 0.7278(6) 0.8238(10) 0.023(3) Uani 1 1 d . U . . .
H13A H 0.0814 0.7598 0.8644 0.028 Uiso 1 1 calc R U . . .
H13B H 0.2679 0.8278 0.7861 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4077(7) 0.6446(6) 0.8965(11) 0.027(4) Uani 1 1 d . U . . .
H12A H 0.3627 0.5420 0.9324 0.032 Uiso 1 1 calc R U . . .
H12B H 0.4266 0.7155 0.9481 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6370(7) 0.6080(6) 0.8387(11) 0.025(4) Uani 1 1 d . U . . .
H11A H 0.6741 0.7090 0.7976 0.030 Uiso 1 1 calc R U . . .
H11B H 0.7582 0.5711 0.8886 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6315(8) 0.4774(6) 0.7684(12) 0.019(4) Uani 1 1 d . U . . .
H10A H 0.7882 0.4224 0.7618 0.023 Uiso 1 1 calc R U . . .
H10B H 0.5400 0.3956 0.8036 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5413(8) 0.5276(6) 0.6622(12) 0.019(4) Uani 1 1 d . U . . .
H9A H 0.5296 0.4279 0.6322 0.023 Uiso 1 1 calc R U . . .
H9B H 0.6550 0.5854 0.6209 0.023 Uiso 1 1 calc R U . . .


_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
S1 O2 1.422(4) . ?
S1 O1 1.437(4) . ?
S1 N1 1.611(9) . ?
S1 C4 1.737(14) . ?
O3 C8 1.214(15) . ?
N1 C8 1.387(6) . ?
N1 H1 0.8600 . ?
N3 N2 1.375(14) . ?
N3 C9 1.488(6) . ?
N3 C14 1.522(16) . ?
C4 C5 1.37(3) . ?
C4 C3 1.390(8) . ?
C8 N2 1.324(18) . ?
N2 H2 0.8600 . ?
C3 C2 1.382(17) . ?
C3 H3 0.9300 . ?
C1 C6 1.400(7) . ?
C1 C2 1.40(3) . ?
C1 C7 1.481(16) . ?
C5 C6 1.357(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9300 . ?
C14 C13 1.474(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.511(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C11 1.523(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.513(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.49(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 S1 O1 118.11(18) . . ?
O2 S1 N1 111.7(3) . . ?
O1 S1 N1 104.6(4) . . ?
O2 S1 C4 107.5(5) . . ?
O1 S1 C4 109.1(3) . . ?
N1 S1 C4 105.1(5) . . ?
C8 N1 S1 124.4(8) . . ?
C8 N1 H1 117.8 . . ?
S1 N1 H1 117.8 . . ?
N2 N3 C9 109.4(7) . . ?
N2 N3 C14 109.0(5) . . ?
C9 N3 C14 114.5(10) . . ?
C5 C4 C3 121.2(12) . . ?
C5 C4 S1 121.3(5) . . ?
C3 C4 S1 117.5(12) . . ?
O3 C8 N2 125.1(6) . . ?
O3 C8 N1 121.2(11) . . ?
N2 C8 N1 113.6(10) . . ?
C8 N2 N3 121.3(5) . . ?
C8 N2 H2 119.3 . . ?
N3 N2 H2 119.3 . . ?
C2 C3 C4 117.3(12) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C6 C1 C2 115.3(13) . . ?
C6 C1 C7 124.3(13) . . ?
C2 C1 C7 120.4(7) . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 122.6(13) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
C3 C2 C1 123.5(6) . . ?
C3 C2 H2A 118.3 . . ?
C1 C2 H2A 118.3 . . ?
C13 C14 N3 112.6(5) . . ?
C13 C14 H14A 109.1 . . ?
N3 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
N3 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 C12 113.7(5) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C12 C11 111.6(10) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C10 C11 C12 112.4(5) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C9 C10 C11 119.2(6) . . ?
C9 C10 H10A 107.5 . . ?
C11 C10 H10A 107.5 . . ?
C9 C10 H10B 107.5 . . ?
C11 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C10 C9 N3 117.5(11) . . ?
C10 C9 H9A 107.9 . . ?
N3 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
N3 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 39.5(7) . . . . ?
O1 S1 N1 C8 168.4(6) . . . . ?
C4 S1 N1 C8 -76.8(6) . . . . ?
O2 S1 C4 C5 12.5(8) . . . . ?
O1 S1 C4 C5 -116.7(7) . . . . ?
N1 S1 C4 C5 131.6(7) . . . . ?
O2 S1 C4 C3 -169.9(4) . . . . ?
O1 S1 C4 C3 60.9(6) . . . . ?
N1 S1 C4 C3 -50.8(5) . . . . ?
S1 N1 C8 O3 5.0(10) . . . . ?
S1 N1 C8 N2 -177.9(6) . . . . ?
O3 C8 N2 N3 -176.4(7) . . . . ?
N1 C8 N2 N3 6.7(10) . . . . ?
C9 N3 N2 C8 -113.9(8) . . . . ?
C14 N3 N2 C8 120.2(7) . . . . ?
C5 C4 C3 C2 1.3(9) . . . . ?
S1 C4 C3 C2 -176.2(4) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
S1 C4 C5 C6 177.9(4) . . . . ?
C4 C5 C6 C1 -3.0(10) . . . . ?
C2 C1 C6 C5 3.4(10) . . . . ?
C7 C1 C6 C5 -179.2(5) . . . . ?
C4 C3 C2 C1 -0.8(10) . . . . ?
C6 C1 C2 C3 -1.4(11) . . . . ?
C7 C1 C2 C3 -179.0(4) . . . . ?
N2 N3 C14 C13 -155.1(6) . . . . ?
C9 N3 C14 C13 82.0(6) . . . . ?
N3 C14 C13 C12 -86.3(9) . . . . ?
C14 C13 C12 C11 64.8(8) . . . . ?
C13 C12 C11 C10 -67.7(8) . . . . ?
C12 C11 C10 C9 85.1(11) . . . . ?
C11 C10 C9 N3 -49.7(9) . . . . ?
N2 N3 C9 C10 -145.9(7) . . . . ?
C14 N3 C9 C10 -23.2(6) . . . . ?

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
N1 H1 O1 0.86 2.06 2.803(7) 143.5 2_676
N2 H2 O3 0.86 1.95 2.783(5) 162.3 2_566

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047

