# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_ngs-286
_database_code_depnum_ccdc_archive 'CCDC 1024256'
_audit_update_record             
;
2014-09-15 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_audit_creation_date             2014-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            Quinolinone
_chemical_name_systematic        
3,7,7-trimethyl-4-phenyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]quinolin-5(4H)-one
_chemical_formula_moiety         'C19 H21 N3 O'
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39
_chemical_melting_point          503-505
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1735(11)
_cell_length_b                   14.3043(10)
_cell_length_c                   11.2897(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.376(8)
_cell_angle_gamma                90.00
_cell_volume                     1632.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    292.34(10)
_cell_measurement_theta_max      25.8160
_cell_measurement_theta_min      3.3700
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7067
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      292.34(10)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2061
_reflns_number_total             3707
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1646
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C15(H15), C16(H16), C19(H19), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.94805(15) 0.33142(10) 0.60206(14) 0.0480(4) Uani 1 d . . .
N3 N 0.59747(18) 0.11724(12) 0.50971(15) 0.0450(5) Uani 1 d . . .
H3 H 0.5368 0.0972 0.4566 0.054 Uiso 1 calc . . R
N2 N 0.53972(19) 0.01195(12) 0.65998(16) 0.0452(5) Uani 1 d . . .
N1 N 0.5825(2) 0.00575(12) 0.77844(16) 0.0476(5) Uani 1 d . . .
H1 H 0.5565 -0.0368 0.8244 0.057 Uiso 1 calc . . R
C10 C 0.8723(2) 0.28691(14) 0.52826(19) 0.0369(5) Uani 1 d . . .
C2 C 0.6840(2) 0.12910(14) 0.71913(18) 0.0370(5) Uani 1 d . . .
C11 C 0.7736(2) 0.22470(14) 0.56552(18) 0.0369(5) Uani 1 d . . .
C6 C 0.6909(2) 0.17894(14) 0.48082(18) 0.0369(5) Uani 1 d . . .
C5 C 0.6030(2) 0.08761(14) 0.62723(19) 0.0395(5) Uani 1 d . . .
C14 C 0.6980(2) 0.30282(15) 0.74860(19) 0.0414(5) Uani 1 d . . .
C3 C 0.6699(2) 0.07342(15) 0.81612(19) 0.0429(6) Uani 1 d . . .
C1 C 0.7613(2) 0.21631(14) 0.69884(18) 0.0394(5) Uani 1 d . . .
H1A H 0.8504 0.2092 0.7407 0.047 Uiso 1 calc . . R
C8 C 0.7574(2) 0.28308(15) 0.31584(19) 0.0433(6) Uani 1 d . . .
C7 C 0.6972(2) 0.19044(15) 0.34951(18) 0.0448(6) Uani 1 d . . .
H7A H 0.6084 0.1856 0.3087 0.054 Uiso 1 calc . . R
H7B H 0.7491 0.1397 0.3217 0.054 Uiso 1 calc . . R
C9 C 0.8863(2) 0.29643(17) 0.3975(2) 0.0486(6) Uani 1 d . . .
H9A H 0.9501 0.2508 0.3762 0.058 Uiso 1 calc . . R
H9B H 0.9213 0.3580 0.3833 0.058 Uiso 1 calc . . R
C15 C 0.5955(3) 0.34842(16) 0.6827(2) 0.0540(6) Uani 1 d . . .
H15 H 0.5666 0.3278 0.6061 0.065 Uiso 1 calc . . R
C16 C 0.5346(3) 0.42485(18) 0.7292(3) 0.0684(8) Uani 1 d . . .
H16 H 0.4659 0.4552 0.6834 0.082 Uiso 1 calc . . R
C12 C 0.7846(3) 0.28018(19) 0.1855(2) 0.0631(7) Uani 1 d . . .
H12A H 0.8425 0.2288 0.1737 0.095 Uiso 1 calc . . GR
H12B H 0.8256 0.3376 0.1655 0.095 Uiso 1 calc . . GR
H12C H 0.7027 0.2723 0.1353 0.095 Uiso 1 calc . . GR
C13 C 0.6637(3) 0.36382(17) 0.3328(2) 0.0604(7) Uani 1 d . . .
H13A H 0.5822 0.3546 0.2826 0.091 Uiso 1 calc . . GR
H13B H 0.7036 0.4215 0.3120 0.091 Uiso 1 calc . . GR
H13C H 0.6462 0.3662 0.4146 0.091 Uiso 1 calc . . GR
C19 C 0.7387(3) 0.33506(17) 0.8620(2) 0.0552(7) Uani 1 d . . .
H19 H 0.8077 0.3053 0.9081 0.066 Uiso 1 calc . . R
C17 C 0.5750(3) 0.45583(19) 0.8419(3) 0.0725(9) Uani 1 d . . .
H17 H 0.5331 0.5065 0.8732 0.087 Uiso 1 calc . . R
C4 C 0.7315(3) 0.07721(17) 0.9416(2) 0.0611(7) Uani 1 d . . .
H4A H 0.6734 0.1093 0.9894 0.092 Uiso 1 calc . . GR
H4B H 0.8142 0.1100 0.9453 0.092 Uiso 1 calc . . GR
H4C H 0.7466 0.0148 0.9713 0.092 Uiso 1 calc . . GR
C18 C 0.6766(3) 0.41227(18) 0.9079(3) 0.0712(9) Uani 1 d . . .
H18 H 0.7052 0.4338 0.9841 0.085 Uiso 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
O1 C10 1.245(2) . ?
N3 C6 1.363(3) . ?
N3 C5 1.388(3) . ?
N2 N1 1.363(2) . ?
N2 C5 1.333(3) . ?
N1 C3 1.351(3) . ?
C10 C11 1.439(3) . ?
C10 C9 1.505(3) . ?
C2 C5 1.385(3) . ?
C2 C3 1.374(3) . ?
C2 C1 1.506(3) . ?
C11 C6 1.368(3) . ?
C11 C1 1.529(3) . ?
C6 C7 1.500(3) . ?
C14 C1 1.530(3) . ?
C14 C15 1.376(3) . ?
C14 C19 1.380(3) . ?
C3 C4 1.485(3) . ?
C8 C7 1.525(3) . ?
C8 C9 1.528(3) . ?
C8 C12 1.528(3) . ?
C8 C13 1.523(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.366(4) . ?
C19 C18 1.400(3) . ?
C17 C18 1.356(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N3 C5 118.10(17) . . ?
C5 N2 N1 102.34(16) . . ?
C3 N1 N2 112.93(18) . . ?
O1 C10 C11 121.37(19) . . ?
O1 C10 C9 119.44(19) . . ?
C11 C10 C9 119.17(18) . . ?
C5 C2 C1 121.23(19) . . ?
C3 C2 C5 104.05(19) . . ?
C3 C2 C1 134.7(2) . . ?
C10 C11 C1 118.18(17) . . ?
C6 C11 C10 119.10(19) . . ?
C6 C11 C1 122.65(19) . . ?
N3 C6 C11 122.24(19) . . ?
N3 C6 C7 114.52(17) . . ?
C11 C6 C7 123.22(19) . . ?
N2 C5 N3 122.93(19) . . ?
N2 C5 C2 113.94(19) . . ?
C2 C5 N3 122.89(19) . . ?
C15 C14 C1 120.6(2) . . ?
C15 C14 C19 118.3(2) . . ?
C19 C14 C1 121.1(2) . . ?
N1 C3 C2 106.71(19) . . ?
N1 C3 C4 121.3(2) . . ?
C2 C3 C4 132.0(2) . . ?
C2 C1 C11 108.42(16) . . ?
C2 C1 C14 111.47(18) . . ?
C11 C1 C14 112.43(17) . . ?
C7 C8 C9 107.41(18) . . ?
C7 C8 C12 109.69(18) . . ?
C12 C8 C9 110.43(19) . . ?
C13 C8 C7 110.7(2) . . ?
C13 C8 C9 109.66(19) . . ?
C13 C8 C12 108.94(19) . . ?
C6 C7 C8 113.82(17) . . ?
C10 C9 C8 114.34(18) . . ?
C14 C15 C16 120.8(2) . . ?
C17 C16 C15 120.5(3) . . ?
C14 C19 C18 120.4(2) . . ?
C18 C17 C16 119.6(3) . . ?
C17 C18 C19 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_NGS-306
_database_code_depnum_ccdc_archive 'CCDC 1024257'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C17 H17 Cl N4 O'
_chemical_formula_sum            'C17 H17 Cl N4 O'
_chemical_formula_weight         328.80
_chemical_oxdiff_formula         C17H17N4OCl
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.0023(11)
_cell_length_b                   12.317(2)
_cell_length_c                   12.460(2)
_cell_angle_alpha                67.981(17)
_cell_angle_beta                 77.245(15)
_cell_angle_gamma                80.977(15)
_cell_volume                     830.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    291.9(9)
_cell_measurement_theta_max      26.2160
_cell_measurement_theta_min      4.2660
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.3154
_exptl_crystal_F_000             344.4188
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6065
_diffrn_reflns_theta_full        28.735889
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_temperature      291.9(9)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   25.00   1.0000    3.1100
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -99.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   50.00   1.0000    3.1100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -37.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   49.00   1.0000    3.1100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -99.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   46.00   1.0000    3.1100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   90.00   1.0000    3.1100
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000  -60.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0115693000
_diffrn_orient_matrix_UB_12      0.0609201000
_diffrn_orient_matrix_UB_13      -0.0171361000
_diffrn_orient_matrix_UB_21      -0.0170248000
_diffrn_orient_matrix_UB_22      -0.0056999000
_diffrn_orient_matrix_UB_23      0.0599814000
_diffrn_orient_matrix_UB_31      0.1198137000
_diffrn_orient_matrix_UB_32      -0.0118729000
_diffrn_orient_matrix_UB_33      -0.0010212000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              16
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2469
_reflns_number_total             3734
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.419484
_refine_diff_density_min         -0.668595
_refine_diff_density_rms         0.060648
_refine_ls_d_res_high            0.739154
_refine_ls_d_res_low             6.008318
_refine_ls_goodness_of_fit_ref   1.035773
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.084997
_refine_ls_R_factor_gt           0.053494
_refine_ls_restrained_S_all      1.035773
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.2554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.140108
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl 0.1660(2) 0.52338(7) 0.85196(8) 0.1248(5) Uani 1.000000 .
O1 O 0.7774(3) 0.09408(17) 0.74964(16) 0.0711(5) Uani 1.000000 .
N4 N 0.2160(3) 0.00116(15) 0.59473(14) 0.0405(4) Uani 1.000000 .
N1 N 0.3168(3) 0.19520(15) 0.51347(14) 0.0433(4) Uani 1.000000 .
N3 N 0.0646(3) 0.15291(15) 0.43459(14) 0.0453(4) Uani 1.000000 .
N2 N 0.2635(3) 0.29851(17) 0.42737(16) 0.0564(5) Uani 1.000000 .
C3 C 0.1965(3) 0.11194(18) 0.51595(16) 0.0380(4) Uani 1.000000 .
C4 C 0.3541(3) -0.02328(18) 0.67674(16) 0.0369(4) Uani 1.000000 .
C9 C 0.4815(3) 0.05905(19) 0.67576(17) 0.0406(5) Uani 1.000000 .
C1 C 0.4736(3) 0.18490(19) 0.59228(18) 0.0433(5) Uani 1.000000 .
C8 C 0.6445(3) 0.0252(2) 0.75630(19) 0.0491(5) Uani 1.000000 .
C5 C 0.3543(3) -0.14572(18) 0.76378(17) 0.0424(5) Uani 1.000000 .
C10 C 0.3933(4) 0.27307(19) 0.65492(18) 0.0458(5) Uani 1.000000 .
C6 C 0.4280(4) -0.1579(2) 0.87846(18) 0.0473(5) Uani 1.000000 .
C2 C 0.1136(4) 0.2671(2) 0.3847(2) 0.0545(6) Uani 1.000000 .
C7 C 0.6516(4) -0.0973(2) 0.8435(2) 0.0552(6) Uani 1.000000 .
C11 C 0.5307(5) 0.3588(2) 0.6409(2) 0.0662(7) Uani 1.000000 .
C17 C 0.2423(4) -0.0994(2) 0.9499(2) 0.0616(7) Uani 1.000000 .
C15 C 0.1822(4) 0.2684(2) 0.7266(2) 0.0609(6) Uani 1.000000 .
C14 C 0.1099(5) 0.3462(2) 0.7858(2) 0.0737(8) Uani 1.000000 .
C16 C 0.4696(5) -0.2874(2) 0.9502(2) 0.0702(8) Uani 1.000000 .
C13 C 0.2517(6) 0.4287(2) 0.7727(2) 0.0720(8) Uani 1.000000 .
C12 C 0.4591(6) 0.4372(2) 0.7002(3) 0.0829(9) Uani 1.000000 .
H12 H 0.5522(6) 0.4951(2) 0.6905(3) 0.0995(11) Uiso 1.000000 R
H11 H 0.6725(5) 0.3643(2) 0.5913(2) 0.0795(9) Uiso 1.000000 R
H15 H 0.0865(4) 0.2120(2) 0.7354(2) 0.0731(8) Uiso 1.000000 R
H14 H -0.0333(5) 0.3426(2) 0.8339(2) 0.0884(9) Uiso 1.000000 R
H4 H 0.1431(3) -0.05300(15) 0.59342(14) 0.0485(5) Uiso 1.000000 R
H1 H 0.6269(3) 0.20174(19) 0.54574(18) 0.0520(6) Uiso 1.000000 R
H5a H 0.2016(3) -0.17178(18) 0.78218(17) 0.0509(6) Uiso 1.000000 R
H5b H 0.4573(3) -0.19695(18) 0.72836(17) 0.0509(6) Uiso 1.000000 R
H2 H 0.0444(4) 0.3203(2) 0.3234(2) 0.0655(7) Uiso 1.000000 R
H7a H 0.7725(4) -0.1446(2) 0.8113(2) 0.0663(7) Uiso 1.000000 R
H7b H 0.6922(4) -0.0958(2) 0.9141(2) 0.0663(7) Uiso 1.000000 R
H17a H 0.216(2) -0.0177(4) 0.9042(6) 0.0924(10) Uiso 1.000000 G
H17b H 0.1028(9) -0.1370(10) 0.9694(12) 0.0924(10) Uiso 1.000000 G
H17c H 0.2914(13) -0.1069(13) 1.0208(7) 0.0924(10) Uiso 1.000000 G
H16a H 0.3315(10) -0.3255(4) 0.9675(14) 0.1053(11) Uiso 1.000000 G
H16b H 0.589(2) -0.3231(4) 0.9060(7) 0.1053(11) Uiso 1.000000 G
H16c H 0.514(3) -0.2953(2) 1.0223(8) 0.1053(11) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.747(3) .
O1 C8 1.222(2) .
N4 C3 1.355(3) .
N4 C4 1.373(2) .
N4 H4 0.8600 .
N1 N2 1.369(3) .
N1 C3 1.332(2) .
N1 C1 1.464(2) .
N3 C3 1.324(2) .
N3 C2 1.359(3) .
N2 C2 1.310(3) .
C4 C9 1.358(3) .
C4 C5 1.491(3) .
C9 C1 1.509(3) .
C9 C8 1.459(3) .
C1 C10 1.525(3) .
C1 H1 0.9800 .
C8 C7 1.494(3) .
C5 C6 1.535(3) .
C5 H5a 0.9700 .
C5 H5b 0.9700 .
C10 C11 1.378(3) .
C10 C15 1.375(3) .
C6 C7 1.536(3) .
C6 C17 1.531(3) .
C6 C16 1.520(3) .
C2 H2 0.9300 .
C7 H7a 0.9700 .
C7 H7b 0.9700 .
C11 C12 1.388(4) .
C11 H11 0.9300 .
C17 H17a 0.9600 .
C17 H17b 0.9600 .
C17 H17c 0.9600 .
C15 C14 1.381(3) .
C15 H15 0.9300 .
C14 C13 1.367(4) .
C14 H14 0.9300 .
C16 H16a 0.9600 .
C16 H16b 0.9600 .
C16 H16c 0.9600 .
C13 C12 1.360(4) .
C12 H12 0.9300 .

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
C4 N4 C3 118.94(16) . .
H4 N4 C3 120.53(10) . .
H4 N4 C4 120.53(11) . .
C3 N1 N2 109.35(16) . .
C1 N1 N2 123.12(16) . .
C1 N1 C3 127.45(17) . .
C2 N3 C3 101.12(16) . .
C2 N2 N1 101.55(17) . .
N1 C3 N4 121.10(17) . .
N3 C3 N4 127.45(17) . .
N3 C3 N1 111.44(18) . .
C9 C4 N4 121.42(19) . .
C5 C4 N4 115.01(16) . .
C5 C4 C9 123.57(17) . .
C1 C9 C4 124.09(17) . .
C8 C9 C4 119.3(2) . .
C8 C9 C1 116.59(17) . .
C9 C1 N1 106.83(15) . .
C10 C1 N1 110.05(17) . .
C10 C1 C9 113.07(16) . .
H1 C1 N1 108.93(10) . .
H1 C1 C9 108.93(10) . .
H1 C1 C10 108.93(10) . .
C9 C8 O1 120.8(2) . .
C7 C8 O1 120.86(19) . .
C7 C8 C9 118.32(18) . .
C6 C5 C4 113.39(16) . .
H5a C5 C4 108.89(10) . .
H5a C5 C6 108.89(11) . .
H5b C5 C4 108.89(10) . .
H5b C5 C6 108.89(11) . .
H5b C5 H5a 107.7 . .
C11 C10 C1 120.7(2) . .
C15 C10 C1 120.61(18) . .
C15 C10 C11 118.7(2) . .
C7 C6 C5 106.89(17) . .
C17 C6 C5 110.38(17) . .
C17 C6 C7 110.47(18) . .
C16 C6 C5 109.28(18) . .
C16 C6 C7 110.01(19) . .
C16 C6 C17 109.8(2) . .
N2 C2 N3 116.5(2) . .
H2 C2 N3 121.73(11) . .
H2 C2 N2 121.73(13) . .
C6 C7 C8 115.44(17) . .
H7a C7 C8 108.42(12) . .
H7a C7 C6 108.42(12) . .
H7b C7 C8 108.42(11) . .
H7b C7 C6 108.42(11) . .
H7b C7 H7a 107.5 . .
C12 C11 C10 120.5(3) . .
H11 C11 C10 119.76(15) . .
H11 C11 C12 119.76(17) . .
H17a C17 C6 109.5 . .
H17b C17 C6 109.5 . .
H17b C17 H17a 109.5 . .
H17c C17 C6 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .
C14 C15 C10 121.1(2) . .
H15 C15 C10 119.47(13) . .
H15 C15 C14 119.47(16) . .
C13 C14 C15 119.1(3) . .
H14 C14 C15 120.43(16) . .
H14 C14 C13 120.43(18) . .
H16a C16 C6 109.5 . .
H16b C16 C6 109.5 . .
H16b C16 H16a 109.5 . .
H16c C16 C6 109.5 . .
H16c C16 H16a 109.5 . .
H16c C16 H16b 109.5 . .
C14 C13 Cl1 119.3(3) . .
C12 C13 Cl1 119.6(2) . .
C12 C13 C14 121.1(2) . .
C13 C12 C11 119.5(2) . .
H12 C12 C11 120.27(17) . .
H12 C12 C13 120.27(16) . .

_chemical_name_systematic        
9-(4-chlorophenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one
_chemical_name_common            Quinazolinone
_chemical_melting_point          570-571
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
