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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_dv_2_rt
_database_code_depnum_ccdc_archive 'CCDC 1505629'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
4-(3-(4-chlorophenyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)benzonitrile
_chemical_formula_moiety         C21H12ClN3O
_chemical_formula_sum            C21H12ClN3O
_chemical_formula_weight         357.79
_chemical_melting_point          >473
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'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   6.030(4)
_cell_length_b                   11.743(7)
_cell_length_c                   12.159(8)
_cell_angle_alpha                103.26(3)
_cell_angle_beta                 94.68(3)
_cell_angle_gamma                92.030(17)
_cell_volume                     834.0(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8459
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 600
	           Slice: -69.0000 - 111.0000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.071390
_diffrn_orient_matrix_UB_12      -0.120359
_diffrn_orient_matrix_UB_13      -0.090483
_diffrn_orient_matrix_UB_21      0.081113
_diffrn_orient_matrix_UB_22      0.027987
_diffrn_orient_matrix_UB_23      0.017765
_diffrn_orient_matrix_UB_31      0.023084
_diffrn_orient_matrix_UB_32      -0.047225
_diffrn_orient_matrix_UB_33      0.066620
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             3785
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.007(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0962
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2906
_refine_ls_wR_factor_ref         0.3211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C15-N3
 1.2 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C10(H10), C21(H21), C11(H11), C7(H7), C20(H20), C4(H4),
 C17(H17), C6(H6), C5(H5), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.1932(2) 0.63240(10) 0.67171(12) 0.1041(5) Uani 1 1 d . . . . .
N2 N 0.2864(4) 0.2477(2) 0.92614(19) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.1994(4) 0.1614(2) 0.7305(2) 0.0581(6) Uani 1 1 d . . . . .
C15 C 0.5329(5) 0.0818(3) 0.2359(3) 0.0600(7) Uani 1 1 d D . . . .
C8 C 0.1558(5) 0.1765(2) 0.8387(2) 0.0536(7) Uani 1 1 d . . . . .
C1 C 0.3785(4) 0.2237(2) 0.7095(2) 0.0525(7) Uani 1 1 d . . . . .
C2 C 0.5129(5) 0.3047(2) 0.7922(2) 0.0522(6) Uani 1 1 d . . . . .
C3 C 0.4770(5) 0.3153(3) 0.9073(2) 0.0562(7) Uani 1 1 d . . . . .
C9 C 0.4236(4) 0.1932(3) 0.5882(2) 0.0543(7) Uani 1 1 d . . . . .
C14 C 0.6290(4) 0.1498(3) 0.5558(2) 0.0572(7) Uani 1 1 d . . . . .
H14 H 0.7424 0.1454 0.6110 0.069 Uiso 1 1 calc R . . . .
C13 C 0.6627(5) 0.1138(3) 0.4432(3) 0.0601(7) Uani 1 1 d . . . . .
H13 H 0.7979 0.0842 0.4220 0.072 Uiso 1 1 calc R . . . .
C16 C 0.6869(5) 0.3845(3) 0.7644(2) 0.0568(7) Uani 1 1 d . . . . .
C12 C 0.4953(5) 0.1219(3) 0.3616(2) 0.0587(7) Uani 1 1 d . . . . .
C10 C 0.2581(5) 0.1991(3) 0.5046(2) 0.0612(8) Uani 1 1 d . . . . .
H10 H 0.1210 0.2265 0.5252 0.073 Uiso 1 1 calc R . . . .
C21 C 0.8861(5) 0.4150(3) 0.8319(3) 0.0602(7) Uani 1 1 d . . . . .
H21 H 0.9135 0.3854 0.8961 0.072 Uiso 1 1 calc R . . . .
C11 C 0.2915(5) 0.1652(3) 0.3911(3) 0.0639(8) Uani 1 1 d . . . . .
H11 H 0.1800 0.1712 0.3355 0.077 Uiso 1 1 calc R . . . .
C7 C -0.0366(5) 0.1178(3) 0.8633(3) 0.0649(8) Uani 1 1 d . . . . .
H7 H -0.1274 0.0696 0.8040 0.078 Uiso 1 1 calc R . . . .
C20 C 1.0457(5) 0.4898(3) 0.8040(3) 0.0715(9) Uani 1 1 d . . . . .
H20 H 1.1810 0.5085 0.8482 0.086 Uiso 1 1 calc R . . . .
C4 C 0.2342(6) 0.2594(3) 1.0380(3) 0.0703(9) Uani 1 1 d . . . . .
H4 H 0.3266 0.3059 1.0976 0.084 Uiso 1 1 calc R . . . .
C19 C 1.0013(6) 0.5361(3) 0.7102(3) 0.0709(9) Uani 1 1 d . . . . .
C17 C 0.6447(6) 0.4361(3) 0.6732(3) 0.0707(9) Uani 1 1 d . . . . .
H17 H 0.5079 0.4196 0.6300 0.085 Uiso 1 1 calc R . . . .
C6 C -0.0914(7) 0.1300(3) 0.9710(3) 0.0727(9) Uani 1 1 d . . . . .
H6 H -0.2183 0.0914 0.9866 0.087 Uiso 1 1 calc R . . . .
C5 C 0.0509(7) 0.2035(4) 1.0592(3) 0.0788(10) Uani 1 1 d . . . . .
H5 H 0.0161 0.2133 1.1338 0.095 Uiso 1 1 calc R . . . .
C18 C 0.7997(7) 0.5111(3) 0.6450(3) 0.0742(9) Uani 1 1 d . . . . .
H18 H 0.7690 0.5443 0.5833 0.089 Uiso 1 1 calc R . . . .
N3 N 0.5594(7) 0.0551(4) 0.1558(4) 0.1005(11) Uani 1 1 d D . . . .
O1 O 0.5860(5) 0.3741(3) 0.9923(2) 0.0927(9) Uani 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 1.753(3) . ?
N2 C8 1.363(4) . ?
N2 C3 1.438(4) . ?
N2 C4 1.399(4) . ?
N1 C8 1.336(4) . ?
N1 C1 1.357(4) . ?
C15 C12 1.531(4) . ?
C15 N3 0.980(5) . ?
C8 C7 1.416(4) . ?
C1 C2 1.395(4) . ?
C1 C9 1.486(4) . ?
C2 C3 1.411(4) . ?
C2 C16 1.492(4) . ?
C3 O1 1.228(4) . ?
C9 C14 1.408(4) . ?
C9 C10 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(4) . ?
C16 C21 1.385(4) . ?
C16 C17 1.391(5) . ?
C12 C11 1.389(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.394(5) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.355(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.338(5) . ?
C19 C18 1.379(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.415(6) . ?
C5 H5 0.9300 . ?
C18 H18 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
_geom_angle_publ_flag
C8 N2 C3 121.9(2) . . ?
C8 N2 C4 120.4(3) . . ?
C4 N2 C3 117.8(3) . . ?
C8 N1 C1 116.9(2) . . ?
N3 C15 C12 178.8(4) . . ?
N2 C8 C7 118.7(3) . . ?
N1 C8 N2 122.8(3) . . ?
N1 C8 C7 118.5(3) . . ?
N1 C1 C2 124.6(3) . . ?
N1 C1 C9 112.6(2) . . ?
C2 C1 C9 122.8(2) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 C16 123.0(2) . . ?
C3 C2 C16 118.3(2) . . ?
C2 C3 N2 114.9(2) . . ?
O1 C3 N2 116.3(3) . . ?
O1 C3 C2 128.8(3) . . ?
C14 C9 C1 120.9(2) . . ?
C10 C9 C1 120.2(3) . . ?
C10 C9 C14 118.7(3) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C21 C16 C2 121.5(3) . . ?
C21 C16 C17 118.5(3) . . ?
C17 C16 C2 119.9(3) . . ?
C13 C12 C15 119.6(3) . . ?
C13 C12 C11 121.2(3) . . ?
C11 C12 C15 119.1(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C16 C21 H21 119.8 . . ?
C16 C21 C20 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.2 . . ?
N2 C4 H4 120.1 . . ?
C5 C4 N2 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C20 C19 Cl1 121.8(3) . . ?
C18 C19 Cl1 117.2(3) . . ?
C18 C19 C20 121.0(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119.1 . . ?
C7 C6 H6 121.1 . . ?
C7 C6 C5 117.8(3) . . ?
C5 C6 H6 121.1 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.6 . . ?

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
Cl1 C19 C18 C17 -179.8(3) . . . . ?
N2 C8 C7 C6 -0.7(5) . . . . ?
N2 C4 C5 C6 1.4(6) . . . . ?
N1 C8 C7 C6 -179.5(3) . . . . ?
N1 C1 C2 C3 6.7(4) . . . . ?
N1 C1 C2 C16 -170.5(3) . . . . ?
N1 C1 C9 C14 -120.7(3) . . . . ?
N1 C1 C9 C10 54.7(4) . . . . ?
C15 C12 C11 C10 178.9(3) . . . . ?
C8 N2 C3 C2 1.8(4) . . . . ?
C8 N2 C3 O1 -178.1(3) . . . . ?
C8 N2 C4 C5 -2.3(5) . . . . ?
C8 N1 C1 C2 -2.5(4) . . . . ?
C8 N1 C1 C9 175.2(2) . . . . ?
C8 C7 C6 C5 -0.2(5) . . . . ?
C1 N1 C8 N2 -2.1(4) . . . . ?
C1 N1 C8 C7 176.7(3) . . . . ?
C1 C2 C3 N2 -6.0(4) . . . . ?
C1 C2 C3 O1 174.0(3) . . . . ?
C1 C2 C16 C21 -144.5(3) . . . . ?
C1 C2 C16 C17 39.8(4) . . . . ?
C1 C9 C14 C13 175.2(3) . . . . ?
C1 C9 C10 C11 -176.4(3) . . . . ?
C2 C1 C9 C14 57.1(4) . . . . ?
C2 C1 C9 C10 -127.6(3) . . . . ?
C2 C16 C21 C20 -179.9(3) . . . . ?
C2 C16 C17 C18 179.4(3) . . . . ?
C3 N2 C8 N1 2.4(4) . . . . ?
C3 N2 C8 C7 -176.4(3) . . . . ?
C3 N2 C4 C5 176.1(3) . . . . ?
C3 C2 C16 C21 38.2(4) . . . . ?
C3 C2 C16 C17 -137.5(3) . . . . ?
C9 C1 C2 C3 -170.7(3) . . . . ?
C9 C1 C2 C16 12.0(4) . . . . ?
C9 C14 C13 C12 0.9(4) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C14 C13 C12 C15 180.0(3) . . . . ?
C14 C13 C12 C11 -0.4(5) . . . . ?
C13 C12 C11 C10 -0.8(5) . . . . ?
C16 C2 C3 N2 171.4(2) . . . . ?
C16 C2 C3 O1 -8.6(5) . . . . ?
C16 C21 C20 C19 1.8(5) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C21 C16 C17 C18 3.6(5) . . . . ?
C21 C20 C19 Cl1 179.1(2) . . . . ?
C21 C20 C19 C18 1.3(5) . . . . ?
C7 C6 C5 C4 -0.1(6) . . . . ?
C20 C19 C18 C17 -1.9(5) . . . . ?
C4 N2 C8 N1 -179.3(3) . . . . ?
C4 N2 C8 C7 1.9(4) . . . . ?
C4 N2 C3 C2 -176.5(3) . . . . ?
C4 N2 C3 O1 3.5(4) . . . . ?
C17 C16 C21 C20 -4.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/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_dv_1_rt
_database_code_depnum_ccdc_archive 'CCDC 1505625'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
4-(3-(4-chlorophenyl)-4-imino-4H-pyrido[1,2-a]pyrimidin-2-yl)benzonitrile
_chemical_formula_moiety         C21H13ClN4
_chemical_formula_weight         356.80
_chemical_melting_point          >473
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5726(15)
_cell_length_b                   21.214(2)
_cell_length_c                   8.2058(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.624(5)
_cell_angle_gamma                90
_cell_volume                     1744.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10786
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.920
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
scan:
	Number of images: 434
	           Slice: -37.0000 - 93.2000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 334
	           Slice: -45.0000 - 55.2000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 334
	           Slice: -45.0000 - 55.2000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.017644
_diffrn_orient_matrix_UB_12      0.122686
_diffrn_orient_matrix_UB_13      -0.034270
_diffrn_orient_matrix_UB_21      0.035261
_diffrn_orient_matrix_UB_22      0.013017
_diffrn_orient_matrix_UB_23      0.028446
_diffrn_orient_matrix_UB_31      0.057041
_diffrn_orient_matrix_UB_32      0.019386
_diffrn_orient_matrix_UB_33      -0.079579
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2456
_reflns_number_total             3959
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1264P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.2182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C12(H12), C17(H17), C9(H9), C20(H20), C6(H6), C10(H10),
 C19(H19), C3(H3A), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20802(9) 0.30583(4) 1.01332(10) 0.0854(3) Uani 1 1 d . . . . .
N1 N 0.39381(19) 0.46457(9) 0.2063(2) 0.0491(5) Uani 1 1 d . . . . .
N2 N 0.19057(19) 0.51737(9) 0.1804(2) 0.0490(5) Uani 1 1 d . . . . .
N3 N 0.0753(3) 0.50378(12) 0.3730(3) 0.0765(8) Uani 1 1 d . . . . .
H3 H 0.076(3) 0.4828(16) 0.462(4) 0.092 Uiso 1 1 d R . . . .
C1 C 0.3745(2) 0.42908(10) 0.3360(3) 0.0455(5) Uani 1 1 d . . . . .
C2 C 0.2696(2) 0.43719(10) 0.3968(3) 0.0454(5) Uani 1 1 d . . . . .
C15 C 0.2543(2) 0.40368(10) 0.5484(3) 0.0474(6) Uani 1 1 d . . . . .
C8 C 0.4820(2) 0.38214(11) 0.4122(3) 0.0466(5) Uani 1 1 d . . . . .
C13 C 0.6148(2) 0.39963(11) 0.4445(3) 0.0515(6) Uani 1 1 d . . . . .
H13 H 0.6346 0.4389 0.4085 0.062 Uiso 1 1 calc R . . . .
C7 C 0.3019(2) 0.50658(11) 0.1306(3) 0.0479(6) Uani 1 1 d . . . . .
C11 C 0.6881(2) 0.30053(11) 0.5799(3) 0.0548(6) Uani 1 1 d . . . . .
C00C C 0.1716(2) 0.48520(11) 0.3244(3) 0.0512(6) Uani 1 1 d . . . . .
C16 C 0.1462(2) 0.36451(12) 0.5337(3) 0.0547(6) Uani 1 1 d . . . . .
H16 H 0.0827 0.3584 0.4265 0.066 Uiso 1 1 calc R . . . .
N4 N 0.8760(3) 0.22795(12) 0.7603(4) 0.0884(9) Uani 1 1 d . . . . .
C12 C 0.7172(2) 0.35956(12) 0.5289(3) 0.0555(6) Uani 1 1 d . . . . .
H12 H 0.8055 0.3720 0.5515 0.067 Uiso 1 1 calc R . . . .
C17 C 0.1312(3) 0.33443(12) 0.6760(3) 0.0578(6) Uani 1 1 d . . . . .
H17 H 0.0579 0.3086 0.6650 0.069 Uiso 1 1 calc R . . . .
C9 C 0.4546(2) 0.32182(11) 0.4572(3) 0.0581(6) Uani 1 1 d . . . . .
H9 H 0.3664 0.3087 0.4307 0.070 Uiso 1 1 calc R . . . .
C14 C 0.7938(3) 0.26010(12) 0.6796(4) 0.0632(7) Uani 1 1 d . . . . .
C20 C 0.3485(3) 0.41115(11) 0.7091(3) 0.0566(6) Uani 1 1 d . . . . .
H20 H 0.4221 0.4370 0.7212 0.068 Uiso 1 1 calc R . . . .
C6 C 0.3148(3) 0.54244(12) -0.0092(3) 0.0593(7) Uani 1 1 d . . . . .
H6 H 0.3879 0.5359 -0.0468 0.071 Uiso 1 1 calc R . . . .
C10 C 0.5561(3) 0.28125(12) 0.5405(4) 0.0631(7) Uani 1 1 d . . . . .
H10 H 0.5365 0.2410 0.5704 0.076 Uiso 1 1 calc R . . . .
C18 C 0.2258(3) 0.34316(11) 0.8331(3) 0.0560(6) Uani 1 1 d . . . . .
C19 C 0.3351(3) 0.38089(12) 0.8519(3) 0.0595(7) Uani 1 1 d . . . . .
H19 H 0.3991 0.3860 0.9592 0.071 Uiso 1 1 calc R . . . .
C3 C 0.0969(3) 0.56267(13) 0.0980(3) 0.0612(7) Uani 1 1 d . . . . .
H3A H 0.0232 0.5696 0.1341 0.073 Uiso 1 1 calc R . . . .
C4 C 0.1114(3) 0.59641(13) -0.0323(3) 0.0679(8) Uani 1 1 d . . . . .
H4 H 0.0483 0.6268 -0.0857 0.081 Uiso 1 1 calc R . . . .
C5 C 0.2221(3) 0.58609(14) -0.0886(3) 0.0703(8) Uani 1 1 d . . . . .
H5 H 0.2317 0.6092 -0.1803 0.084 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 1.740(3) . ?
N1 C1 1.371(3) . ?
N1 C7 1.319(3) . ?
N2 C7 1.383(3) . ?
N2 C00C 1.433(3) . ?
N2 C3 1.391(3) . ?
N3 H3 0.85(3) . ?
N3 C00C 1.269(3) . ?
C1 C2 1.364(3) . ?
C1 C8 1.490(3) . ?
C2 C15 1.486(3) . ?
C2 C00C 1.439(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.385(3) . ?
C8 C13 1.393(3) . ?
C8 C9 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(3) . ?
C7 C6 1.418(3) . ?
C11 C12 1.386(3) . ?
C11 C14 1.439(3) . ?
C11 C10 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
N4 C14 1.136(3) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.369(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.354(4) . ?
C10 H10 0.9300 . ?
C18 C19 1.373(4) . ?
C19 H19 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.335(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(4) . ?
C5 H5 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
_geom_angle_publ_flag
C7 N1 C1 117.8(2) . . ?
C7 N2 C00C 121.44(19) . . ?
C7 N2 C3 120.8(2) . . ?
C3 N2 C00C 117.7(2) . . ?
C00C N3 H3 109(2) . . ?
N1 C1 C8 114.2(2) . . ?
C2 C1 N1 123.7(2) . . ?
C2 C1 C8 122.1(2) . . ?
C1 C2 C15 124.3(2) . . ?
C1 C2 C00C 120.0(2) . . ?
C00C C2 C15 115.3(2) . . ?
C16 C15 C2 121.4(2) . . ?
C20 C15 C2 120.3(2) . . ?
C20 C15 C16 118.3(2) . . ?
C13 C8 C1 119.3(2) . . ?
C9 C8 C1 122.1(2) . . ?
C9 C8 C13 118.6(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
N1 C7 N2 122.8(2) . . ?
N1 C7 C6 119.8(2) . . ?
N2 C7 C6 117.5(2) . . ?
C12 C11 C14 120.2(2) . . ?
C12 C11 C10 119.9(2) . . ?
C10 C11 C14 119.8(2) . . ?
N2 C00C C2 113.9(2) . . ?
N3 C00C N2 116.7(2) . . ?
N3 C00C C2 129.4(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.4 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
N4 C14 C11 178.7(3) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.1(2) . . ?
C19 C20 H20 119.4 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C17 C18 Cl1 119.6(2) . . ?
C17 C18 C19 121.3(2) . . ?
C19 C18 Cl1 119.0(2) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.5 . . ?
N2 C3 H3A 119.5 . . ?
C4 C3 N2 120.9(3) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 -179.3(2) . . . . ?
N1 C1 C2 C15 -173.60(19) . . . . ?
N1 C1 C2 C00C -0.1(3) . . . . ?
N1 C1 C8 C13 42.1(3) . . . . ?
N1 C1 C8 C9 -139.8(2) . . . . ?
N1 C7 C6 C5 -179.7(2) . . . . ?
N2 C7 C6 C5 0.9(4) . . . . ?
N2 C3 C4 C5 0.4(4) . . . . ?
C1 N1 C7 N2 2.1(3) . . . . ?
C1 N1 C7 C6 -177.3(2) . . . . ?
C1 C2 C15 C16 -119.1(3) . . . . ?
C1 C2 C15 C20 61.1(3) . . . . ?
C1 C2 C00C N2 4.9(3) . . . . ?
C1 C2 C00C N3 -172.7(3) . . . . ?
C1 C8 C13 C12 174.1(2) . . . . ?
C1 C8 C9 C10 -174.5(2) . . . . ?
C2 C1 C8 C13 -135.3(2) . . . . ?
C2 C1 C8 C9 42.8(3) . . . . ?
C2 C15 C16 C17 -178.7(2) . . . . ?
C2 C15 C20 C19 179.3(2) . . . . ?
C15 C2 C00C N2 178.92(18) . . . . ?
C15 C2 C00C N3 1.3(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C15 C20 C19 C18 -0.3(4) . . . . ?
C8 C1 C2 C15 3.6(3) . . . . ?
C8 C1 C2 C00C 177.0(2) . . . . ?
C8 C13 C12 C11 1.1(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C13 C8 C9 C10 3.6(4) . . . . ?
C7 N1 C1 C2 -3.6(3) . . . . ?
C7 N1 C1 C8 179.04(18) . . . . ?
C7 N2 C00C N3 171.6(2) . . . . ?
C7 N2 C00C C2 -6.3(3) . . . . ?
C7 N2 C3 C4 0.7(4) . . . . ?
C7 C6 C5 C4 0.2(4) . . . . ?
C00C N2 C7 N1 3.0(3) . . . . ?
C00C N2 C7 C6 -177.5(2) . . . . ?
C00C N2 C3 C4 177.1(2) . . . . ?
C00C C2 C15 C16 67.2(3) . . . . ?
C00C C2 C15 C20 -112.6(3) . . . . ?
C16 C15 C20 C19 -0.6(4) . . . . ?
C16 C17 C18 Cl1 179.79(19) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C12 C11 C10 C9 -2.7(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C9 C8 C13 C12 -4.0(4) . . . . ?
C14 C11 C12 C13 -175.3(2) . . . . ?
C14 C11 C10 C9 174.8(3) . . . . ?
C20 C15 C16 C17 1.1(4) . . . . ?
C10 C11 C12 C13 2.3(4) . . . . ?
C3 N2 C7 N1 179.3(2) . . . . ?
C3 N2 C7 C6 -1.3(3) . . . . ?
C3 N2 C00C N3 -4.8(3) . . . . ?
C3 N2 C00C C2 177.3(2) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/ACETONITRILE'
