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

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

data_compound-2
_database_code_depnum_ccdc_archive 'CCDC 1474053'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Cl N4 O'
_chemical_formula_sum            'C15 H19 Cl N4 O'
_chemical_formula_weight         306.79

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.987(2)
_cell_length_b                   16.528(3)
_cell_length_c                   20.406(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.626(17)
_cell_angle_gamma                90.00
_cell_volume                     4717.2(14)
_cell_formula_units_Z            12
_cell_measurement_temperature    165(2)
_cell_measurement_reflns_used    144
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      165(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         430
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            64918
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.50
_reflns_number_total             10616
_reflns_number_gt                6135
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.06P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10616
_refine_ls_number_parameters     572
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11606(5) 0.59236(4) 0.41861(3) 0.04526(19) Uani 1 1 d . . .
N3 N -0.20633(13) 0.72641(11) 0.86612(9) 0.0252(4) Uani 1 1 d . . .
O1 O -0.12960(10) 0.60290(8) 0.70269(7) 0.0245(4) Uani 1 1 d . . .
N1 N -0.02817(13) 0.70553(10) 0.67513(9) 0.0252(4) Uani 1 1 d . . .
H1A H -0.0017 0.7503 0.6900 0.030 Uiso 1 1 calc R . .
C6 C -0.01785(16) 0.60332(13) 0.51308(11) 0.0268(5) Uani 1 1 d . . .
H6A H -0.0568 0.5714 0.4847 0.032 Uiso 1 1 calc R . .
N2 N -0.12645(13) 0.71893(11) 0.76346(9) 0.0261(4) Uani 1 1 d . . .
H2B H -0.0962 0.7648 0.7710 0.031 Uiso 1 1 calc R . .
N4 N -0.28792(13) 0.70184(11) 0.89683(9) 0.0262(4) Uani 1 1 d . . .
C11 C -0.14115(17) 0.78199(14) 0.89917(12) 0.0316(6) Uani 1 1 d . . .
H11A H -0.0784 0.7795 0.8784 0.047 Uiso 1 1 calc R . .
H11B H -0.1348 0.7667 0.9454 0.047 Uiso 1 1 calc R . .
H11C H -0.1664 0.8372 0.8960 0.047 Uiso 1 1 calc R . .
C2 C 0.13167(17) 0.67019(13) 0.53537(11) 0.0289(6) Uani 1 1 d . . .
H2A H 0.1945 0.6842 0.5222 0.035 Uiso 1 1 calc R . .
C4 C 0.00477(16) 0.67530(12) 0.61479(11) 0.0230(5) Uani 1 1 d . . .
C7 C -0.09748(16) 0.67125(13) 0.71221(10) 0.0222(5) Uani 1 1 d . . .
C8 C -0.20231(16) 0.69728(13) 0.80416(11) 0.0242(5) Uani 1 1 d . . .
C3 C 0.09731(16) 0.69585(13) 0.59582(11) 0.0276(5) Uani 1 1 d . . .
H3A H 0.1369 0.7273 0.6241 0.033 Uiso 1 1 calc R . .
C10 C -0.33415(16) 0.65520(13) 0.85251(11) 0.0259(5) Uani 1 1 d . . .
C1 C 0.07365(17) 0.62416(13) 0.49476(11) 0.0280(5) Uani 1 1 d . . .
C12 C -0.43174(17) 0.62027(14) 0.86753(12) 0.0316(6) Uani 1 1 d . . .
C5 C -0.05292(16) 0.62907(12) 0.57286(11) 0.0245(5) Uani 1 1 d . . .
H5A H -0.1161 0.6153 0.5853 0.029 Uiso 1 1 calc R . .
C9 C -0.28206(16) 0.65064(13) 0.79406(11) 0.0271(5) Uani 1 1 d . . .
H9A H -0.2987 0.6213 0.7556 0.032 Uiso 1 1 calc R . .
C13 C -0.46279(19) 0.56319(16) 0.81246(14) 0.0451(7) Uani 1 1 d . . .
H13A H -0.4645 0.5928 0.7709 0.068 Uiso 1 1 calc R . .
H13B H -0.5266 0.5418 0.8217 0.068 Uiso 1 1 calc R . .
H13C H -0.4172 0.5183 0.8095 0.068 Uiso 1 1 calc R . .
C15 C -0.50192(19) 0.69149(17) 0.87337(16) 0.0524(8) Uani 1 1 d . . .
H15A H -0.5032 0.7220 0.8322 0.079 Uiso 1 1 calc R . .
H15B H -0.4812 0.7271 0.9092 0.079 Uiso 1 1 calc R . .
H15C H -0.5661 0.6708 0.8824 0.079 Uiso 1 1 calc R . .
C14 C -0.42993(19) 0.57304(17) 0.93245(13) 0.0475(7) Uani 1 1 d . . .
H14A H -0.4103 0.6092 0.9682 0.071 Uiso 1 1 calc R . .
H14B H -0.3845 0.5281 0.9293 0.071 Uiso 1 1 calc R . .
H14C H -0.4939 0.5517 0.9412 0.071 Uiso 1 1 calc R . .
Cl3 Cl -0.38573(5) 1.12666(4) 1.08656(4) 0.0489(2) Uani 1 1 d . . .
O3 O -0.24065(11) 0.73089(9) 1.12921(7) 0.0302(4) Uani 1 1 d . . .
N12 N -0.08302(13) 0.50029(10) 1.09367(9) 0.0269(5) Uani 1 1 d . . .
N9 N -0.30827(13) 0.77997(10) 1.03304(9) 0.0245(4) Uani 1 1 d . . .
H9B H -0.3266 0.7640 0.9937 0.029 Uiso 1 1 calc R . .
N11 N -0.10695(14) 0.57375(10) 1.06835(9) 0.0276(5) Uani 1 1 d . . .
N10 N -0.24391(14) 0.65380(11) 1.03641(9) 0.0317(5) Uani 1 1 d . . .
H10B H -0.2581 0.6531 0.9943 0.038 Uiso 1 1 calc R . .
C37 C -0.26255(15) 0.72265(13) 1.07119(11) 0.0234(5) Uani 1 1 d . . .
C34 C -0.32935(15) 0.86094(13) 1.04913(11) 0.0225(5) Uani 1 1 d . . .
C40 C -0.16650(16) 0.46405(13) 1.10605(10) 0.0222(5) Uani 1 1 d . . .
C38 C -0.20306(16) 0.58367(13) 1.06471(10) 0.0245(5) Uani 1 1 d . . .
C42 C -0.16969(16) 0.37830(13) 1.13305(11) 0.0262(5) Uani 1 1 d . . .
C33 C -0.36030(17) 0.91136(14) 0.99850(12) 0.0330(6) Uani 1 1 d . . .
H33A H -0.3686 0.8900 0.9556 0.040 Uiso 1 1 calc R . .
C44 C -0.2075(2) 0.32239(14) 1.07838(13) 0.0423(7) Uani 1 1 d . . .
H44A H -0.1644 0.3247 1.0409 0.063 Uiso 1 1 calc R . .
H44B H -0.2715 0.3401 1.0647 0.063 Uiso 1 1 calc R . .
H44C H -0.2106 0.2667 1.0948 0.063 Uiso 1 1 calc R . .
C31 C -0.36629(16) 1.02357(14) 1.07232(13) 0.0320(6) Uani 1 1 d . . .
C35 C -0.32013(17) 0.89247(14) 1.11201(11) 0.0316(6) Uani 1 1 d . . .
H35A H -0.3014 0.8583 1.1473 0.038 Uiso 1 1 calc R . .
C36 C -0.33833(17) 0.97408(14) 1.12326(12) 0.0340(6) Uani 1 1 d . . .
H36A H -0.3314 0.9957 1.1662 0.041 Uiso 1 1 calc R . .
C39 C -0.24336(16) 0.51470(13) 1.08889(11) 0.0264(5) Uani 1 1 d . . .
H39A H -0.3096 0.5034 1.0932 0.032 Uiso 1 1 calc R . .
C45 C -0.07003(19) 0.35062(15) 1.15463(14) 0.0454(7) Uani 1 1 d . . .
H45A H -0.0459 0.3864 1.1893 0.068 Uiso 1 1 calc R . .
H45B H -0.0269 0.3526 1.1172 0.068 Uiso 1 1 calc R . .
H45C H -0.0734 0.2951 1.1712 0.068 Uiso 1 1 calc R . .
C41 C -0.03247(18) 0.62886(14) 1.04663(14) 0.0411(7) Uani 1 1 d . . .
H41A H -0.0606 0.6819 1.0370 0.062 Uiso 1 1 calc R . .
H41B H -0.0028 0.6072 1.0070 0.062 Uiso 1 1 calc R . .
H41C H 0.0162 0.6345 1.0813 0.062 Uiso 1 1 calc R . .
C32 C -0.37921(18) 0.99271(15) 1.01012(13) 0.0381(7) Uani 1 1 d . . .
H32A H -0.4009 1.0267 0.9755 0.046 Uiso 1 1 calc R . .
C43 C -0.23646(19) 0.37467(15) 1.19193(12) 0.0393(6) Uani 1 1 d . . .
H43A H -0.2118 0.4100 1.2268 0.059 Uiso 1 1 calc R . .
H43B H -0.2399 0.3189 1.2081 0.059 Uiso 1 1 calc R . .
H43C H -0.3005 0.3928 1.1786 0.059 Uiso 1 1 calc R . .
Cl2 Cl 0.41689(4) 0.44170(4) 0.67554(3) 0.0458(2) Uani 1 1 d . . .
N5 N 0.00133(13) 0.47014(10) 0.72378(9) 0.0243(4) Uani 1 1 d . . .
H5B H -0.0247 0.5139 0.7068 0.029 Uiso 1 1 calc R . .
N7 N -0.22062(13) 0.42766(11) 0.87064(10) 0.0285(5) Uani 1 1 d . . .
C25 C -0.32811(16) 0.33768(14) 0.85206(12) 0.0281(5) Uani 1 1 d . . .
N8 N -0.29063(13) 0.38348(11) 0.89982(9) 0.0303(5) Uani 1 1 d . . .
C18 C 0.13965(17) 0.49584(13) 0.65816(11) 0.0263(5) Uani 1 1 d . . .
H18A H 0.0996 0.5248 0.6284 0.032 Uiso 1 1 calc R . .
C19 C 0.09962(16) 0.45819(12) 0.71286(11) 0.0232(5) Uani 1 1 d . . .
O2 O -0.03217(12) 0.35332(10) 0.77894(10) 0.0456(5) Uani 1 1 d . . .
N6 N -0.14689(13) 0.45012(11) 0.76653(9) 0.0298(5) Uani 1 1 d . . .
H6B H -0.1632 0.4956 0.7469 0.036 Uiso 1 1 calc R . .
C22 C -0.05707(17) 0.42016(13) 0.75823(11) 0.0269(5) Uani 1 1 d . . .
C20 C 0.15891(16) 0.41544(13) 0.75576(11) 0.0253(5) Uani 1 1 d . . .
H20A H 0.1328 0.3905 0.7935 0.030 Uiso 1 1 calc R . .
C21 C 0.25624(17) 0.40903(13) 0.74352(11) 0.0278(5) Uani 1 1 d . . .
H21A H 0.2964 0.3785 0.7721 0.033 Uiso 1 1 calc R . .
C24 C -0.28202(16) 0.35283(13) 0.79208(12) 0.0301(6) Uani 1 1 d . . .
H24A H -0.2954 0.3284 0.7508 0.036 Uiso 1 1 calc R . .
C16 C 0.29421(16) 0.44752(14) 0.68930(11) 0.0286(6) Uani 1 1 d . . .
C26 C -0.16953(17) 0.48939(14) 0.90787(12) 0.0348(6) Uani 1 1 d . . .
H26A H -0.1037 0.4933 0.8922 0.052 Uiso 1 1 calc R . .
H26B H -0.1688 0.4748 0.9544 0.052 Uiso 1 1 calc R . .
H26C H -0.2017 0.5416 0.9021 0.052 Uiso 1 1 calc R . .
C17 C 0.23647(17) 0.49136(13) 0.64698(11) 0.0291(6) Uani 1 1 d . . .
H17A H 0.2633 0.5183 0.6104 0.035 Uiso 1 1 calc R . .
C23 C -0.21429(16) 0.40986(13) 0.80585(11) 0.0260(5) Uani 1 1 d . . .
C27 C -0.41110(17) 0.28112(15) 0.86568(12) 0.0345(6) Uani 1 1 d U . .
C29 C -0.4985(2) 0.3111(2) 0.8307(2) 0.1101(18) Uani 1 1 d . . .
H29A H -0.5132 0.3660 0.8456 0.165 Uiso 1 1 calc R . .
H29B H -0.5524 0.2753 0.8403 0.165 Uiso 1 1 calc R . .
H29C H -0.4872 0.3116 0.7834 0.165 Uiso 1 1 calc R . .
C28 C -0.3863(2) 0.19631(18) 0.8421(2) 0.0838(13) Uani 1 1 d . . .
H28A H -0.3749 0.1975 0.7948 0.126 Uiso 1 1 calc R . .
H28B H -0.4395 0.1596 0.8513 0.126 Uiso 1 1 calc R . .
H28C H -0.3286 0.1773 0.8650 0.126 Uiso 1 1 calc R . .
C30 C -0.4279(3) 0.2748(2) 0.93924(17) 0.0911(13) Uani 1 1 d U . .
H30A H -0.4429 0.3284 0.9568 0.137 Uiso 1 1 calc R . .
H30B H -0.3701 0.2538 0.9609 0.137 Uiso 1 1 calc R . .
H30C H -0.4814 0.2380 0.9473 0.137 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
Cl1 C1 1.750(2) . ?
N3 C8 1.355(3) . ?
N3 N4 1.370(2) . ?
N3 C11 1.455(3) . ?
O1 C7 1.231(2) . ?
N1 C7 1.360(3) . ?
N1 C4 1.411(3) . ?
N1 H1A 0.8800 . ?
C6 C1 1.381(3) . ?
C6 C5 1.387(3) . ?
C6 H6A 0.9500 . ?
N2 C7 1.374(3) . ?
N2 C8 1.401(3) . ?
N2 H2B 0.8800 . ?
N4 C10 1.348(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 C1 1.382(3) . ?
C2 C3 1.395(3) . ?
C2 H2A 0.9500 . ?
C4 C3 1.397(3) . ?
C4 C5 1.397(3) . ?
C8 C9 1.370(3) . ?
C3 H3A 0.9500 . ?
C10 C9 1.407(3) . ?
C10 C12 1.516(3) . ?
C12 C13 1.527(3) . ?
C12 C14 1.537(4) . ?
C12 C15 1.538(3) . ?
C5 H5A 0.9500 . ?
C9 H9A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Cl3 C31 1.750(2) . ?
O3 C37 1.227(3) . ?
N12 C40 1.339(3) . ?
N12 N11 1.360(2) . ?
N9 C37 1.379(3) . ?
N9 C34 1.410(3) . ?
N9 H9B 0.8800 . ?
N11 C38 1.356(3) . ?
N11 C41 1.457(3) . ?
N10 C37 1.368(3) . ?
N10 C38 1.413(3) . ?
N10 H10B 0.8800 . ?
C34 C35 1.390(3) . ?
C34 C33 1.393(3) . ?
C40 C39 1.404(3) . ?
C40 C42 1.522(3) . ?
C38 C39 1.366(3) . ?
C42 C45 1.527(3) . ?
C42 C43 1.531(3) . ?
C42 C44 1.538(3) . ?
C33 C32 1.391(3) . ?
C33 H33A 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C31 C36 1.376(3) . ?
C31 C32 1.378(3) . ?
C35 C36 1.392(3) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
C39 H39A 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C32 H32A 0.9500 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
Cl2 C16 1.744(2) . ?
N5 C22 1.363(3) . ?
N5 C19 1.409(3) . ?
N5 H5B 0.8800 . ?
N7 C23 1.358(3) . ?
N7 N8 1.364(2) . ?
N7 C26 1.455(3) . ?
C25 N8 1.337(3) . ?
C25 C24 1.412(3) . ?
C25 C27 1.518(3) . ?
C18 C17 1.378(3) . ?
C18 C19 1.400(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.392(3) . ?
O2 C22 1.232(3) . ?
N6 C22 1.363(3) . ?
N6 C23 1.411(3) . ?
N6 H6B 0.8800 . ?
C20 C21 1.391(3) . ?
C20 H20A 0.9500 . ?
C21 C16 1.387(3) . ?
C21 H21A 0.9500 . ?
C24 C23 1.363(3) . ?
C24 H24A 0.9500 . ?
C16 C17 1.381(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C17 H17A 0.9500 . ?
C27 C29 1.493(4) . ?
C27 C28 1.523(4) . ?
C27 C30 1.525(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C8 N3 N4 111.41(18) . . ?
C8 N3 C11 128.7(2) . . ?
N4 N3 C11 119.75(17) . . ?
C7 N1 C4 125.42(18) . . ?
C7 N1 H1A 117.3 . . ?
C4 N1 H1A 117.3 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C7 N2 C8 122.43(18) . . ?
C7 N2 H2B 118.8 . . ?
C8 N2 H2B 118.8 . . ?
C10 N4 N3 104.98(17) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 N1 117.9(2) . . ?
C5 C4 N1 122.4(2) . . ?
O1 C7 N1 123.8(2) . . ?
O1 C7 N2 122.4(2) . . ?
N1 C7 N2 113.73(19) . . ?
N3 C8 C9 107.4(2) . . ?
N3 C8 N2 120.1(2) . . ?
C9 C8 N2 132.5(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
N4 C10 C9 110.5(2) . . ?
N4 C10 C12 120.5(2) . . ?
C9 C10 C12 128.8(2) . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 Cl1 119.32(18) . . ?
C2 C1 Cl1 119.69(18) . . ?
C10 C12 C13 109.63(19) . . ?
C10 C12 C14 111.2(2) . . ?
C13 C12 C14 108.8(2) . . ?
C10 C12 C15 107.5(2) . . ?
C13 C12 C15 110.7(2) . . ?
C14 C12 C15 109.1(2) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C8 C9 C10 105.7(2) . . ?
C8 C9 H9A 127.1 . . ?
C10 C9 H9A 127.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C40 N12 N11 105.04(17) . . ?
C37 N9 C34 128.14(18) . . ?
C37 N9 H9B 115.9 . . ?
C34 N9 H9B 115.9 . . ?
C38 N11 N12 111.63(17) . . ?
C38 N11 C41 128.31(19) . . ?
N12 N11 C41 120.00(19) . . ?
C37 N10 C38 123.30(19) . . ?
C37 N10 H10B 118.4 . . ?
C38 N10 H10B 118.4 . . ?
O3 C37 N10 123.1(2) . . ?
O3 C37 N9 125.3(2) . . ?
N10 C37 N9 111.63(19) . . ?
C35 C34 C33 119.0(2) . . ?
C35 C34 N9 123.6(2) . . ?
C33 C34 N9 117.3(2) . . ?
N12 C40 C39 110.68(19) . . ?
N12 C40 C42 120.94(19) . . ?
C39 C40 C42 128.3(2) . . ?
N11 C38 C39 106.98(19) . . ?
N11 C38 N10 121.2(2) . . ?
C39 C38 N10 131.7(2) . . ?
C40 C42 C45 110.68(19) . . ?
C40 C42 C43 109.95(18) . . ?
C45 C42 C43 109.0(2) . . ?
C40 C42 C44 107.95(19) . . ?
C45 C42 C44 109.5(2) . . ?
C43 C42 C44 109.8(2) . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33A 119.7 . . ?
C34 C33 H33A 119.7 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C36 C31 C32 120.6(2) . . ?
C36 C31 Cl3 119.77(19) . . ?
C32 C31 Cl3 119.62(19) . . ?
C34 C35 C36 120.0(2) . . ?
C34 C35 H35A 120.0 . . ?
C36 C35 H35A 120.0 . . ?
C31 C36 C35 120.1(2) . . ?
C31 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C38 C39 C40 105.7(2) . . ?
C38 C39 H39A 127.2 . . ?
C40 C39 H39A 127.2 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N11 C41 H41A 109.5 . . ?
N11 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N11 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C31 C32 C33 119.4(2) . . ?
C31 C32 H32A 120.3 . . ?
C33 C32 H32A 120.3 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C22 N5 C19 126.02(18) . . ?
C22 N5 H5B 117.0 . . ?
C19 N5 H5B 117.0 . . ?
C23 N7 N8 111.33(18) . . ?
C23 N7 C26 128.6(2) . . ?
N8 N7 C26 119.90(19) . . ?
N8 C25 C24 110.6(2) . . ?
N8 C25 C27 120.6(2) . . ?
C24 C25 C27 128.7(2) . . ?
C25 N8 N7 105.24(18) . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C20 C19 C18 119.1(2) . . ?
C20 C19 N5 123.2(2) . . ?
C18 C19 N5 117.6(2) . . ?
C22 N6 C23 121.45(19) . . ?
C22 N6 H6B 119.3 . . ?
C23 N6 H6B 119.3 . . ?
O2 C22 N5 123.5(2) . . ?
O2 C22 N6 122.7(2) . . ?
N5 C22 N6 113.74(19) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C16 C21 C20 119.5(2) . . ?
C16 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C23 C24 C25 105.5(2) . . ?
C23 C24 H24A 127.3 . . ?
C25 C24 H24A 127.3 . . ?
C17 C16 C21 120.9(2) . . ?
C17 C16 Cl2 119.85(18) . . ?
C21 C16 Cl2 119.28(18) . . ?
N7 C26 H26A 109.5 . . ?
N7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
N7 C23 C24 107.3(2) . . ?
N7 C23 N6 120.2(2) . . ?
C24 C23 N6 132.5(2) . . ?
C29 C27 C25 109.4(2) . . ?
C29 C27 C28 110.0(3) . . ?
C25 C27 C28 109.4(2) . . ?
C29 C27 C30 111.0(3) . . ?
C25 C27 C30 110.4(2) . . ?
C28 C27 C30 106.6(3) . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N3 N4 C10 1.0(2) . . . . ?
C11 N3 N4 C10 176.72(19) . . . . ?
C7 N1 C4 C3 -155.0(2) . . . . ?
C7 N1 C4 C5 27.8(3) . . . . ?
C4 N1 C7 O1 11.8(3) . . . . ?
C4 N1 C7 N2 -170.57(19) . . . . ?
C8 N2 C7 O1 -7.5(3) . . . . ?
C8 N2 C7 N1 174.80(19) . . . . ?
N4 N3 C8 C9 -1.5(2) . . . . ?
C11 N3 C8 C9 -176.7(2) . . . . ?
N4 N3 C8 N2 176.88(18) . . . . ?
C11 N3 C8 N2 1.7(3) . . . . ?
C7 N2 C8 N3 154.8(2) . . . . ?
C7 N2 C8 C9 -27.3(4) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
N1 C4 C3 C2 -177.37(19) . . . . ?
N3 N4 C10 C9 -0.2(2) . . . . ?
N3 N4 C10 C12 -176.51(19) . . . . ?
C5 C6 C1 C2 0.4(3) . . . . ?
C5 C6 C1 Cl1 -179.07(17) . . . . ?
C3 C2 C1 C6 0.1(3) . . . . ?
C3 C2 C1 Cl1 179.56(17) . . . . ?
N4 C10 C12 C13 -174.1(2) . . . . ?
C9 C10 C12 C13 10.3(3) . . . . ?
N4 C10 C12 C14 -53.8(3) . . . . ?
C9 C10 C12 C14 130.6(3) . . . . ?
N4 C10 C12 C15 65.5(3) . . . . ?
C9 C10 C12 C15 -110.1(3) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
N1 C4 C5 C6 177.74(19) . . . . ?
N3 C8 C9 C10 1.3(2) . . . . ?
N2 C8 C9 C10 -176.8(2) . . . . ?
N4 C10 C9 C8 -0.7(3) . . . . ?
C12 C10 C9 C8 175.3(2) . . . . ?
C40 N12 N11 C38 -0.1(2) . . . . ?
C40 N12 N11 C41 -177.6(2) . . . . ?
C38 N10 C37 O3 4.1(3) . . . . ?
C38 N10 C37 N9 -175.9(2) . . . . ?
C34 N9 C37 O3 7.8(4) . . . . ?
C34 N9 C37 N10 -172.3(2) . . . . ?
C37 N9 C34 C35 -10.9(3) . . . . ?
C37 N9 C34 C33 168.5(2) . . . . ?
N11 N12 C40 C39 -0.3(2) . . . . ?
N11 N12 C40 C42 177.92(18) . . . . ?
N12 N11 C38 C39 0.5(2) . . . . ?
C41 N11 C38 C39 177.7(2) . . . . ?
N12 N11 C38 N10 -176.36(18) . . . . ?
C41 N11 C38 N10 0.9(3) . . . . ?
C37 N10 C38 N11 -88.6(3) . . . . ?
C37 N10 C38 C39 95.5(3) . . . . ?
N12 C40 C42 C45 10.8(3) . . . . ?
C39 C40 C42 C45 -171.3(2) . . . . ?
N12 C40 C42 C43 131.2(2) . . . . ?
C39 C40 C42 C43 -50.9(3) . . . . ?
N12 C40 C42 C44 -109.1(2) . . . . ?
C39 C40 C42 C44 68.8(3) . . . . ?
C35 C34 C33 C32 1.8(3) . . . . ?
N9 C34 C33 C32 -177.7(2) . . . . ?
C33 C34 C35 C36 -2.4(4) . . . . ?
N9 C34 C35 C36 177.1(2) . . . . ?
C32 C31 C36 C35 1.8(4) . . . . ?
Cl3 C31 C36 C35 -178.21(19) . . . . ?
C34 C35 C36 C31 0.6(4) . . . . ?
N11 C38 C39 C40 -0.6(2) . . . . ?
N10 C38 C39 C40 175.7(2) . . . . ?
N12 C40 C39 C38 0.6(2) . . . . ?
C42 C40 C39 C38 -177.5(2) . . . . ?
C36 C31 C32 C33 -2.4(4) . . . . ?
Cl3 C31 C32 C33 177.66(18) . . . . ?
C34 C33 C32 C31 0.6(4) . . . . ?
C24 C25 N8 N7 -0.2(2) . . . . ?
C27 C25 N8 N7 -178.4(2) . . . . ?
C23 N7 N8 C25 0.0(2) . . . . ?
C26 N7 N8 C25 175.10(19) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C17 C18 C19 N5 175.52(19) . . . . ?
C22 N5 C19 C20 -28.0(3) . . . . ?
C22 N5 C19 C18 156.2(2) . . . . ?
C19 N5 C22 O2 -7.4(4) . . . . ?
C19 N5 C22 N6 174.0(2) . . . . ?
C23 N6 C22 O2 7.1(4) . . . . ?
C23 N6 C22 N5 -174.3(2) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
N5 C19 C20 C21 -177.1(2) . . . . ?
C19 C20 C21 C16 1.9(3) . . . . ?
N8 C25 C24 C23 0.3(3) . . . . ?
C27 C25 C24 C23 178.3(2) . . . . ?
C20 C21 C16 C17 -0.7(3) . . . . ?
C20 C21 C16 Cl2 178.15(17) . . . . ?
C19 C18 C17 C16 1.7(3) . . . . ?
C21 C16 C17 C18 -1.1(3) . . . . ?
Cl2 C16 C17 C18 -179.90(17) . . . . ?
N8 N7 C23 C24 0.2(3) . . . . ?
C26 N7 C23 C24 -174.4(2) . . . . ?
N8 N7 C23 N6 179.07(18) . . . . ?
C26 N7 C23 N6 4.4(3) . . . . ?
C25 C24 C23 N7 -0.3(3) . . . . ?
C25 C24 C23 N6 -178.9(2) . . . . ?
C22 N6 C23 N7 90.6(3) . . . . ?
C22 N6 C23 C24 -90.9(3) . . . . ?
N8 C25 C27 C29 112.0(3) . . . . ?
C24 C25 C27 C29 -65.9(4) . . . . ?
N8 C25 C27 C28 -127.5(3) . . . . ?
C24 C25 C27 C28 54.7(4) . . . . ?
N8 C25 C27 C30 -10.5(3) . . . . ?
C24 C25 C27 C30 171.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.060

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' tm in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            438.36
_reflns_d_resolution_high        0.7696
####################################################################### 
# 
# 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_compound-3-MeOH-solvate
_database_code_depnum_ccdc_archive 'CCDC 1474054'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 Cl N4 O, C H4 O'
_chemical_formula_sum            'C21 H25 Cl N4 O2'
_chemical_formula_weight         400.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2894(15)
_cell_length_b                   16.911(3)
_cell_length_c                   9.2595(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.917(9)
_cell_angle_gamma                90.00
_cell_volume                     2061.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    161(2)
_cell_measurement_reflns_used    199
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      161(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         369
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            34134
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         30.50
_reflns_number_total             6244
_reflns_number_gt                4556
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.04P)²+0.8P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6244
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.54400(3) 0.44605(2) 0.67300(5) 0.03594(10) Uani 1 1 d . . .
O1 O 0.07962(7) 0.26475(6) 0.67688(9) 0.0235(2) Uani 1 1 d . . .
N4 N 0.15885(8) 0.27828(7) 0.47320(12) 0.0205(2) Uani 1 1 d . . .
N1 N -0.12901(8) 0.12935(6) 0.44278(11) 0.0202(2) Uani 1 1 d . . .
N3 N -0.00201(8) 0.23002(7) 0.45221(12) 0.0233(2) Uani 1 1 d . . .
N2 N -0.21659(8) 0.11105(6) 0.49843(12) 0.0214(2) Uani 1 1 d . . .
C14 C 0.07962(9) 0.25837(7) 0.54426(13) 0.0182(2) Uani 1 1 d . . .
C18 C 0.43227(9) 0.39346(8) 0.61944(15) 0.0240(3) Uani 1 1 d . . .
C1 C -0.22826(9) 0.16826(7) 0.59366(13) 0.0195(2) Uani 1 1 d . . .
C15 C 0.25100(9) 0.31506(7) 0.53155(13) 0.0182(2) Uani 1 1 d . . .
C4 C -0.31600(10) 0.16570(8) 0.68236(15) 0.0235(3) Uani 1 1 d . . .
C17 C 0.35606(10) 0.39565(8) 0.70652(14) 0.0236(3) Uani 1 1 d . . .
H17 H 0.3661 0.4236 0.7964 0.028 Uiso 1 1 calc R . .
C8 C -0.09609(10) 0.07747(7) 0.33694(14) 0.0211(3) Uani 1 1 d . . .
C2 C -0.14939(10) 0.22470(8) 0.59853(14) 0.0216(3) Uani 1 1 d . . .
C16 C 0.26442(10) 0.35697(8) 0.66280(14) 0.0214(3) Uani 1 1 d . . .
H16 H 0.2114 0.3591 0.7218 0.026 Uiso 1 1 calc R . .
C3 C -0.08808(9) 0.19799(8) 0.50085(13) 0.0201(2) Uani 1 1 d . . .
C13 C -0.16771(11) 0.04990(8) 0.22500(15) 0.0281(3) Uani 1 1 d . . .
H13A H -0.2354 0.0693 0.2140 0.034 Uiso 1 1 calc R . .
C20 C 0.33010(10) 0.31174(8) 0.44704(15) 0.0238(3) Uani 1 1 d . . .
H20 H 0.3219 0.2820 0.3591 0.029 Uiso 1 1 calc R . .
C9 C 0.00398(11) 0.05193(9) 0.35165(16) 0.0288(3) Uani 1 1 d . . .
H9A H 0.0530 0.0724 0.4268 0.035 Uiso 1 1 calc R . .
C19 C 0.42055(10) 0.35142(8) 0.49021(16) 0.0270(3) Uani 1 1 d . . .
H19 H 0.4738 0.3497 0.4316 0.032 Uiso 1 1 calc R . .
C6 C -0.34319(12) 0.24987(9) 0.72335(18) 0.0342(3) Uani 1 1 d . . .
H6A H -0.2853 0.2736 0.7853 0.051 Uiso 1 1 calc R . .
H6B H -0.4021 0.2484 0.7764 0.051 Uiso 1 1 calc R . .
H6C H -0.3596 0.2815 0.6346 0.051 Uiso 1 1 calc R . .
C7 C -0.28292(12) 0.11760(10) 0.82187(17) 0.0344(3) Uani 1 1 d . . .
H7A H -0.2687 0.0630 0.7957 0.052 Uiso 1 1 calc R . .
H7B H -0.3375 0.1180 0.8831 0.052 Uiso 1 1 calc R . .
H7C H -0.2215 0.1412 0.8757 0.052 Uiso 1 1 calc R . .
C10 C 0.03122(13) -0.00417(10) 0.25436(18) 0.0387(4) Uani 1 1 d . . .
H10A H 0.0995 -0.0222 0.2628 0.046 Uiso 1 1 calc R . .
C11 C -0.04034(15) -0.03397(10) 0.14535(19) 0.0421(4) Uani 1 1 d . . .
H11A H -0.0215 -0.0736 0.0814 0.050 Uiso 1 1 calc R . .
C5 C -0.40894(11) 0.12629(10) 0.59429(18) 0.0364(4) Uani 1 1 d . . .
H5A H -0.4311 0.1576 0.5066 0.055 Uiso 1 1 calc R . .
H5B H -0.4642 0.1233 0.6541 0.055 Uiso 1 1 calc R . .
H5C H -0.3909 0.0729 0.5660 0.055 Uiso 1 1 calc R . .
C12 C -0.13904(14) -0.00641(9) 0.12918(17) 0.0381(4) Uani 1 1 d . . .
H12A H -0.1875 -0.0260 0.0524 0.046 Uiso 1 1 calc R . .
H2A H -0.1409(12) 0.2736(10) 0.6517(17) 0.028(4) Uiso 1 1 d . . .
H4 H 0.1535(12) 0.2670(10) 0.3847(19) 0.028(4) Uiso 1 1 d . . .
H3 H 0.0035(13) 0.2257(10) 0.362(2) 0.036(5) Uiso 1 1 d . . .
O2 O -0.24817(10) -0.05568(7) 0.52329(13) 0.0421(3) Uani 1 1 d . . .
C21 C -0.28942(15) -0.09778(10) 0.3994(2) 0.0466(4) Uani 1 1 d . . .
H21A H -0.3173 -0.1480 0.4289 0.070 Uiso 1 1 calc R . .
H21B H -0.2362 -0.1083 0.3384 0.070 Uiso 1 1 calc R . .
H21C H -0.3437 -0.0666 0.3439 0.070 Uiso 1 1 calc R . .
H2B H -0.2455(15) -0.0073(13) 0.503(2) 0.052(6) Uiso 1 1 d . . .


_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
Cl C18 1.7432(13) . ?
O1 C14 1.2327(15) . ?
N4 C14 1.3586(16) . ?
N4 C15 1.4129(15) . ?
N4 H4 0.834(17) . ?
N1 C3 1.3608(16) . ?
N1 N2 1.3715(14) . ?
N1 C8 1.4282(16) . ?
N3 C14 1.3706(16) . ?
N3 C3 1.3951(16) . ?
N3 H3 0.856(18) . ?
N2 C1 1.3323(16) . ?
C18 C17 1.3791(19) . ?
C18 C19 1.3821(19) . ?
C1 C2 1.4137(17) . ?
C1 C4 1.5165(17) . ?
C15 C20 1.3953(18) . ?
C15 C16 1.3969(17) . ?
C4 C6 1.529(2) . ?
C4 C5 1.5353(19) . ?
C4 C7 1.539(2) . ?
C17 C16 1.3925(18) . ?
C17 H17 0.9500 . ?
C8 C9 1.3870(19) . ?
C8 C13 1.3877(19) . ?
C2 C3 1.3744(18) . ?
C2 H2A 0.961(16) . ?
C16 H16 0.9500 . ?
C13 C12 1.390(2) . ?
C13 H13A 0.9500 . ?
C20 C19 1.3865(18) . ?
C20 H20 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9500 . ?
C19 H19 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 C11 1.383(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11A 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C12 H12A 0.9500 . ?
O2 C21 1.396(2) . ?
O2 H2B 0.84(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C14 N4 C15 127.78(11) . . ?
C14 N4 H4 116.9(11) . . ?
C15 N4 H4 115.3(11) . . ?
C3 N1 N2 110.96(10) . . ?
C3 N1 C8 130.66(10) . . ?
N2 N1 C8 118.38(10) . . ?
C14 N3 C3 123.30(11) . . ?
C14 N3 H3 118.2(12) . . ?
C3 N3 H3 117.9(12) . . ?
C1 N2 N1 105.49(10) . . ?
O1 C14 N4 124.55(11) . . ?
O1 C14 N3 122.78(11) . . ?
N4 C14 N3 112.67(11) . . ?
C17 C18 C19 121.05(12) . . ?
C17 C18 Cl 119.03(10) . . ?
C19 C18 Cl 119.92(11) . . ?
N2 C1 C2 110.97(11) . . ?
N2 C1 C4 120.40(11) . . ?
C2 C1 C4 128.60(11) . . ?
C20 C15 C16 119.51(11) . . ?
C20 C15 N4 116.62(11) . . ?
C16 C15 N4 123.79(11) . . ?
C1 C4 C6 109.48(11) . . ?
C1 C4 C5 110.30(11) . . ?
C6 C4 C5 109.60(12) . . ?
C1 C4 C7 108.52(11) . . ?
C6 C4 C7 109.50(12) . . ?
C5 C4 C7 109.41(12) . . ?
C18 C17 C16 120.05(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C9 C8 C13 121.23(13) . . ?
C9 C8 N1 120.27(12) . . ?
C13 C8 N1 118.39(12) . . ?
C3 C2 C1 105.15(11) . . ?
C3 C2 H2A 125.6(9) . . ?
C1 C2 H2A 129.1(9) . . ?
C17 C16 C15 119.53(12) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N1 C3 C2 107.42(11) . . ?
N1 C3 N3 120.30(11) . . ?
C2 C3 N3 132.19(12) . . ?
C8 C13 C12 119.13(14) . . ?
C8 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C19 C20 C15 120.59(12) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C8 C9 C10 118.72(14) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C18 C19 C20 119.23(12) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C10 C9 120.49(15) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C12 C11 C10 120.24(14) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C12 C13 120.12(15) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C21 O2 H2B 109.4(14) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 -1.21(14) . . . . ?
C8 N1 N2 C1 179.56(11) . . . . ?
C15 N4 C14 O1 -5.5(2) . . . . ?
C15 N4 C14 N3 174.40(12) . . . . ?
C3 N3 C14 O1 -7.1(2) . . . . ?
C3 N3 C14 N4 173.00(12) . . . . ?
N1 N2 C1 C2 1.02(14) . . . . ?
N1 N2 C1 C4 -177.39(11) . . . . ?
C14 N4 C15 C20 164.57(13) . . . . ?
C14 N4 C15 C16 -18.8(2) . . . . ?
N2 C1 C4 C6 -152.98(12) . . . . ?
C2 C1 C4 C6 28.92(19) . . . . ?
N2 C1 C4 C5 -32.29(17) . . . . ?
C2 C1 C4 C5 149.60(14) . . . . ?
N2 C1 C4 C7 87.55(15) . . . . ?
C2 C1 C4 C7 -90.55(16) . . . . ?
C19 C18 C17 C16 -1.8(2) . . . . ?
Cl C18 C17 C16 177.17(10) . . . . ?
C3 N1 C8 C9 49.28(19) . . . . ?
N2 N1 C8 C9 -131.66(13) . . . . ?
C3 N1 C8 C13 -134.47(14) . . . . ?
N2 N1 C8 C13 44.58(17) . . . . ?
N2 C1 C2 C3 -0.48(15) . . . . ?
C4 C1 C2 C3 177.77(12) . . . . ?
C18 C17 C16 C15 1.00(19) . . . . ?
C20 C15 C16 C17 0.79(19) . . . . ?
N4 C15 C16 C17 -175.73(12) . . . . ?
N2 N1 C3 C2 0.93(14) . . . . ?
C8 N1 C3 C2 -179.96(12) . . . . ?
N2 N1 C3 N3 -175.97(11) . . . . ?
C8 N1 C3 N3 3.1(2) . . . . ?
C1 C2 C3 N1 -0.28(14) . . . . ?
C1 C2 C3 N3 176.11(13) . . . . ?
C14 N3 C3 N1 -134.55(13) . . . . ?
C14 N3 C3 C2 49.4(2) . . . . ?
C9 C8 C13 C12 2.3(2) . . . . ?
N1 C8 C13 C12 -173.93(12) . . . . ?
C16 C15 C20 C19 -1.8(2) . . . . ?
N4 C15 C20 C19 174.96(12) . . . . ?
C13 C8 C9 C10 -2.0(2) . . . . ?
N1 C8 C9 C10 174.12(13) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
Cl C18 C19 C20 -178.17(11) . . . . ?
C15 C20 C19 C18 1.0(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 2.1(2) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
C8 C13 C12 C11 -0.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' trans in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            166.25
_reflns_d_resolution_high        0.7002
####################################################################### 
# 
# 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_compound-3-DMSO-solvate
_database_code_depnum_ccdc_archive 'CCDC 1474055'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 Cl N4 O, C2 H6 S O'
_chemical_formula_sum            'C22 H27 Cl N4 O2 S'
_chemical_formula_weight         446.99

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.217(3)
_cell_length_b                   15.177(4)
_cell_length_c                   16.060(4)
_cell_angle_alpha                72.646(9)
_cell_angle_beta                 85.659(14)
_cell_angle_gamma                88.367(10)
_cell_volume                     2370.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    107
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         138
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            26548
_diffrn_reflns_av_R_equivalents  0.1489
_diffrn_reflns_av_sigmaI/netI    0.2843
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         26.75
_reflns_number_total             9835
_reflns_number_gt                3214
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.06P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9835
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2539
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.33188(16) 0.25194(11) 0.10894(9) 0.0672(5) Uani 1 1 d . . .
Cl2 Cl -0.15964(19) 0.43421(11) 0.11470(10) 0.0796(6) Uani 1 1 d . . .
N7 N -0.0939(5) 0.3662(3) 0.6280(3) 0.0353(12) Uani 1 1 d . . .
O2 O -0.2710(4) 0.3908(2) 0.5442(2) 0.0456(10) Uani 1 1 d . . .
O1 O 0.2216(4) 0.0825(2) 0.5489(2) 0.0457(10) Uani 1 1 d . . .
N5 N -0.1011(4) 0.3520(3) 0.7786(3) 0.0302(10) Uani 1 1 d . . .
N1 N 0.3892(4) 0.0080(3) 0.7865(3) 0.0309(10) Uani 1 1 d . . .
N3 N 0.3994(5) 0.0631(3) 0.6300(3) 0.0347(12) Uani 1 1 d . . .
N6 N -0.1754(4) 0.3780(3) 0.8420(3) 0.0337(11) Uani 1 1 d . . .
N2 N 0.3167(4) -0.0480(3) 0.8564(3) 0.0329(11) Uani 1 1 d . . .
C21 C -0.2780(5) 0.4226(3) 0.8019(3) 0.0307(13) Uani 1 1 d . . .
C17 C 0.2541(5) 0.2246(3) 0.2798(4) 0.0390(14) Uani 1 1 d . . .
H17A H 0.1700 0.2458 0.2606 0.047 Uiso 1 1 calc R . .
C23 C -0.1544(5) 0.3808(3) 0.7012(3) 0.0267(12) Uani 1 1 d . . .
N4 N 0.4218(5) 0.1393(3) 0.4842(3) 0.0373(12) Uani 1 1 d . . .
C2 C 0.2256(5) -0.0385(3) 0.7305(3) 0.0322(13) Uani 1 1 d . . .
H2A H 0.1660 -0.0476 0.6912 0.039 Uiso 1 1 calc R . .
N8 N -0.0660(5) 0.3631(3) 0.4861(3) 0.0359(12) Uani 1 1 d . . .
C3 C 0.3392(5) 0.0148(3) 0.7089(3) 0.0290(13) Uani 1 1 d . . .
C15 C 0.3959(5) 0.1672(3) 0.3970(3) 0.0313(13) Uani 1 1 d . . .
C40 C 0.0077(5) 0.4087(3) 0.3363(3) 0.0358(14) Uani 1 1 d . . .
H40A H 0.0916 0.4188 0.3535 0.043 Uiso 1 1 calc R . .
C35 C -0.0923(5) 0.3776(3) 0.3986(3) 0.0312(13) Uani 1 1 d . . .
C1 C 0.2170(5) -0.0757(3) 0.8212(3) 0.0299(13) Uani 1 1 d . . .
C24 C -0.3845(5) 0.4585(4) 0.8526(3) 0.0351(13) Uani 1 1 d . . .
C16 C 0.2732(5) 0.1988(3) 0.3674(4) 0.0393(14) Uani 1 1 d . . .
H16A H 0.2025 0.2023 0.4082 0.047 Uiso 1 1 calc R . .
C20 C 0.4978(5) 0.1652(3) 0.3348(3) 0.0350(13) Uani 1 1 d . . .
H20A H 0.5825 0.1455 0.3538 0.042 Uiso 1 1 calc R . .
C18 C 0.3554(6) 0.2204(3) 0.2189(3) 0.0406(14) Uani 1 1 d . . .
C22 C -0.2696(5) 0.4260(3) 0.7131(3) 0.0311(13) Uani 1 1 d . . .
H22A H -0.3302 0.4537 0.6707 0.037 Uiso 1 1 calc R . .
C7 C 0.1817(5) -0.2146(4) 0.9490(3) 0.0590(18) Uani 1 1 d . . .
H7A H 0.2346 -0.1875 0.9835 0.088 Uiso 1 1 calc R . .
H7B H 0.2385 -0.2510 0.9197 0.088 Uiso 1 1 calc R . .
H7C H 0.1146 -0.2546 0.9878 0.088 Uiso 1 1 calc R . .
C37 C -0.2318(6) 0.3737(4) 0.2869(4) 0.0491(16) Uani 1 1 d . . .
H37A H -0.3137 0.3593 0.2698 0.059 Uiso 1 1 calc R . .
C36 C -0.2144(5) 0.3573(4) 0.3752(4) 0.0465(15) Uani 1 1 d . . .
H36A H -0.2834 0.3331 0.4184 0.056 Uiso 1 1 calc R . .
C33 C 0.0906(5) 0.3231(4) 0.8615(3) 0.0380(14) Uani 1 1 d . . .
H33A H 0.0671 0.3744 0.8821 0.046 Uiso 1 1 calc R . .
C28 C 0.0166(5) 0.3010(4) 0.8031(3) 0.0325(13) Uani 1 1 d . . .
C34 C -0.1536(6) 0.3759(3) 0.5511(4) 0.0362(14) Uani 1 1 d . . .
C4 C 0.1153(5) -0.1376(4) 0.8806(3) 0.0355(14) Uani 1 1 d . . .
C14 C 0.3380(6) 0.0933(3) 0.5541(4) 0.0313(13) Uani 1 1 d . . .
C29 C 0.0506(5) 0.2241(4) 0.7746(3) 0.0403(14) Uani 1 1 d . . .
H29A H -0.0021 0.2067 0.7359 0.048 Uiso 1 1 calc R . .
C19 C 0.4798(6) 0.1906(4) 0.2477(4) 0.0430(15) Uani 1 1 d . . .
H19A H 0.5509 0.1881 0.2068 0.052 Uiso 1 1 calc R . .
C8 C 0.5048(5) 0.0508(4) 0.8052(3) 0.0348(14) Uani 1 1 d . . .
C30 C 0.1613(6) 0.1743(4) 0.8036(4) 0.0497(16) Uani 1 1 d . . .
H30A H 0.1865 0.1236 0.7824 0.060 Uiso 1 1 calc R . .
C32 C 0.1997(5) 0.2702(4) 0.8902(3) 0.0470(16) Uani 1 1 d . . .
H32A H 0.2510 0.2859 0.9306 0.056 Uiso 1 1 calc R . .
C38 C -0.1346(7) 0.4096(4) 0.2242(4) 0.0449(15) Uani 1 1 d . . .
C10 C 0.6454(6) 0.1791(4) 0.7797(4) 0.0550(17) Uani 1 1 d . . .
H10A H 0.6726 0.2392 0.7459 0.066 Uiso 1 1 calc R . .
C13 C 0.5708(5) 0.0033(4) 0.8752(3) 0.0447(15) Uani 1 1 d . . .
H13A H 0.5445 -0.0574 0.9081 0.054 Uiso 1 1 calc R . .
C9 C 0.5378(5) 0.1392(4) 0.7561(4) 0.0441(15) Uani 1 1 d . . .
H9A H 0.4895 0.1720 0.7080 0.053 Uiso 1 1 calc R . .
C39 C -0.0110(6) 0.4261(3) 0.2479(4) 0.0515(16) Uani 1 1 d . . .
H39A H 0.0587 0.4487 0.2047 0.062 Uiso 1 1 calc R . .
C11 C 0.7120(6) 0.1328(5) 0.8506(4) 0.064(2) Uani 1 1 d . . .
H11A H 0.7826 0.1618 0.8672 0.077 Uiso 1 1 calc R . .
C5 C 0.0320(5) -0.1804(4) 0.8283(3) 0.0593(18) Uani 1 1 d . . .
H5A H -0.0126 -0.1314 0.7853 0.089 Uiso 1 1 calc R . .
H5B H -0.0334 -0.2212 0.8679 0.089 Uiso 1 1 calc R . .
H5C H 0.0885 -0.2161 0.7980 0.089 Uiso 1 1 calc R . .
C31 C 0.2360(6) 0.1954(4) 0.8619(4) 0.0531(17) Uani 1 1 d . . .
H31A H 0.3112 0.1594 0.8823 0.064 Uiso 1 1 calc R . .
C25 C -0.4466(6) 0.5444(4) 0.7933(4) 0.070(2) Uani 1 1 d . . .
H25A H -0.3797 0.5923 0.7703 0.105 Uiso 1 1 calc R . .
H25B H -0.5168 0.5671 0.8267 0.105 Uiso 1 1 calc R . .
H25C H -0.4831 0.5292 0.7446 0.105 Uiso 1 1 calc R . .
C27 C -0.3291(5) 0.4827(5) 0.9274(4) 0.070(2) Uani 1 1 d . . .
H27A H -0.2902 0.4274 0.9665 0.106 Uiso 1 1 calc R . .
H27B H -0.3996 0.5063 0.9599 0.106 Uiso 1 1 calc R . .
H27C H -0.2615 0.5300 0.9044 0.106 Uiso 1 1 calc R . .
C12 C 0.6765(6) 0.0435(5) 0.8984(4) 0.0649(19) Uani 1 1 d . . .
H12A H 0.7243 0.0103 0.9466 0.078 Uiso 1 1 calc R . .
C6 C 0.0263(6) -0.0822(4) 0.9255(4) 0.081(2) Uani 1 1 d . . .
H6A H 0.0781 -0.0549 0.9604 0.121 Uiso 1 1 calc R . .
H6B H -0.0408 -0.1226 0.9638 0.121 Uiso 1 1 calc R . .
H6C H -0.0162 -0.0329 0.8815 0.121 Uiso 1 1 calc R . .
C26 C -0.4898(6) 0.3859(4) 0.8880(4) 0.080(2) Uani 1 1 d . . .
H26A H -0.4516 0.3304 0.9272 0.119 Uiso 1 1 calc R . .
H26B H -0.5259 0.3705 0.8393 0.119 Uiso 1 1 calc R . .
H26C H -0.5601 0.4100 0.9204 0.119 Uiso 1 1 calc R . .
H3 H 0.480(4) 0.069(3) 0.625(3) 0.026(16) Uiso 1 1 d . . .
H7D H -0.010(5) 0.363(3) 0.621(3) 0.038(17) Uiso 1 1 d . . .
H8 H 0.012(5) 0.364(3) 0.497(3) 0.042(18) Uiso 1 1 d . . .
H4 H 0.498(5) 0.128(4) 0.499(3) 0.05(2) Uiso 1 1 d . . .
S1 S 0.31088(14) 0.32264(10) 0.58664(9) 0.0432(4) Uani 1 1 d . . .
O3 O 0.1734(3) 0.3481(3) 0.5636(2) 0.0605(12) Uani 1 1 d . . .
C41 C 0.4107(5) 0.3786(4) 0.4929(3) 0.0515(16) Uani 1 1 d . . .
H41A H 0.4024 0.3480 0.4477 0.077 Uiso 1 1 calc R . .
H41B H 0.5024 0.3757 0.5076 0.077 Uiso 1 1 calc R . .
H41C H 0.3832 0.4433 0.4709 0.077 Uiso 1 1 calc R . .
C42 C 0.3495(6) 0.3938(4) 0.6518(4) 0.0642(19) Uani 1 1 d . . .
H42A H 0.2963 0.3753 0.7075 0.096 Uiso 1 1 calc R . .
H42B H 0.3308 0.4584 0.6207 0.096 Uiso 1 1 calc R . .
H42C H 0.4428 0.3867 0.6630 0.096 Uiso 1 1 calc R . .
S2 S 0.79945(15) 0.13342(10) 0.57963(11) 0.0529(5) Uani 1 1 d . . .
O4 O 0.6624(3) 0.1183(3) 0.5615(2) 0.0729(13) Uani 1 1 d . . .
C43 C 0.9013(5) 0.1169(4) 0.4899(4) 0.0592(17) Uani 1 1 d . . .
H43A H 0.8804 0.1641 0.4358 0.089 Uiso 1 1 calc R . .
H43B H 0.8856 0.0555 0.4844 0.089 Uiso 1 1 calc R . .
H43C H 0.9937 0.1220 0.5002 0.089 Uiso 1 1 calc R . .
C44 C 0.8433(6) 0.0323(4) 0.6617(4) 0.071(2) Uani 1 1 d . . .
H44A H 0.7888 0.0274 0.7157 0.106 Uiso 1 1 calc R . .
H44B H 0.9360 0.0354 0.6724 0.106 Uiso 1 1 calc R . .
H44C H 0.8295 -0.0219 0.6422 0.106 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
Cl1 C18 1.721(5) . ?
Cl2 C38 1.723(6) . ?
N7 C23 1.361(6) . ?
N7 C34 1.385(6) . ?
N7 H7D 0.86(4) . ?
O2 C34 1.221(6) . ?
O1 C14 1.218(5) . ?
N5 C23 1.340(5) . ?
N5 N6 1.369(5) . ?
N5 C28 1.427(6) . ?
N1 C3 1.357(5) . ?
N1 N2 1.369(5) . ?
N1 C8 1.456(6) . ?
N3 C14 1.362(6) . ?
N3 C3 1.369(6) . ?
N3 H3 0.83(4) . ?
N6 C21 1.331(6) . ?
N2 C1 1.338(5) . ?
C21 C22 1.406(6) . ?
C21 C24 1.498(6) . ?
C17 C16 1.371(6) . ?
C17 C18 1.383(7) . ?
C17 H17A 0.9500 . ?
C23 C22 1.375(6) . ?
N4 C14 1.379(6) . ?
N4 C15 1.380(6) . ?
N4 H4 0.83(5) . ?
C2 C1 1.393(6) . ?
C2 C3 1.396(6) . ?
C2 H2A 0.9500 . ?
N8 C34 1.379(6) . ?
N8 C35 1.401(6) . ?
N8 H8 0.83(4) . ?
C15 C20 1.394(6) . ?
C15 C16 1.395(6) . ?
C40 C35 1.364(6) . ?
C40 C39 1.391(6) . ?
C40 H40A 0.9500 . ?
C35 C36 1.398(6) . ?
C1 C4 1.498(6) . ?
C24 C27 1.508(6) . ?
C24 C26 1.515(7) . ?
C24 C25 1.521(7) . ?
C16 H16A 0.9500 . ?
C20 C19 1.361(6) . ?
C20 H20A 0.9500 . ?
C18 C19 1.401(7) . ?
C22 H22A 0.9500 . ?
C7 C4 1.527(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C37 C38 1.360(7) . ?
C37 C36 1.390(7) . ?
C37 H37A 0.9500 . ?
C36 H36A 0.9500 . ?
C33 C28 1.369(6) . ?
C33 C32 1.381(7) . ?
C33 H33A 0.9500 . ?
C28 C29 1.402(6) . ?
C4 C6 1.508(7) . ?
C4 C5 1.522(6) . ?
C29 C30 1.374(7) . ?
C29 H29A 0.9500 . ?
C19 H19A 0.9500 . ?
C8 C13 1.357(6) . ?
C8 C9 1.376(7) . ?
C30 C31 1.366(7) . ?
C30 H30A 0.9500 . ?
C32 C31 1.376(7) . ?
C32 H32A 0.9500 . ?
C38 C39 1.396(7) . ?
C10 C11 1.366(7) . ?
C10 C9 1.398(7) . ?
C10 H10A 0.9500 . ?
C13 C12 1.383(7) . ?
C13 H13A 0.9500 . ?
C9 H9A 0.9500 . ?
C39 H39A 0.9500 . ?
C11 C12 1.386(8) . ?
C11 H11A 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C31 H31A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C12 H12A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
S1 O3 1.490(3) . ?
S1 C41 1.756(5) . ?
S1 C42 1.782(5) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
S2 O4 1.489(4) . ?
S2 C44 1.771(6) . ?
S2 C43 1.788(5) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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
C23 N7 C34 124.7(5) . . ?
C23 N7 H7D 121(3) . . ?
C34 N7 H7D 112(3) . . ?
C23 N5 N6 111.7(4) . . ?
C23 N5 C28 130.7(4) . . ?
N6 N5 C28 117.6(4) . . ?
C3 N1 N2 112.9(4) . . ?
C3 N1 C8 130.1(4) . . ?
N2 N1 C8 117.0(4) . . ?
C14 N3 C3 124.4(5) . . ?
C14 N3 H3 115(3) . . ?
C3 N3 H3 120(3) . . ?
C21 N6 N5 104.8(4) . . ?
C1 N2 N1 104.4(4) . . ?
N6 C21 C22 111.1(4) . . ?
N6 C21 C24 119.9(5) . . ?
C22 C21 C24 128.9(5) . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
N5 C23 N7 121.7(5) . . ?
N5 C23 C22 107.4(4) . . ?
N7 C23 C22 130.9(5) . . ?
C14 N4 C15 127.0(5) . . ?
C14 N4 H4 108(4) . . ?
C15 N4 H4 121(4) . . ?
C1 C2 C3 106.3(4) . . ?
C1 C2 H2A 126.9 . . ?
C3 C2 H2A 126.9 . . ?
C34 N8 C35 125.8(5) . . ?
C34 N8 H8 114(3) . . ?
C35 N8 H8 118(3) . . ?
N1 C3 N3 123.0(5) . . ?
N1 C3 C2 105.1(4) . . ?
N3 C3 C2 131.9(5) . . ?
N4 C15 C20 118.5(5) . . ?
N4 C15 C16 123.6(5) . . ?
C20 C15 C16 117.9(5) . . ?
C35 C40 C39 121.2(5) . . ?
C35 C40 H40A 119.4 . . ?
C39 C40 H40A 119.4 . . ?
C40 C35 C36 120.4(5) . . ?
C40 C35 N8 117.7(5) . . ?
C36 C35 N8 121.9(5) . . ?
N2 C1 C2 111.3(4) . . ?
N2 C1 C4 118.7(5) . . ?
C2 C1 C4 130.0(5) . . ?
C21 C24 C27 110.2(4) . . ?
C21 C24 C26 109.6(4) . . ?
C27 C24 C26 109.6(5) . . ?
C21 C24 C25 109.9(4) . . ?
C27 C24 C25 109.0(4) . . ?
C26 C24 C25 108.5(5) . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C19 C20 C15 122.0(5) . . ?
C19 C20 H20A 119.0 . . ?
C15 C20 H20A 119.0 . . ?
C17 C18 C19 119.1(5) . . ?
C17 C18 Cl1 121.2(5) . . ?
C19 C18 Cl1 119.7(5) . . ?
C23 C22 C21 105.0(4) . . ?
C23 C22 H22A 127.5 . . ?
C21 C22 H22A 127.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C38 C37 C36 121.6(6) . . ?
C38 C37 H37A 119.2 . . ?
C36 C37 H37A 119.2 . . ?
C37 C36 C35 118.1(6) . . ?
C37 C36 H36A 121.0 . . ?
C35 C36 H36A 121.0 . . ?
C28 C33 C32 119.3(5) . . ?
C28 C33 H33A 120.3 . . ?
C32 C33 H33A 120.3 . . ?
C33 C28 C29 119.9(5) . . ?
C33 C28 N5 118.9(5) . . ?
C29 C28 N5 121.0(4) . . ?
O2 C34 N8 125.0(5) . . ?
O2 C34 N7 123.1(5) . . ?
N8 C34 N7 111.9(5) . . ?
C1 C4 C6 109.6(4) . . ?
C1 C4 C5 110.2(4) . . ?
C6 C4 C5 108.3(5) . . ?
C1 C4 C7 110.0(4) . . ?
C6 C4 C7 109.7(5) . . ?
C5 C4 C7 109.1(4) . . ?
O1 C14 N3 123.7(5) . . ?
O1 C14 N4 123.8(5) . . ?
N3 C14 N4 112.5(5) . . ?
C30 C29 C28 118.9(5) . . ?
C30 C29 H29A 120.5 . . ?
C28 C29 H29A 120.5 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C13 C8 C9 122.4(5) . . ?
C13 C8 N1 117.9(5) . . ?
C9 C8 N1 119.6(5) . . ?
C31 C30 C29 121.9(5) . . ?
C31 C30 H30A 119.1 . . ?
C29 C30 H30A 119.1 . . ?
C31 C32 C33 121.7(5) . . ?
C31 C32 H32A 119.1 . . ?
C33 C32 H32A 119.1 . . ?
C37 C38 C39 120.2(5) . . ?
C37 C38 Cl2 121.2(5) . . ?
C39 C38 Cl2 118.6(5) . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C8 C13 C12 119.8(6) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 H9A 121.3 . . ?
C10 C9 H9A 121.3 . . ?
C40 C39 C38 118.4(5) . . ?
C40 C39 H39A 120.8 . . ?
C38 C39 H39A 120.8 . . ?
C10 C11 C12 120.0(6) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C30 C31 C32 118.2(6) . . ?
C30 C31 H31A 120.9 . . ?
C32 C31 H31A 120.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 C12 C11 119.3(6) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 S1 C41 105.6(2) . . ?
O3 S1 C42 104.9(3) . . ?
C41 S1 C42 97.3(3) . . ?
S1 C41 H41A 109.5 . . ?
S1 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
S1 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
S1 C42 H42A 109.5 . . ?
S1 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
S1 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O4 S2 C44 105.6(3) . . ?
O4 S2 C43 105.8(2) . . ?
C44 S2 C43 98.7(3) . . ?
S2 C43 H43A 109.5 . . ?
S2 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
S2 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
S2 C44 H44A 109.5 . . ?
S2 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
S2 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N5 N6 C21 1.1(5) . . . . ?
C28 N5 N6 C21 -179.2(4) . . . . ?
C3 N1 N2 C1 -1.1(5) . . . . ?
C8 N1 N2 C1 178.6(4) . . . . ?
N5 N6 C21 C22 -0.5(5) . . . . ?
N5 N6 C21 C24 177.7(4) . . . . ?
N6 N5 C23 N7 177.0(4) . . . . ?
C28 N5 C23 N7 -2.7(8) . . . . ?
N6 N5 C23 C22 -1.2(5) . . . . ?
C28 N5 C23 C22 179.2(4) . . . . ?
C34 N7 C23 N5 165.8(4) . . . . ?
C34 N7 C23 C22 -16.6(8) . . . . ?
N2 N1 C3 N3 -176.4(4) . . . . ?
C8 N1 C3 N3 3.9(8) . . . . ?
N2 N1 C3 C2 1.5(5) . . . . ?
C8 N1 C3 C2 -178.2(4) . . . . ?
C14 N3 C3 N1 -160.8(4) . . . . ?
C14 N3 C3 C2 21.9(8) . . . . ?
C1 C2 C3 N1 -1.2(5) . . . . ?
C1 C2 C3 N3 176.4(5) . . . . ?
C14 N4 C15 C20 -145.3(5) . . . . ?
C14 N4 C15 C16 35.6(8) . . . . ?
C39 C40 C35 C36 3.7(7) . . . . ?
C39 C40 C35 N8 -179.1(4) . . . . ?
C34 N8 C35 C40 146.5(5) . . . . ?
C34 N8 C35 C36 -36.3(7) . . . . ?
N1 N2 C1 C2 0.2(5) . . . . ?
N1 N2 C1 C4 -178.8(4) . . . . ?
C3 C2 C1 N2 0.7(5) . . . . ?
C3 C2 C1 C4 179.5(5) . . . . ?
N6 C21 C24 C27 29.8(6) . . . . ?
C22 C21 C24 C27 -152.3(5) . . . . ?
N6 C21 C24 C26 -90.9(6) . . . . ?
C22 C21 C24 C26 87.0(6) . . . . ?
N6 C21 C24 C25 150.0(5) . . . . ?
C22 C21 C24 C25 -32.2(7) . . . . ?
C18 C17 C16 C15 -0.1(7) . . . . ?
N4 C15 C16 C17 -179.4(4) . . . . ?
C20 C15 C16 C17 1.5(7) . . . . ?
N4 C15 C20 C19 179.2(5) . . . . ?
C16 C15 C20 C19 -1.7(7) . . . . ?
C16 C17 C18 C19 -1.1(7) . . . . ?
C16 C17 C18 Cl1 179.5(4) . . . . ?
N5 C23 C22 C21 0.8(5) . . . . ?
N7 C23 C22 C21 -177.1(5) . . . . ?
N6 C21 C22 C23 -0.1(5) . . . . ?
C24 C21 C22 C23 -178.2(5) . . . . ?
C38 C37 C36 C35 -1.0(8) . . . . ?
C40 C35 C36 C37 -2.7(7) . . . . ?
N8 C35 C36 C37 -179.8(5) . . . . ?
C32 C33 C28 C29 1.4(8) . . . . ?
C32 C33 C28 N5 175.6(4) . . . . ?
C23 N5 C28 C33 142.1(5) . . . . ?
N6 N5 C28 C33 -37.6(6) . . . . ?
C23 N5 C28 C29 -43.8(7) . . . . ?
N6 N5 C28 C29 136.6(5) . . . . ?
C35 N8 C34 O2 9.6(8) . . . . ?
C35 N8 C34 N7 -173.0(4) . . . . ?
C23 N7 C34 O2 -6.9(8) . . . . ?
C23 N7 C34 N8 175.7(4) . . . . ?
N2 C1 C4 C6 75.3(6) . . . . ?
C2 C1 C4 C6 -103.5(6) . . . . ?
N2 C1 C4 C5 -165.6(4) . . . . ?
C2 C1 C4 C5 15.6(7) . . . . ?
N2 C1 C4 C7 -45.3(6) . . . . ?
C2 C1 C4 C7 135.9(5) . . . . ?
C3 N3 C14 O1 2.1(8) . . . . ?
C3 N3 C14 N4 -179.4(4) . . . . ?
C15 N4 C14 O1 -10.9(8) . . . . ?
C15 N4 C14 N3 170.5(5) . . . . ?
C33 C28 C29 C30 -2.5(8) . . . . ?
N5 C28 C29 C30 -176.6(5) . . . . ?
C15 C20 C19 C18 0.4(7) . . . . ?
C17 C18 C19 C20 1.0(7) . . . . ?
Cl1 C18 C19 C20 -179.6(4) . . . . ?
C3 N1 C8 C13 -148.1(5) . . . . ?
N2 N1 C8 C13 32.3(6) . . . . ?
C3 N1 C8 C9 36.4(7) . . . . ?
N2 N1 C8 C9 -143.3(5) . . . . ?
C28 C29 C30 C31 2.6(8) . . . . ?
C28 C33 C32 C31 -0.2(8) . . . . ?
C36 C37 C38 C39 3.8(8) . . . . ?
C36 C37 C38 Cl2 -177.2(4) . . . . ?
C9 C8 C13 C12 -0.8(8) . . . . ?
N1 C8 C13 C12 -176.2(5) . . . . ?
C13 C8 C9 C10 1.3(8) . . . . ?
N1 C8 C9 C10 176.6(4) . . . . ?
C11 C10 C9 C8 -2.1(8) . . . . ?
C35 C40 C39 C38 -0.9(7) . . . . ?
C37 C38 C39 C40 -2.8(8) . . . . ?
Cl2 C38 C39 C40 178.1(4) . . . . ?
C9 C10 C11 C12 2.6(9) . . . . ?
C29 C30 C31 C32 -1.5(9) . . . . ?
C33 C32 C31 C30 0.3(8) . . . . ?
C8 C13 C12 C11 1.2(9) . . . . ?
C10 C11 C12 C13 -2.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.75
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.085

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' test in P-1'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            259.78
_reflns_d_resolution_high        0.7896
####################################################################### 
# 
# 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_compound-4
_database_code_depnum_ccdc_archive 'CCDC 1474056'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Cl N4 O, C2 H6 S O'
_chemical_formula_sum            'C23 H29 Cl N4 O2 S'
_chemical_formula_weight         461.01

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5365(19)
_cell_length_b                   10.4435(13)
_cell_length_c                   13.1768(16)
_cell_angle_alpha                85.347(9)
_cell_angle_beta                 84.622(10)
_cell_angle_gamma                68.226(17)
_cell_volume                     1211.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    164(2)
_cell_measurement_reflns_used    156
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         250
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            15634
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5625
_reflns_number_gt                4529
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.05P)²+0.2P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5625
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65461(4) 0.71924(4) 0.15049(3) 0.02927(10) Uani 1 1 d . . .
Cl1 Cl 1.16085(6) 0.09848(6) -0.31513(3) 0.05657(15) Uani 1 1 d . . .
O1 O 0.61516(11) 0.17124(10) 0.07966(8) 0.0306(2) Uani 1 1 d . . .
N3 N 0.53868(14) 0.37319(13) 0.16229(9) 0.0284(3) Uani 1 1 d . . .
O2 O 0.62567(14) 0.60729(11) 0.10048(9) 0.0443(3) Uani 1 1 d . . .
N2 N 0.35302(13) 0.43878(11) 0.30236(9) 0.0246(2) Uani 1 1 d . . .
N1 N 0.22580(13) 0.41613(12) 0.34514(9) 0.0254(2) Uani 1 1 d . . .
C15 C 0.62274(15) 0.28382(14) 0.08855(10) 0.0248(3) Uani 1 1 d . . .
N4 N 0.71604(14) 0.33725(13) 0.02861(9) 0.0280(3) Uani 1 1 d . . .
C8 C 0.39599(15) 0.53796(14) 0.34649(10) 0.0235(3) Uani 1 1 d . . .
C9 C 0.28232(16) 0.65526(14) 0.38382(10) 0.0255(3) Uani 1 1 d . . .
H9A H 0.1791 0.6715 0.3755 0.031 Uiso 1 1 calc R . .
C21 C 0.87249(16) 0.36119(15) -0.11894(11) 0.0298(3) Uani 1 1 d . . .
H21A H 0.8370 0.4574 -0.1088 0.036 Uiso 1 1 calc R . .
C3 C 0.21677(15) 0.31700(13) 0.29214(10) 0.0239(3) Uani 1 1 d . . .
C1 C 0.41841(15) 0.35629(13) 0.22226(10) 0.0239(3) Uani 1 1 d . . .
C12 C 0.58300(17) 0.60948(15) 0.40771(11) 0.0289(3) Uani 1 1 d . . .
H12A H 0.6863 0.5939 0.4150 0.035 Uiso 1 1 calc R . .
C2 C 0.33535(16) 0.27466(14) 0.21506(11) 0.0262(3) Uani 1 1 d . . .
H2A H 0.3538 0.2047 0.1682 0.031 Uiso 1 1 calc R . .
C4 C 0.08758(16) 0.26563(14) 0.31597(11) 0.0276(3) Uani 1 1 d . . .
C13 C 0.54664(16) 0.51403(15) 0.35883(10) 0.0273(3) Uani 1 1 d . . .
H13A H 0.6242 0.4332 0.3341 0.033 Uiso 1 1 calc R . .
C16 C 0.81886(15) 0.27526(14) -0.05226(10) 0.0243(3) Uani 1 1 d . . .
C11 C 0.47097(17) 0.72770(14) 0.44626(11) 0.0289(3) Uani 1 1 d . . .
C17 C 0.87286(16) 0.13461(15) -0.06807(11) 0.0292(3) Uani 1 1 d . . .
H17A H 0.8378 0.0751 -0.0234 0.035 Uiso 1 1 calc R . .
C10 C 0.32093(17) 0.74830(14) 0.43333(10) 0.0277(3) Uani 1 1 d . . .
H10A H 0.2430 0.8282 0.4591 0.033 Uiso 1 1 calc R . .
C19 C 1.02839(17) 0.16725(17) -0.21383(11) 0.0336(3) Uani 1 1 d . . .
C18 C 0.97782(17) 0.08061(16) -0.14894(12) 0.0338(3) Uani 1 1 d . . .
H18A H 1.0145 -0.0155 -0.1595 0.041 Uiso 1 1 calc R . .
C23 C 0.47230(18) 0.84457(16) 0.18198(13) 0.0383(4) Uani 1 1 d . . .
H23A H 0.4161 0.8750 0.1204 0.057 Uiso 1 1 calc R . .
H23B H 0.4835 0.9239 0.2102 0.057 Uiso 1 1 calc R . .
H23C H 0.4170 0.8037 0.2326 0.057 Uiso 1 1 calc R . .
C14 C 0.5111(2) 0.83017(16) 0.49936(14) 0.0417(4) Uani 1 1 d . . .
H14A H 0.4899 0.9153 0.4563 0.062 Uiso 1 1 calc R . .
H14B H 0.6189 0.7914 0.5119 0.062 Uiso 1 1 calc R . .
H14C H 0.4506 0.8507 0.5645 0.062 Uiso 1 1 calc R . .
C20 C 0.97689(17) 0.30688(16) -0.19965(11) 0.0338(3) Uani 1 1 d . . .
H20A H 1.0126 0.3655 -0.2448 0.041 Uiso 1 1 calc R . .
C22 C 0.7079(2) 0.81973(17) 0.04895(12) 0.0388(4) Uani 1 1 d . . .
H22A H 0.8082 0.7655 0.0184 0.058 Uiso 1 1 calc R . .
H22B H 0.7109 0.9035 0.0758 0.058 Uiso 1 1 calc R . .
H22C H 0.6339 0.8454 -0.0031 0.058 Uiso 1 1 calc R . .
C6 C 0.1511(2) 0.10936(17) 0.33757(17) 0.0503(5) Uani 1 1 d . . .
H6A H 0.2133 0.0645 0.2777 0.075 Uiso 1 1 calc R . .
H6B H 0.0673 0.0762 0.3526 0.075 Uiso 1 1 calc R . .
H6C H 0.2133 0.0871 0.3963 0.075 Uiso 1 1 calc R . .
C7 C -0.0111(2) 0.3353(2) 0.40857(15) 0.0525(5) Uani 1 1 d . . .
H7A H 0.0499 0.3131 0.4680 0.079 Uiso 1 1 calc R . .
H7B H -0.0949 0.3021 0.4225 0.079 Uiso 1 1 calc R . .
H7C H -0.0516 0.4356 0.3947 0.079 Uiso 1 1 calc R . .
C5 C -0.0100(2) 0.2997(2) 0.22424(14) 0.0476(4) Uani 1 1 d . . .
H5A H 0.0521 0.2545 0.1644 0.071 Uiso 1 1 calc R . .
H5B H -0.0508 0.3998 0.2100 0.071 Uiso 1 1 calc R . .
H5C H -0.0936 0.2665 0.2396 0.071 Uiso 1 1 calc R . .
H4A H 0.7054(19) 0.4166(19) 0.0406(13) 0.034(5) Uiso 1 1 d . . .
H3A H 0.5480(19) 0.4480(18) 0.1615(13) 0.033(5) Uiso 1 1 d . . .


_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 1.5087(12) . ?
S1 C23 1.7812(16) . ?
S1 C22 1.7863(15) . ?
Cl1 C19 1.7492(15) . ?
O1 C15 1.2200(16) . ?
N3 C15 1.3798(18) . ?
N3 C1 1.3888(18) . ?
N3 H3A 0.817(17) . ?
N2 C1 1.3676(17) . ?
N2 N1 1.3816(15) . ?
N2 C8 1.4270(17) . ?
N1 C3 1.3272(17) . ?
C15 N4 1.3755(18) . ?
N4 C16 1.4003(18) . ?
N4 H4A 0.823(18) . ?
C8 C13 1.387(2) . ?
C8 C9 1.3893(19) . ?
C9 C10 1.3852(19) . ?
C9 H9A 0.9500 . ?
C21 C20 1.387(2) . ?
C21 C16 1.4027(19) . ?
C21 H21A 0.9500 . ?
C3 C2 1.4116(19) . ?
C3 C4 1.5148(19) . ?
C1 C2 1.3752(19) . ?
C12 C13 1.390(2) . ?
C12 C11 1.395(2) . ?
C12 H12A 0.9500 . ?
C2 H2A 0.9500 . ?
C4 C7 1.525(2) . ?
C4 C6 1.528(2) . ?
C4 C5 1.533(2) . ?
C13 H13A 0.9500 . ?
C16 C17 1.391(2) . ?
C11 C10 1.391(2) . ?
C11 C14 1.502(2) . ?
C17 C18 1.391(2) . ?
C17 H17A 0.9500 . ?
C10 H10A 0.9500 . ?
C19 C20 1.378(2) . ?
C19 C18 1.380(2) . ?
C18 H18A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 H20A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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 C23 105.46(8) . . ?
O2 S1 C22 105.93(7) . . ?
C23 S1 C22 96.58(8) . . ?
C15 N3 C1 123.58(12) . . ?
C15 N3 H3A 117.3(12) . . ?
C1 N3 H3A 117.7(12) . . ?
C1 N2 N1 111.12(11) . . ?
C1 N2 C8 130.90(11) . . ?
N1 N2 C8 117.97(11) . . ?
C3 N1 N2 104.85(11) . . ?
O1 C15 N4 125.11(13) . . ?
O1 C15 N3 123.46(13) . . ?
N4 C15 N3 111.42(12) . . ?
C15 N4 C16 127.55(12) . . ?
C15 N4 H4A 114.7(12) . . ?
C16 N4 H4A 117.6(12) . . ?
C13 C8 C9 120.38(13) . . ?
C13 C8 N2 121.19(12) . . ?
C9 C8 N2 118.28(12) . . ?
C10 C9 C8 119.33(13) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C20 C21 C16 120.53(14) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?
N1 C3 C2 111.74(12) . . ?
N1 C3 C4 120.30(12) . . ?
C2 C3 C4 127.93(13) . . ?
N2 C1 C2 106.97(12) . . ?
N2 C1 N3 120.08(12) . . ?
C2 C1 N3 132.76(13) . . ?
C13 C12 C11 121.36(14) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C1 C2 C3 105.26(12) . . ?
C1 C2 H2A 127.4 . . ?
C3 C2 H2A 127.4 . . ?
C3 C4 C7 110.35(12) . . ?
C3 C4 C6 109.58(12) . . ?
C7 C4 C6 109.50(15) . . ?
C3 C4 C5 109.44(12) . . ?
C7 C4 C5 108.77(14) . . ?
C6 C4 C5 109.18(14) . . ?
C8 C13 C12 119.36(13) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C17 C16 N4 123.93(12) . . ?
C17 C16 C21 118.86(13) . . ?
N4 C16 C21 117.18(12) . . ?
C10 C11 C12 117.91(13) . . ?
C10 C11 C14 121.01(14) . . ?
C12 C11 C14 121.08(14) . . ?
C18 C17 C16 120.38(13) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C9 C10 C11 121.65(13) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C20 C19 C18 121.01(14) . . ?
C20 C19 Cl1 119.54(12) . . ?
C18 C19 Cl1 119.45(12) . . ?
C19 C18 C17 119.72(14) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C20 C21 119.49(14) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N1 C3 1.54(14) . . . . ?
C8 N2 N1 C3 -177.69(11) . . . . ?
C1 N3 C15 O1 -11.7(2) . . . . ?
C1 N3 C15 N4 169.15(13) . . . . ?
O1 C15 N4 C16 -0.3(2) . . . . ?
N3 C15 N4 C16 178.85(13) . . . . ?
C1 N2 C8 C13 -39.7(2) . . . . ?
N1 N2 C8 C13 139.30(13) . . . . ?
C1 N2 C8 C9 144.87(14) . . . . ?
N1 N2 C8 C9 -36.09(17) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
N2 C8 C9 C10 175.56(11) . . . . ?
N2 N1 C3 C2 -0.28(14) . . . . ?
N2 N1 C3 C4 -178.77(11) . . . . ?
N1 N2 C1 C2 -2.20(15) . . . . ?
C8 N2 C1 C2 176.89(13) . . . . ?
N1 N2 C1 N3 173.41(12) . . . . ?
C8 N2 C1 N3 -7.5(2) . . . . ?
C15 N3 C1 N2 171.63(12) . . . . ?
C15 N3 C1 C2 -14.1(2) . . . . ?
N2 C1 C2 C3 1.89(15) . . . . ?
N3 C1 C2 C3 -172.93(14) . . . . ?
N1 C3 C2 C1 -1.02(15) . . . . ?
C4 C3 C2 C1 177.32(13) . . . . ?
N1 C3 C4 C7 -4.18(19) . . . . ?
C2 C3 C4 C7 177.60(15) . . . . ?
N1 C3 C4 C6 -124.83(15) . . . . ?
C2 C3 C4 C6 57.0(2) . . . . ?
N1 C3 C4 C5 115.48(15) . . . . ?
C2 C3 C4 C5 -62.74(19) . . . . ?
C9 C8 C13 C12 -0.9(2) . . . . ?
N2 C8 C13 C12 -176.15(12) . . . . ?
C11 C12 C13 C8 1.2(2) . . . . ?
C15 N4 C16 C17 -18.0(2) . . . . ?
C15 N4 C16 C21 163.76(14) . . . . ?
C20 C21 C16 C17 0.4(2) . . . . ?
C20 C21 C16 N4 178.71(13) . . . . ?
C13 C12 C11 C10 -0.7(2) . . . . ?
C13 C12 C11 C14 179.77(13) . . . . ?
N4 C16 C17 C18 -178.42(13) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C12 C11 C10 C9 -0.1(2) . . . . ?
C14 C11 C10 C9 179.48(13) . . . . ?
C20 C19 C18 C17 0.2(2) . . . . ?
Cl1 C19 C18 C17 179.80(12) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
Cl1 C19 C20 C21 -179.63(11) . . . . ?
C16 C21 C20 C19 -0.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.044

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' nm in P-1'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            170.53
_reflns_d_resolution_high        0.7570
####################################################################### 
# 
# 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_compound-5-MeOH
_database_code_depnum_ccdc_archive 'CCDC 1474057'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Cl N4 O, 2(C H4 O)'
_chemical_formula_sum            'C23 H31 Cl N4 O3'
_chemical_formula_weight         446.97

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2698(16)
_cell_length_b                   14.906(2)
_cell_length_c                   16.249(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.954(9)
_cell_angle_gamma                90.00
_cell_volume                     2469.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    174
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         382
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            36111
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         28.25
_reflns_number_total             5966
_reflns_number_gt                4387
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.04P)²+1.5P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5966
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.66363(6) 0.15719(4) 0.14910(4) 0.05236(17) Uani 1 1 d . . .
O1 O 0.43327(12) 0.57236(8) 0.11023(9) 0.0354(3) Uani 1 1 d . . .
N3 N 0.21884(15) 0.60488(10) 0.12150(10) 0.0287(3) Uani 1 1 d . . .
N4 N 0.28525(15) 0.45858(10) 0.11840(10) 0.0307(3) Uani 1 1 d . . .
C1 C 0.29087(17) 0.84049(11) 0.12451(10) 0.0263(3) Uani 1 1 d . . .
C3 C 0.23421(16) 0.69737(11) 0.12392(10) 0.0258(3) Uani 1 1 d . . .
N2 N 0.16338(15) 0.83987(10) 0.13144(10) 0.0324(3) Uani 1 1 d . . .
C2 C 0.34004(16) 0.75305(11) 0.11922(11) 0.0273(4) Uani 1 1 d . . .
H2A H 0.4276 0.7360 0.1136 0.033 Uiso 1 1 calc R . .
C15 C 0.32266(17) 0.54687(11) 0.11628(10) 0.0272(4) Uani 1 1 d . . .
C16 C 0.37523(17) 0.38645(11) 0.12275(11) 0.0273(4) Uani 1 1 d . . .
N1 N 0.12943(14) 0.75044(10) 0.13144(10) 0.0305(3) Uani 1 1 d . . .
C4 C 0.36539(17) 0.92831(12) 0.12615(11) 0.0302(4) Uani 1 1 d . . .
O2 O 0.01714(14) 0.47052(11) 0.14419(11) 0.0455(4) Uani 1 1 d . . .
O3 O 0.00870(16) 0.96520(12) 0.19570(10) 0.0535(4) Uani 1 1 d . . .
C18 C 0.56743(18) 0.31394(12) 0.08326(12) 0.0334(4) Uani 1 1 d . . .
H18A H 0.6394 0.3131 0.0516 0.040 Uiso 1 1 calc R . .
C8 C -0.00421(17) 0.72457(12) 0.13364(13) 0.0338(4) Uani 1 1 d . . .
C20 C 0.44381(19) 0.24315(12) 0.18210(12) 0.0363(4) Uani 1 1 d . . .
H20A H 0.4313 0.1941 0.2176 0.044 Uiso 1 1 calc R . .
C17 C 0.47936(18) 0.38462(12) 0.07592(11) 0.0317(4) Uani 1 1 d . . .
H17A H 0.4904 0.4322 0.0385 0.038 Uiso 1 1 calc R . .
C19 C 0.54944(19) 0.24461(12) 0.13709(12) 0.0354(4) Uani 1 1 d . . .
C21 C 0.35638(18) 0.31422(12) 0.17471(12) 0.0330(4) Uani 1 1 d . . .
H21A H 0.2831 0.3138 0.2052 0.040 Uiso 1 1 calc R . .
C6 C 0.3781(2) 0.96540(13) 0.21488(12) 0.0402(5) Uani 1 1 d . . .
H6A H 0.4210 0.9207 0.2533 0.060 Uiso 1 1 calc R . .
H6B H 0.2907 0.9788 0.2301 0.060 Uiso 1 1 calc R . .
H6C H 0.4307 1.0204 0.2180 0.060 Uiso 1 1 calc R . .
C9 C -0.0384(2) 0.68621(14) 0.20595(15) 0.0425(5) Uani 1 1 d . . .
H9A H 0.0256 0.6789 0.2528 0.051 Uiso 1 1 calc R . .
C7 C 0.2912(2) 0.99568(14) 0.06662(14) 0.0449(5) Uani 1 1 d . . .
H7A H 0.2835 0.9719 0.0100 0.067 Uiso 1 1 calc R . .
H7B H 0.3392 1.0526 0.0690 0.067 Uiso 1 1 calc R . .
H7C H 0.2034 1.0056 0.0828 0.067 Uiso 1 1 calc R . .
C13 C -0.09503(19) 0.73799(14) 0.06394(14) 0.0427(5) Uani 1 1 d . . .
C5 C 0.5020(2) 0.91247(14) 0.10056(15) 0.0438(5) Uani 1 1 d . . .
H5A H 0.4937 0.8875 0.0444 0.066 Uiso 1 1 calc R . .
H5B H 0.5502 0.8703 0.1392 0.066 Uiso 1 1 calc R . .
H5C H 0.5496 0.9695 0.1016 0.066 Uiso 1 1 calc R . .
C12 C -0.2242(2) 0.71101(17) 0.07054(18) 0.0578(7) Uani 1 1 d . . .
H12A H -0.2898 0.7205 0.0249 0.069 Uiso 1 1 calc R . .
C10 C -0.1666(2) 0.65863(15) 0.20921(18) 0.0547(6) Uani 1 1 d . . .
H10A H -0.1906 0.6313 0.2580 0.066 Uiso 1 1 calc R . .
C11 C -0.2586(2) 0.67090(16) 0.1418(2) 0.0602(7) Uani 1 1 d . . .
H11A H -0.3464 0.6518 0.1438 0.072 Uiso 1 1 calc R . .
C14 C -0.0576(3) 0.77901(19) -0.01395(15) 0.0622(7) Uani 1 1 d . . .
H14A H -0.0528 0.8444 -0.0077 0.093 Uiso 1 1 calc R . .
H14B H -0.1235 0.7636 -0.0605 0.093 Uiso 1 1 calc R . .
H14C H 0.0281 0.7559 -0.0246 0.093 Uiso 1 1 calc R . .
C22 C -0.0992(3) 0.4482(2) 0.09238(18) 0.0702(8) Uani 1 1 d . . .
H22A H -0.1374 0.3937 0.1133 0.105 Uiso 1 1 calc R . .
H22B H -0.0786 0.4376 0.0358 0.105 Uiso 1 1 calc R . .
H22C H -0.1620 0.4976 0.0921 0.105 Uiso 1 1 calc R . .
C23 C -0.1130(3) 0.9689(3) 0.1492(2) 0.1159(17) Uani 1 1 d . . .
H23A H -0.1723 1.0056 0.1782 0.174 Uiso 1 1 calc R . .
H23B H -0.1487 0.9081 0.1415 0.174 Uiso 1 1 calc R . .
H23C H -0.1044 0.9956 0.0950 0.174 Uiso 1 1 calc R . .
H3B H 0.144(2) 0.5825(13) 0.1245(12) 0.030(5) Uiso 1 1 d . . .
H4A H 0.204(2) 0.4478(14) 0.1270(12) 0.034(5) Uiso 1 1 d . . .
H3A H 0.050(3) 0.924(2) 0.1792(19) 0.077(9) Uiso 1 1 d . . .
H2B H 0.007(2) 0.4669(18) 0.1937(17) 0.055(8) Uiso 1 1 d . . .


_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
Cl1 C19 1.7481(19) . ?
O1 C15 1.213(2) . ?
N3 C15 1.383(2) . ?
N3 C3 1.388(2) . ?
N3 H3B 0.85(2) . ?
N4 C15 1.373(2) . ?
N4 C16 1.414(2) . ?
N4 H4A 0.87(2) . ?
C1 N2 1.328(2) . ?
C1 C2 1.404(2) . ?
C1 C4 1.515(2) . ?
C3 N1 1.353(2) . ?
C3 C2 1.377(2) . ?
N2 N1 1.378(2) . ?
C2 H2A 0.9500 . ?
C16 C17 1.386(2) . ?
C16 C21 1.396(2) . ?
N1 C8 1.430(2) . ?
C4 C5 1.529(3) . ?
C4 C7 1.532(3) . ?
C4 C6 1.535(3) . ?
O2 C22 1.415(3) . ?
O2 H2B 0.83(3) . ?
O3 C23 1.381(3) . ?
O3 H3A 0.82(3) . ?
C18 C19 1.381(3) . ?
C18 C17 1.384(3) . ?
C18 H18A 0.9500 . ?
C8 C9 1.390(3) . ?
C8 C13 1.392(3) . ?
C20 C19 1.380(3) . ?
C20 C21 1.384(3) . ?
C20 H20A 0.9500 . ?
C17 H17A 0.9500 . ?
C21 H21A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 C12 1.402(3) . ?
C13 C14 1.497(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C12 C11 1.386(4) . ?
C12 H12A 0.9500 . ?
C10 C11 1.370(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C15 N3 C3 122.47(15) . . ?
C15 N3 H3B 118.2(14) . . ?
C3 N3 H3B 119.3(14) . . ?
C15 N4 C16 123.17(15) . . ?
C15 N4 H4A 117.0(14) . . ?
C16 N4 H4A 118.7(14) . . ?
N2 C1 C2 111.37(15) . . ?
N2 C1 C4 120.38(15) . . ?
C2 C1 C4 128.21(15) . . ?
N1 C3 C2 107.12(15) . . ?
N1 C3 N3 119.63(15) . . ?
C2 C3 N3 133.24(16) . . ?
C1 N2 N1 105.00(14) . . ?
C3 C2 C1 105.31(15) . . ?
C3 C2 H2A 127.3 . . ?
C1 C2 H2A 127.3 . . ?
O1 C15 N4 124.76(16) . . ?
O1 C15 N3 123.05(16) . . ?
N4 C15 N3 112.19(15) . . ?
C17 C16 C21 119.32(16) . . ?
C17 C16 N4 122.04(16) . . ?
C21 C16 N4 118.63(16) . . ?
C3 N1 N2 111.20(14) . . ?
C3 N1 C8 128.37(15) . . ?
N2 N1 C8 120.29(14) . . ?
C1 C4 C5 109.87(15) . . ?
C1 C4 C7 110.12(15) . . ?
C5 C4 C7 109.40(16) . . ?
C1 C4 C6 108.24(15) . . ?
C5 C4 C6 109.55(16) . . ?
C7 C4 C6 109.65(16) . . ?
C22 O2 H2B 111.4(18) . . ?
C23 O3 H3A 109(2) . . ?
C19 C18 C17 119.22(17) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C9 C8 C13 122.29(18) . . ?
C9 C8 N1 118.26(18) . . ?
C13 C8 N1 119.44(18) . . ?
C19 C20 C21 119.03(17) . . ?
C19 C20 H20A 120.5 . . ?
C21 C20 H20A 120.5 . . ?
C18 C17 C16 120.48(17) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C20 C19 C18 121.44(17) . . ?
C20 C19 Cl1 119.27(15) . . ?
C18 C19 Cl1 119.29(15) . . ?
C20 C21 C16 120.43(17) . . ?
C20 C21 H21A 119.8 . . ?
C16 C21 H21A 119.8 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C13 C12 116.3(2) . . ?
C8 C13 C14 122.08(19) . . ?
C12 C13 C14 121.6(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N3 C3 N1 -178.11(16) . . . . ?
C15 N3 C3 C2 2.7(3) . . . . ?
C2 C1 N2 N1 0.6(2) . . . . ?
C4 C1 N2 N1 -177.30(15) . . . . ?
N1 C3 C2 C1 0.07(19) . . . . ?
N3 C3 C2 C1 179.30(18) . . . . ?
N2 C1 C2 C3 -0.4(2) . . . . ?
C4 C1 C2 C3 177.24(16) . . . . ?
C16 N4 C15 O1 7.1(3) . . . . ?
C16 N4 C15 N3 -173.18(16) . . . . ?
C3 N3 C15 O1 -2.9(3) . . . . ?
C3 N3 C15 N4 177.35(16) . . . . ?
C15 N4 C16 C17 -42.6(3) . . . . ?
C15 N4 C16 C21 138.72(18) . . . . ?
C2 C3 N1 N2 0.3(2) . . . . ?
N3 C3 N1 N2 -179.08(15) . . . . ?
C2 C3 N1 C8 176.01(17) . . . . ?
N3 C3 N1 C8 -3.3(3) . . . . ?
C1 N2 N1 C3 -0.5(2) . . . . ?
C1 N2 N1 C8 -176.65(16) . . . . ?
N2 C1 C4 C5 -169.13(16) . . . . ?
C2 C1 C4 C5 13.4(3) . . . . ?
N2 C1 C4 C7 -48.6(2) . . . . ?
C2 C1 C4 C7 133.97(19) . . . . ?
N2 C1 C4 C6 71.3(2) . . . . ?
C2 C1 C4 C6 -106.2(2) . . . . ?
C3 N1 C8 C9 75.5(2) . . . . ?
N2 N1 C8 C9 -109.1(2) . . . . ?
C3 N1 C8 C13 -104.2(2) . . . . ?
N2 N1 C8 C13 71.2(2) . . . . ?
C19 C18 C17 C16 0.8(3) . . . . ?
C21 C16 C17 C18 -2.9(3) . . . . ?
N4 C16 C17 C18 178.41(17) . . . . ?
C21 C20 C19 C18 -1.9(3) . . . . ?
C21 C20 C19 Cl1 177.58(15) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C17 C18 C19 Cl1 -177.83(14) . . . . ?
C19 C20 C21 C16 -0.3(3) . . . . ?
C17 C16 C21 C20 2.7(3) . . . . ?
N4 C16 C21 C20 -178.62(17) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
N1 C8 C9 C10 -178.55(17) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
N1 C8 C13 C12 179.97(17) . . . . ?
C9 C8 C13 C14 -179.7(2) . . . . ?
N1 C8 C13 C14 -0.1(3) . . . . ?
C8 C13 C12 C11 -1.7(3) . . . . ?
C14 C13 C12 C11 178.3(2) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C13 C12 C11 C10 1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.051

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' nm in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            351.74
_reflns_d_resolution_high        0.7509
####################################################################### 
# 
# 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_compound-5DMSO
_database_code_depnum_ccdc_archive 'CCDC 1474058'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Cl N4 O, C2 H6 O S'
_chemical_formula_sum            'C23 H29 Cl N4 O2 S'
_chemical_formula_weight         461.01

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.753(3)
_cell_length_b                   16.394(4)
_cell_length_c                   9.6378(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.355(7)
_cell_angle_gamma                90.00
_cell_volume                     2420.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    158(2)
_cell_measurement_reflns_used    171
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      158(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         260
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            19571
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         29.50
_reflns_number_total             6483
_reflns_number_gt                5076
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.05P)²+1.3P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_number_reflns         6483
_refine_ls_number_parameters     292
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69090(4) 0.79630(5) 0.80391(7) 0.03725(17) Uani 1 1 d . . .
Cl1 Cl 0.45126(5) 0.96970(5) -0.15155(9) 0.0480(2) Uani 1 1 d . . .
N4 N 0.75240(14) 0.88141(15) 0.4853(3) 0.0314(5) Uani 1 1 d D . .
H4A H 0.738(2) 0.8595(18) 0.542(3) 0.038 Uiso 1 1 d D . .
O1 O 0.86836(13) 0.91534(13) 0.4559(2) 0.0388(5) Uani 1 1 d . . .
C19 C 0.54091(16) 0.94314(17) 0.0356(3) 0.0323(6) Uani 1 1 d . . .
N1 N 1.02763(14) 0.85215(15) 0.9364(2) 0.0338(5) Uani 1 1 d . . .
C3 C 0.98114(16) 0.86565(15) 0.7747(3) 0.0274(5) Uani 1 1 d . . .
N2 N 1.11597(14) 0.85727(15) 0.9951(3) 0.0351(5) Uani 1 1 d . . .
C17 C 0.68705(17) 0.96978(15) 0.2456(3) 0.0294(5) Uani 1 1 d . . .
H17A H 0.7389 1.0015 0.2881 0.035 Uiso 1 1 calc R . .
C2 C 1.04057(16) 0.88024(16) 0.7261(3) 0.0274(5) Uani 1 1 d . . .
H2A H 1.0288 0.8917 0.6203 0.033 Uiso 1 1 calc R . .
C15 C 0.83916(16) 0.88996(18) 0.5377(3) 0.0296(5) Uani 1 1 d . . .
O2 O 0.75891(13) 0.82291(13) 0.7647(2) 0.0388(5) Uani 1 1 d . . .
N3 N 0.89085(14) 0.86433(14) 0.6948(2) 0.0317(5) Uani 1 1 d D . .
H3A H 0.8687(19) 0.8506(19) 0.753(3) 0.038 Uiso 1 1 d D . .
C23 C 0.7181(2) 0.69485(18) 0.8792(4) 0.0421(7) Uani 1 1 d . . .
H23A H 0.7125 0.6585 0.7937 0.063 Uiso 1 1 calc R . .
H23B H 0.6784 0.6767 0.9157 0.063 Uiso 1 1 calc R . .
H23C H 0.7783 0.6934 0.9695 0.063 Uiso 1 1 calc R . .
C12 C 0.95513(18) 0.74958(19) 1.1913(3) 0.0371(6) Uani 1 1 d . . .
H12A H 0.9417 0.6965 1.2123 0.045 Uiso 1 1 calc R . .
C8 C 0.99702(15) 0.83849(18) 1.0470(3) 0.0305(6) Uani 1 1 d . . .
C18 C 0.61524(18) 0.99039(16) 0.0984(3) 0.0316(5) Uani 1 1 d . . .
H18A H 0.6173 1.0368 0.0413 0.038 Uiso 1 1 calc R . .
C20 C 0.53634(17) 0.87606(17) 0.1164(3) 0.0341(6) Uani 1 1 d . . .
H20A H 0.4848 0.8439 0.0712 0.041 Uiso 1 1 calc R . .
C1 C 1.12288(16) 0.87453(15) 0.8674(3) 0.0270(5) Uani 1 1 d . . .
C21 C 0.60746(17) 0.85568(17) 0.2642(3) 0.0324(6) Uani 1 1 d . . .
H21A H 0.6046 0.8093 0.3205 0.039 Uiso 1 1 calc R . .
C16 C 0.68362(16) 0.90286(15) 0.3314(3) 0.0260(5) Uani 1 1 d . . .
C14 C 0.9728(2) 0.68983(18) 0.9696(4) 0.0421(7) Uani 1 1 d . . .
H14A H 0.9685 0.6389 1.0184 0.063 Uiso 1 1 calc R . .
H14B H 1.0263 0.6894 0.9639 0.063 Uiso 1 1 calc R . .
H14C H 0.9221 0.6949 0.8610 0.063 Uiso 1 1 calc R . .
C4 C 1.21156(16) 0.89019(16) 0.8857(3) 0.0294(5) Uani 1 1 d . . .
C13 C 0.97489(16) 0.75991(17) 1.0690(3) 0.0314(6) Uani 1 1 d . . .
C11 C 0.9546(2) 0.81385(19) 1.2814(4) 0.0426(7) Uani 1 1 d . . .
H11A H 0.9417 0.8047 1.3645 0.051 Uiso 1 1 calc R . .
C9 C 0.99451(19) 0.90535(18) 1.1349(3) 0.0358(6) Uani 1 1 d . . .
H9A H 1.0074 0.9587 1.1145 0.043 Uiso 1 1 calc R . .
C7 C 1.2853(2) 0.8655(3) 1.0552(4) 0.0597(10) Uani 1 1 d . . .
H7A H 1.2791 0.8960 1.1363 0.090 Uiso 1 1 calc R . .
H7B H 1.3420 0.8780 1.0659 0.090 Uiso 1 1 calc R . .
H7C H 1.2816 0.8069 1.0710 0.090 Uiso 1 1 calc R . .
C10 C 0.9727(2) 0.8918(2) 1.2529(4) 0.0450(7) Uani 1 1 d . . .
H10A H 0.9703 0.9362 1.3137 0.054 Uiso 1 1 calc R . .
C6 C 1.2205(2) 0.9805(2) 0.8659(6) 0.0702(12) Uani 1 1 d . . .
H6A H 1.1839 0.9955 0.7524 0.105 Uiso 1 1 calc R . .
H6B H 1.2816 0.9934 0.9021 0.105 Uiso 1 1 calc R . .
H6C H 1.2017 1.0113 0.9303 0.105 Uiso 1 1 calc R . .
C5 C 1.2221(3) 0.8411(3) 0.7630(5) 0.0738(13) Uani 1 1 d . . .
H5A H 1.1781 0.8585 0.6544 0.111 Uiso 1 1 calc R . .
H5B H 1.2145 0.7830 0.7763 0.111 Uiso 1 1 calc R . .
H5C H 1.2806 0.8503 0.7791 0.111 Uiso 1 1 calc R . .
C22 C 0.7190(3) 0.8453(2) 0.9900(4) 0.0580(10) Uani 1 1 d . . .
H22A H 0.7806 0.8352 1.0683 0.087 Uiso 1 1 calc R . .
H22B H 0.6826 0.8234 1.0311 0.087 Uiso 1 1 calc R . .
H22C H 0.7090 0.9042 0.9723 0.087 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 1.5005(19) . ?
S1 C23 1.781(3) . ?
S1 C22 1.791(3) . ?
Cl1 C19 1.754(3) . ?
N4 C15 1.364(3) . ?
N4 C16 1.408(3) . ?
N4 H4A 0.802(17) . ?
O1 C15 1.216(3) . ?
C19 C20 1.373(4) . ?
C19 C18 1.379(4) . ?
N1 C3 1.364(3) . ?
N1 N2 1.375(3) . ?
N1 C8 1.438(3) . ?
C3 C2 1.374(4) . ?
C3 N3 1.384(3) . ?
N2 C1 1.328(3) . ?
C17 C18 1.387(4) . ?
C17 C16 1.394(3) . ?
C17 H17A 0.9500 . ?
C2 C1 1.410(3) . ?
C2 H2A 0.9500 . ?
C15 N3 1.381(3) . ?
N3 H3A 0.863(17) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C12 C11 1.369(4) . ?
C12 C13 1.400(4) . ?
C12 H12A 0.9500 . ?
C8 C13 1.394(4) . ?
C8 C9 1.400(4) . ?
C18 H18A 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20A 0.9500 . ?
C1 C4 1.515(3) . ?
C21 C16 1.400(4) . ?
C21 H21A 0.9500 . ?
C14 C13 1.484(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C6 1.512(5) . ?
C4 C5 1.518(4) . ?
C4 C7 1.544(4) . ?
C11 C10 1.379(4) . ?
C11 H11A 0.9500 . ?
C9 C10 1.392(4) . ?
C9 H9A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 C23 106.70(14) . . ?
O2 S1 C22 105.63(15) . . ?
C23 S1 C22 97.48(15) . . ?
C15 N4 C16 125.5(2) . . ?
C15 N4 H4A 119(2) . . ?
C16 N4 H4A 115(2) . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 Cl1 119.9(2) . . ?
C18 C19 Cl1 118.8(2) . . ?
C3 N1 N2 111.5(2) . . ?
C3 N1 C8 129.5(2) . . ?
N2 N1 C8 118.98(19) . . ?
N1 C3 C2 107.0(2) . . ?
N1 C3 N3 119.7(2) . . ?
C2 C3 N3 133.3(2) . . ?
C1 N2 N1 104.6(2) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C3 C2 C1 105.0(2) . . ?
C3 C2 H2A 127.5 . . ?
C1 C2 H2A 127.5 . . ?
O1 C15 N4 124.5(2) . . ?
O1 C15 N3 123.4(2) . . ?
N4 C15 N3 112.0(2) . . ?
C15 N3 C3 123.1(2) . . ?
C15 N3 H3A 122(2) . . ?
C3 N3 H3A 115(2) . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C13 C8 C9 122.3(2) . . ?
C13 C8 N1 119.9(2) . . ?
C9 C8 N1 117.8(2) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C19 C20 C21 119.5(2) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
N2 C1 C2 111.9(2) . . ?
N2 C1 C4 120.4(2) . . ?
C2 C1 C4 127.6(2) . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?
C17 C16 C21 118.8(2) . . ?
C17 C16 N4 123.1(2) . . ?
C21 C16 N4 118.0(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C4 C1 108.7(2) . . ?
C6 C4 C5 111.0(3) . . ?
C1 C4 C5 110.5(2) . . ?
C6 C4 C7 107.7(3) . . ?
C1 C4 C7 110.8(2) . . ?
C5 C4 C7 108.2(3) . . ?
C8 C13 C12 116.7(2) . . ?
C8 C13 C14 122.3(2) . . ?
C12 C13 C14 121.0(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C3 C2 -0.2(3) . . . . ?
C8 N1 C3 C2 176.3(3) . . . . ?
N2 N1 C3 N3 -178.9(2) . . . . ?
C8 N1 C3 N3 -2.5(4) . . . . ?
C3 N1 N2 C1 0.3(3) . . . . ?
C8 N1 N2 C1 -176.5(2) . . . . ?
N1 C3 C2 C1 -0.1(3) . . . . ?
N3 C3 C2 C1 178.4(3) . . . . ?
C16 N4 C15 O1 -2.2(5) . . . . ?
C16 N4 C15 N3 179.4(2) . . . . ?
O1 C15 N3 C3 0.5(4) . . . . ?
N4 C15 N3 C3 178.9(2) . . . . ?
N1 C3 N3 C15 169.4(2) . . . . ?
C2 C3 N3 C15 -9.0(5) . . . . ?
C3 N1 C8 C13 86.0(4) . . . . ?
N2 N1 C8 C13 -97.8(3) . . . . ?
C3 N1 C8 C9 -96.9(3) . . . . ?
N2 N1 C8 C9 79.3(3) . . . . ?
C20 C19 C18 C17 0.3(4) . . . . ?
Cl1 C19 C18 C17 -179.4(2) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
Cl1 C19 C20 C21 -179.9(2) . . . . ?
N1 N2 C1 C2 -0.4(3) . . . . ?
N1 N2 C1 C4 176.2(2) . . . . ?
C3 C2 C1 N2 0.3(3) . . . . ?
C3 C2 C1 C4 -176.0(2) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C18 C17 C16 C21 1.8(4) . . . . ?
C18 C17 C16 N4 -176.4(2) . . . . ?
C20 C21 C16 C17 -1.1(4) . . . . ?
C20 C21 C16 N4 177.2(2) . . . . ?
C15 N4 C16 C17 -35.1(4) . . . . ?
C15 N4 C16 C21 146.7(3) . . . . ?
N2 C1 C4 C6 -106.2(3) . . . . ?
C2 C1 C4 C6 69.8(4) . . . . ?
N2 C1 C4 C5 131.7(3) . . . . ?
C2 C1 C4 C5 -52.2(4) . . . . ?
N2 C1 C4 C7 11.8(4) . . . . ?
C2 C1 C4 C7 -172.1(3) . . . . ?
C9 C8 C13 C12 -4.0(4) . . . . ?
N1 C8 C13 C12 173.0(2) . . . . ?
C9 C8 C13 C14 176.5(3) . . . . ?
N1 C8 C13 C14 -6.5(4) . . . . ?
C11 C12 C13 C8 2.1(4) . . . . ?
C11 C12 C13 C14 -178.3(3) . . . . ?
C13 C12 C11 C10 0.8(5) . . . . ?
C13 C8 C9 C10 2.8(4) . . . . ?
N1 C8 C9 C10 -174.2(2) . . . . ?
C12 C11 C10 C9 -2.1(5) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' nm in Cc'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            263.36
_reflns_d_resolution_high        0.7218
####################################################################### 
# 
# 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_compound-6HCl
_database_code_depnum_ccdc_archive 'CCDC 1474059'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-chlorophenyl)urea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 Cl N4 O , Cl , H2 O'
_chemical_formula_sum            'C21 H26 Cl2 N4 O2'
_chemical_formula_weight         437.36

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4909(3)
_cell_length_b                   15.4713(9)
_cell_length_c                   26.0024(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2208.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    176(2)
_cell_measurement_reflns_used    6278
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      176(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         371
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  1200
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            25147
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.99
_reflns_number_total             5022
_reflns_number_gt                4317
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.03P)²+0.6P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_number_reflns         5022
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.73220(12) 0.32112(4) 0.00936(2) 0.04350(18) Uani 1 1 d . . .
Cl2 Cl 1.08821(10) 0.56437(3) 0.256646(19) 0.02919(14) Uani 1 1 d . . .
O1 O 0.8676(3) 0.61812(10) 0.07309(6) 0.0401(5) Uani 1 1 d . . .
O2 O 0.4055(4) 0.96684(12) 0.23220(7) 0.0411(5) Uani 1 1 d . . .
N1 N 0.6038(3) 0.77141(11) 0.18794(6) 0.0222(4) Uani 1 1 d . . .
N2 N 0.4446(3) 0.83197(11) 0.16966(6) 0.0226(4) Uani 1 1 d . . .
H2B H 0.417(4) 0.8765(14) 0.1887(8) 0.024(6) Uiso 1 1 d . . .
C3 C 0.6487(4) 0.71435(13) 0.14998(8) 0.0245(5) Uani 1 1 d . . .
C13 C 0.4156(4) 0.94409(15) 0.06524(9) 0.0357(5) Uani 1 1 d . . .
H13A H 0.5444 0.9160 0.0452 0.054 Uiso 1 1 calc R . .
H13B H 0.4886 0.9768 0.0936 0.054 Uiso 1 1 calc R . .
H13C H 0.3239 0.9835 0.0430 0.054 Uiso 1 1 calc R . .
N4 N 1.0895(4) 0.54586(12) 0.13424(7) 0.0301(4) Uani 1 1 d . . .
H4A H 1.114(4) 0.5410(14) 0.1653(9) 0.029(6) Uiso 1 1 d . . .
C15 C 0.9206(5) 0.60370(14) 0.11747(8) 0.0297(5) Uani 1 1 d . . .
C9 C 0.8926(4) 0.82048(15) 0.25231(8) 0.0348(5) Uani 1 1 d . . .
H9A H 0.9731 0.8538 0.2267 0.042 Uiso 1 1 calc R . .
C16 C 1.2404(4) 0.49442(13) 0.10269(8) 0.0255(5) Uani 1 1 d . . .
C11 C 0.2427(4) 0.87500(13) 0.08705(7) 0.0237(5) Uani 1 1 d . . .
C5 C 0.5686(5) 0.72364(14) 0.27688(8) 0.0278(5) Uani 1 1 d . . .
H5A H 0.4284 0.6913 0.2675 0.033 Uiso 1 1 calc R . .
N3 N 0.8078(4) 0.64736(12) 0.15840(7) 0.0296(5) Uani 1 1 d . . .
H3A H 0.860(4) 0.6399(14) 0.1887(9) 0.024(6) Uiso 1 1 d . . .
C1 C 0.3941(4) 0.81474(13) 0.12029(7) 0.0221(4) Uani 1 1 d . . .
C6 C 0.6516(5) 0.72237(15) 0.32726(8) 0.0322(6) Uani 1 1 d . . .
C12 C 0.0434(4) 0.91964(15) 0.11856(8) 0.0319(5) Uani 1 1 d . . .
H12A H 0.1180 0.9516 0.1470 0.048 Uiso 1 1 calc R . .
H12B H -0.0685 0.8761 0.1323 0.048 Uiso 1 1 calc R . .
H12C H -0.0467 0.9598 0.0965 0.048 Uiso 1 1 calc R . .
C4 C 0.6905(4) 0.77197(13) 0.24059(8) 0.0223(4) Uani 1 1 d . . .
C7 C 0.8554(5) 0.77131(17) 0.33932(9) 0.0383(6) Uani 1 1 d . . .
H7A H 0.9139 0.7718 0.3737 0.046 Uiso 1 1 calc R . .
C20 C 1.6001(5) 0.40728(15) 0.09536(9) 0.0366(6) Uani 1 1 d . . .
H20A H 1.7440 0.3839 0.1101 0.044 Uiso 1 1 calc R . .
C2 C 0.5160(4) 0.73956(13) 0.10689(8) 0.0259(5) Uani 1 1 d . . .
H2A H 0.5102 0.7109 0.0746 0.031 Uiso 1 1 calc R . .
C21 C 1.4492(4) 0.45994(15) 0.12436(8) 0.0326(5) Uani 1 1 d . . .
H21A H 1.4890 0.4724 0.1591 0.039 Uiso 1 1 calc R . .
C14 C 0.1283(5) 0.82404(16) 0.04289(9) 0.0357(6) Uani 1 1 d . . .
H14A H 0.2573 0.7985 0.0217 0.054 Uiso 1 1 calc R . .
H14B H 0.0293 0.8629 0.0217 0.054 Uiso 1 1 calc R . .
H14C H 0.0250 0.7780 0.0569 0.054 Uiso 1 1 calc R . .
C18 C 1.3363(4) 0.42248(16) 0.02315(9) 0.0361(6) Uani 1 1 d . . .
H18A H 1.2979 0.4096 -0.0116 0.043 Uiso 1 1 calc R . .
C8 C 0.9748(5) 0.81921(18) 0.30251(9) 0.0453(7) Uani 1 1 d . . .
H8A H 1.1151 0.8517 0.3117 0.054 Uiso 1 1 calc R . .
C19 C 1.5412(4) 0.38896(14) 0.04510(9) 0.0303(5) Uani 1 1 d . . .
C17 C 1.1842(4) 0.47538(16) 0.05180(9) 0.0352(6) Uani 1 1 d . . .
H17A H 1.0412 0.4987 0.0366 0.042 Uiso 1 1 calc R . .
C10 C 0.5212(6) 0.66988(18) 0.36767(10) 0.0582(9) Uani 1 1 d . . .
H10A H 0.3817 0.6403 0.3521 0.087 Uiso 1 1 calc R . .
H10B H 0.4639 0.7082 0.3951 0.087 Uiso 1 1 calc R . .
H10C H 0.6332 0.6270 0.3821 0.087 Uiso 1 1 calc R . .
H2C H 0.294(7) 1.000(2) 0.2368(12) 0.062(11) Uiso 1 1 d . . .
H2D H 0.525(7) 0.999(2) 0.2308(13) 0.078(13) Uiso 1 1 d . . .


_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
Cl1 C19 1.751(2) . ?
O1 C15 1.211(3) . ?
N1 C3 1.347(3) . ?
N1 N2 1.366(2) . ?
N1 C4 1.450(2) . ?
N2 C1 1.340(3) . ?
C3 N3 1.373(3) . ?
C3 C2 1.392(3) . ?
C13 C11 1.538(3) . ?
N4 C15 1.361(3) . ?
N4 C16 1.412(3) . ?
C15 N3 1.404(3) . ?
C9 C4 1.374(3) . ?
C9 C8 1.381(3) . ?
C16 C21 1.384(3) . ?
C16 C17 1.390(3) . ?
C11 C1 1.519(3) . ?
C11 C14 1.528(3) . ?
C11 C12 1.531(3) . ?
C5 C4 1.377(3) . ?
C5 C6 1.387(3) . ?
C1 C2 1.386(3) . ?
C6 C7 1.387(3) . ?
C6 C10 1.509(3) . ?
C7 C8 1.376(3) . ?
C20 C19 1.376(3) . ?
C20 C21 1.385(3) . ?
C18 C19 1.364(3) . ?
C18 C17 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 N2 108.16(16) . . ?
C3 N1 C4 129.48(17) . . ?
N2 N1 C4 122.30(16) . . ?
C1 N2 N1 109.22(17) . . ?
N1 C3 N3 119.64(18) . . ?
N1 C3 C2 108.07(18) . . ?
N3 C3 C2 132.27(19) . . ?
C15 N4 C16 125.79(19) . . ?
O1 C15 N4 126.2(2) . . ?
O1 C15 N3 121.8(2) . . ?
N4 C15 N3 111.98(18) . . ?
C4 C9 C8 117.8(2) . . ?
C21 C16 C17 119.3(2) . . ?
C21 C16 N4 117.83(19) . . ?
C17 C16 N4 122.8(2) . . ?
C1 C11 C14 109.62(17) . . ?
C1 C11 C12 111.31(16) . . ?
C14 C11 C12 109.94(19) . . ?
C1 C11 C13 107.38(18) . . ?
C14 C11 C13 109.59(18) . . ?
C12 C11 C13 108.96(18) . . ?
C4 C5 C6 119.7(2) . . ?
C3 N3 C15 121.52(18) . . ?
N2 C1 C2 107.90(19) . . ?
N2 C1 C11 122.43(18) . . ?
C2 C1 C11 129.52(18) . . ?
C5 C6 C7 118.1(2) . . ?
C5 C6 C10 120.6(2) . . ?
C7 C6 C10 121.3(2) . . ?
C9 C4 C5 122.5(2) . . ?
C9 C4 N1 118.56(19) . . ?
C5 C4 N1 118.96(18) . . ?
C8 C7 C6 121.4(2) . . ?
C19 C20 C21 119.8(2) . . ?
C1 C2 C3 106.60(18) . . ?
C16 C21 C20 120.0(2) . . ?
C19 C18 C17 119.8(2) . . ?
C7 C8 C9 120.6(2) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 Cl1 120.00(18) . . ?
C20 C19 Cl1 119.12(19) . . ?
C18 C17 C16 120.2(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
C3 N1 N2 C1 -1.5(2) . . . . ?
C4 N1 N2 C1 -179.09(18) . . . . ?
N2 N1 C3 N3 178.88(19) . . . . ?
C4 N1 C3 N3 -3.8(3) . . . . ?
N2 N1 C3 C2 0.2(2) . . . . ?
C4 N1 C3 C2 177.5(2) . . . . ?
C16 N4 C15 O1 2.5(4) . . . . ?
C16 N4 C15 N3 -177.4(2) . . . . ?
C15 N4 C16 C21 160.3(2) . . . . ?
C15 N4 C16 C17 -21.5(4) . . . . ?
N1 C3 N3 C15 -159.2(2) . . . . ?
C2 C3 N3 C15 19.1(4) . . . . ?
O1 C15 N3 C3 -6.3(3) . . . . ?
N4 C15 N3 C3 173.6(2) . . . . ?
N1 N2 C1 C2 2.2(2) . . . . ?
N1 N2 C1 C11 -173.68(18) . . . . ?
C14 C11 C1 N2 -156.2(2) . . . . ?
C12 C11 C1 N2 -34.4(3) . . . . ?
C13 C11 C1 N2 84.8(2) . . . . ?
C14 C11 C1 C2 28.8(3) . . . . ?
C12 C11 C1 C2 150.7(2) . . . . ?
C13 C11 C1 C2 -90.2(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C10 -180.0(2) . . . . ?
C8 C9 C4 C5 0.6(3) . . . . ?
C8 C9 C4 N1 -179.0(2) . . . . ?
C6 C5 C4 C9 -0.7(3) . . . . ?
C6 C5 C4 N1 179.0(2) . . . . ?
C3 N1 C4 C9 95.8(3) . . . . ?
N2 N1 C4 C9 -87.2(2) . . . . ?
C3 N1 C4 C5 -83.8(3) . . . . ?
N2 N1 C4 C5 93.2(2) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C10 C6 C7 C8 180.0(3) . . . . ?
N2 C1 C2 C3 -2.1(2) . . . . ?
C11 C1 C2 C3 173.5(2) . . . . ?
N1 C3 C2 C1 1.1(2) . . . . ?
N3 C3 C2 C1 -177.3(2) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
N4 C16 C21 C20 178.4(2) . . . . ?
C19 C20 C21 C16 -0.4(4) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C4 C9 C8 C7 -0.6(4) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C17 C18 C19 Cl1 179.28(19) . . . . ?
C21 C20 C19 C18 0.5(4) . . . . ?
C21 C20 C19 Cl1 -179.17(19) . . . . ?
C19 C18 C17 C16 0.2(4) . . . . ?
C21 C16 C17 C18 -0.1(4) . . . . ?
N4 C16 C17 C18 -178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag

N2 H2B O2 . . 1_555 0.86(2) 1.80(2) 2.654(2) 171(2) yes
N3 H3A Cl2 . . 1_555 0.85(2) 2.46(2) 3.247(2) 155(2) yes
N4 H4A Cl2 . . 1_555 0.82(2) 2.41(2) 3.196(2) 161(2) yes
O2 H2C Cl2 . . 3_655 0.81(4) 2.33(4) 3.116(2) 165(3) yes
O2 H2D Cl2 . . 3_755 0.82(4) 2.38(4) 3.176(2) 164(3) yes
C5 H5A Cl2 . . 1_455 0.95 2.72 3.648(3) 164 yes

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 

_shelx_title                     ' km in P2(1)2(1)2(1)'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            164.06
_reflns_d_resolution_high        0.7571
