# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mx3243
_database_code_depnum_ccdc_archive 'CCDC 1418031'
_audit_update_record             
;
2015-08-11 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
_audit_creation_date             2014-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '4-anilinoquinazoline derivative'
_chemical_formula_moiety         'C20 H17 Cl F N5 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H21 Cl F N5 O4'
_chemical_formula_weight         449.87
_chemical_melting_point          358-362
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'
F F 0.0171 0.0103 '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_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.369(2)
_cell_length_b                   10.914(3)
_cell_length_c                   14.365(5)
_cell_angle_alpha                69.058(11)
_cell_angle_beta                 83.580(15)
_cell_angle_gamma                72.354(11)
_cell_volume                     1028.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3297
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4808
_cell_measurement_theta_min      2.9007
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8802
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4647
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0162
_diffrn_orient_matrix_UB_12      0.1290
_diffrn_orient_matrix_UB_13      -0.0582
_diffrn_orient_matrix_UB_21      0.0614
_diffrn_orient_matrix_UB_22      -0.0632
_diffrn_orient_matrix_UB_23      -0.0520
_diffrn_orient_matrix_UB_31      -0.0693
_diffrn_orient_matrix_UB_32      -0.0038
_diffrn_orient_matrix_UB_33      -0.0271
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4119
_reflns_number_total             4645
_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 (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'

;
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.100
_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)+(0.0723P)²+0.5076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1560
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C11(H11), C13(H13), C16(H16), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.96014(10) 0.85461(6) 0.04825(4) 0.0489(2) Uani 1 1 d . . . . .
F1 F 1.1580(2) 0.61073(14) -0.00228(9) 0.0465(4) Uani 1 1 d . . . . .
O1 O 0.7453(2) 0.17544(14) 0.74414(10) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.5396(2) 0.33954(16) 0.83006(11) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.4249(3) -0.1276(2) 0.76453(15) 0.0418(5) Uani 1 1 d . . . . .
N2 N 0.6879(3) -0.08740(18) 0.79212(13) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.5422(2) 0.73151(17) 0.53632(13) 0.0321(4) Uani 1 1 d . . . . .
N4 N 0.7248(2) 0.70050(17) 0.39390(13) 0.0312(4) Uani 1 1 d . . . . .
N5 N 0.8843(2) 0.48618(17) 0.38569(12) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.5688(4) -0.0802(3) 0.8719(2) 0.0528(7) Uani 1 1 d . . . . .
H1 H 0.5925 -0.0619 0.9271 0.063 Uiso 1 1 calc R . . . .
C2 C 0.4100(4) -0.1052(3) 0.8535(2) 0.0551(7) Uani 1 1 d . . . . .
H2 H 0.3046 -0.1069 0.8955 0.066 Uiso 1 1 calc R . . . .
C3 C 0.5957(3) -0.1163(2) 0.73069(16) 0.0350(5) Uani 1 1 d . . . . .
H3 H 0.6463 -0.1273 0.6709 0.042 Uiso 1 1 calc R . . . .
C4 C 0.8744(3) -0.0611(2) 0.77466(16) 0.0344(5) Uani 1 1 d . . . . .
H4A H 0.9618 -0.1289 0.7496 0.041 Uiso 1 1 calc R . . . .
H4B H 0.9241 -0.0705 0.8374 0.041 Uiso 1 1 calc R . . . .
C5 C 0.8641(3) 0.0798(2) 0.70112(15) 0.0328(4) Uani 1 1 d . . . . .
H5A H 0.9903 0.0927 0.6884 0.039 Uiso 1 1 calc R . . . .
H5B H 0.8111 0.0920 0.6385 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7026(3) 0.30998(19) 0.68635(14) 0.0265(4) Uani 1 1 d . . . . .
C7 C 0.5854(3) 0.4018(2) 0.73402(14) 0.0279(4) Uani 1 1 d . . . . .
C8 C 0.5331(3) 0.5393(2) 0.68317(15) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.4553 0.5986 0.7139 0.034 Uiso 1 1 calc R . . . .
C9 C 0.5962(3) 0.5922(2) 0.58434(14) 0.0261(4) Uani 1 1 d . . . . .
C10 C 0.7139(2) 0.50206(19) 0.53749(14) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.7658(3) 0.35973(19) 0.59035(14) 0.0260(4) Uani 1 1 d . . . . .
H11 H 0.8429 0.2996 0.5601 0.031 Uiso 1 1 calc R . . . .
C12 C 0.4307(3) 0.4261(3) 0.88318(16) 0.0388(5) Uani 1 1 d . . . . .
H12A H 0.3090 0.4755 0.8518 0.058 Uiso 1 1 calc GR . . . .
H12B H 0.4971 0.4896 0.8827 0.058 Uiso 1 1 calc GR . . . .
H12C H 0.4126 0.3714 0.9508 0.058 Uiso 1 1 calc GR . . . .
C13 C 0.6114(3) 0.7750(2) 0.44620(16) 0.0340(5) Uani 1 1 d . . . . .
H13 H 0.5776 0.8694 0.4144 0.041 Uiso 1 1 calc R . . . .
C14 C 0.7737(3) 0.56550(19) 0.43746(14) 0.0249(4) Uani 1 1 d . . . . .
C15 C 0.9489(3) 0.5262(2) 0.28598(14) 0.0260(4) Uani 1 1 d . . . . .
C16 C 0.9194(3) 0.6609(2) 0.22240(15) 0.0295(4) Uani 1 1 d . . . . .
H16 H 0.8519 0.7328 0.2442 0.035 Uiso 1 1 calc R . . . .
C17 C 0.9920(3) 0.6869(2) 0.12598(15) 0.0323(4) Uani 1 1 d . . . . .
C18 C 1.0898(3) 0.5816(2) 0.09244(15) 0.0336(5) Uani 1 1 d . . . . .
C19 C 1.1207(3) 0.4485(2) 0.15399(16) 0.0364(5) Uani 1 1 d . . . . .
H19 H 1.1876 0.3776 0.1311 0.044 Uiso 1 1 calc R . . . .
C20 C 1.0512(3) 0.4204(2) 0.25087(15) 0.0321(4) Uani 1 1 d . . . . .
H20 H 1.0729 0.3301 0.2931 0.039 Uiso 1 1 calc R . . . .
O4 O 1.0460(3) 0.16958(17) 0.45334(13) 0.0368(4) Uani 1 1 d . . . . .
O3 O 0.7578(2) 0.08742(15) 0.40730(12) 0.0375(4) Uani 1 1 d . . . . .
H3A H 0.7259 0.0988 0.3512 0.056 Uiso 1 1 d R . . . .
H3B H 0.6693 0.1397 0.4264 0.056 Uiso 1 1 d R . . . .
H5 H 0.919(4) 0.402(3) 0.4141(19) 0.038(7) Uiso 1 1 d . . . . .
H4C H 0.961(5) 0.142(3) 0.437(2) 0.060(9) Uiso 1 1 d . . . . .
H4D H 1.110(5) 0.103(3) 0.493(2) 0.059(9) 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 C17 1.729(2) . ?
F1 C18 1.356(2) . ?
O1 C5 1.423(2) . ?
O1 C6 1.361(2) . ?
O2 C7 1.358(2) . ?
O2 C12 1.428(2) . ?
N1 C2 1.371(3) . ?
N1 C3 1.322(3) . ?
N2 C1 1.374(3) . ?
N2 C3 1.343(3) . ?
N2 C4 1.464(3) . ?
N3 C9 1.375(3) . ?
N3 C13 1.312(3) . ?
N4 C13 1.345(3) . ?
N4 C14 1.327(3) . ?
N5 C14 1.365(2) . ?
N5 C15 1.412(2) . ?
C1 C2 1.352(4) . ?
C4 C5 1.508(3) . ?
C6 C7 1.433(3) . ?
C6 C11 1.374(3) . ?
C7 C8 1.365(3) . ?
C8 C9 1.412(3) . ?
C9 C10 1.414(3) . ?
C10 C11 1.413(3) . ?
C10 C14 1.439(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.400(3) . ?
C16 C17 1.389(3) . ?
C17 C18 1.374(3) . ?
C18 C19 1.368(3) . ?
C19 C20 1.387(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
C6 O1 C5 117.02(15) . . ?
C7 O2 C12 116.95(17) . . ?
C3 N1 C2 104.1(2) . . ?
C1 N2 C4 126.8(2) . . ?
C3 N2 C1 106.55(19) . . ?
C3 N2 C4 126.61(18) . . ?
C13 N3 C9 115.88(17) . . ?
C14 N4 C13 116.96(17) . . ?
C14 N5 C15 129.03(17) . . ?
C2 C1 N2 105.8(2) . . ?
C1 C2 N1 111.0(2) . . ?
N1 C3 N2 112.57(19) . . ?
N2 C4 C5 112.08(17) . . ?
O1 C5 C4 107.08(16) . . ?
O1 C6 C7 114.62(17) . . ?
O1 C6 C11 124.98(17) . . ?
C11 C6 C7 120.38(18) . . ?
O2 C7 C6 114.28(17) . . ?
O2 C7 C8 125.87(17) . . ?
C8 C7 C6 119.84(17) . . ?
C7 C8 C9 120.55(17) . . ?
N3 C9 C8 118.65(17) . . ?
N3 C9 C10 121.58(17) . . ?
C8 C9 C10 119.77(17) . . ?
C9 C10 C14 115.79(17) . . ?
C11 C10 C9 119.30(17) . . ?
C11 C10 C14 124.90(17) . . ?
C6 C11 C10 120.15(17) . . ?
N3 C13 N4 128.26(19) . . ?
N4 C14 N5 118.71(17) . . ?
N4 C14 C10 121.46(17) . . ?
N5 C14 C10 119.82(17) . . ?
C16 C15 N5 124.85(17) . . ?
C16 C15 C20 118.91(18) . . ?
C20 C15 N5 116.24(17) . . ?
C17 C16 C15 119.29(18) . . ?
C16 C17 Cl1 119.08(16) . . ?
C18 C17 Cl1 119.97(16) . . ?
C18 C17 C16 120.95(19) . . ?
F1 C18 C17 119.39(19) . . ?
F1 C18 C19 120.01(19) . . ?
C19 C18 C17 120.60(19) . . ?
C18 C19 C20 119.32(19) . . ?
C19 C20 C15 120.92(19) . . ?

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 C17 C18 F1 -1.0(3) . . . . ?
Cl1 C17 C18 C19 178.15(18) . . . . ?
F1 C18 C19 C20 179.54(19) . . . . ?
O1 C6 C7 O2 1.5(2) . . . . ?
O1 C6 C7 C8 -179.89(17) . . . . ?
O1 C6 C11 C10 -179.38(17) . . . . ?
O2 C7 C8 C9 177.44(18) . . . . ?
N2 C1 C2 N1 -0.2(3) . . . . ?
N2 C4 C5 O1 62.9(2) . . . . ?
N3 C9 C10 C11 179.74(17) . . . . ?
N3 C9 C10 C14 0.4(3) . . . . ?
N5 C15 C16 C17 179.37(18) . . . . ?
N5 C15 C20 C19 179.87(19) . . . . ?
C1 N2 C3 N1 0.4(3) . . . . ?
C1 N2 C4 C5 -100.2(3) . . . . ?
C2 N1 C3 N2 -0.5(3) . . . . ?
C3 N1 C2 C1 0.4(3) . . . . ?
C3 N2 C1 C2 -0.1(3) . . . . ?
C3 N2 C4 C5 76.0(3) . . . . ?
C4 N2 C1 C2 176.7(2) . . . . ?
C4 N2 C3 N1 -176.48(19) . . . . ?
C5 O1 C6 C7 -178.95(17) . . . . ?
C5 O1 C6 C11 -0.1(3) . . . . ?
C6 O1 C5 C4 -174.44(17) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C6 C11 C10 -0.6(3) . . . . ?
C7 C8 C9 N3 -179.15(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C14 -178.94(17) . . . . ?
C9 N3 C13 N4 1.7(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C10 C14 N4 1.8(3) . . . . ?
C9 C10 C14 N5 -178.59(16) . . . . ?
C11 C6 C7 O2 -177.40(17) . . . . ?
C11 C6 C7 C8 1.2(3) . . . . ?
C11 C10 C14 N4 -177.48(18) . . . . ?
C11 C10 C14 N5 2.1(3) . . . . ?
C12 O2 C7 C6 177.04(17) . . . . ?
C12 O2 C7 C8 -1.5(3) . . . . ?
C13 N3 C9 C8 177.34(18) . . . . ?
C13 N3 C9 C10 -2.0(3) . . . . ?
C13 N4 C14 N5 178.17(17) . . . . ?
C13 N4 C14 C10 -2.2(3) . . . . ?
C14 N4 C13 N3 0.5(3) . . . . ?
C14 N5 C15 C16 4.6(3) . . . . ?
C14 N5 C15 C20 -176.02(19) . . . . ?
C14 C10 C11 C6 179.10(17) . . . . ?
C15 N5 C14 N4 -4.5(3) . . . . ?
C15 N5 C14 C10 175.90(17) . . . . ?
C15 C16 C17 Cl1 -178.36(15) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C16 C17 C18 F1 179.74(19) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?

####################################################################### 
# 
# 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_sa408
_database_code_depnum_ccdc_archive 'CCDC 1418032'
_audit_update_record             
;
2015-08-11 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'cyclometalated platinum'
_chemical_name_common            ?
_chemical_melting_point          631-635
_chemical_formula_moiety         '2(C20 H13 Cl N2 Pt), C H2 Cl2'
_chemical_formula_sum            'C41 H28 Cl4 N4 Pt2'
_chemical_formula_weight         1108.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/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'
'-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                   19.794(5)
_cell_length_b                   7.7967(18)
_cell_length_c                   23.287(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.577(4)
_cell_angle_gamma                90.00
_cell_volume                     3444.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    648
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2104
_exptl_absorpt_coefficient_mu    8.463
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7853
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13531
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3894
_reflns_number_gt                3496
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (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)+(0.0410P)²+32.9050P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3894
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
Pt1 Pt 0.195008(17) 0.46217(4) 0.452183(14) 0.02863(13) Uani 1 1 d . . .
Cl1 Cl 0.08947(12) 0.4222(3) 0.37955(10) 0.0400(5) Uani 1 1 d . . .
Cl2 Cl 0.06748(17) 0.0472(4) 0.23692(13) 0.0601(8) Uani 1 1 d . . .
H21 H 0.0272 0.2454 0.2850 0.072 Uiso 1 1 d R . .
N1 N 0.2830(4) 0.5046(8) 0.5147(3) 0.0307(16) Uani 1 1 d . . .
N2 N 0.1561(4) 0.5802(9) 0.5178(3) 0.0310(16) Uani 1 1 d . . .
C1 C 0.3870(5) 0.3130(11) 0.4246(4) 0.037(2) Uani 1 1 d . . .
H1A H 0.4345 0.3236 0.4487 0.044 Uiso 1 1 calc R . .
C3 C 0.4263(5) 0.1689(12) 0.3447(5) 0.043(2) Uani 1 1 d . . .
H3A H 0.4741 0.1757 0.3681 0.051 Uiso 1 1 calc R . .
C2 C 0.3719(4) 0.2337(10) 0.3674(4) 0.034(2) Uani 1 1 d . . .
C4 C 0.4093(6) 0.0969(13) 0.2892(5) 0.048(3) Uani 1 1 d . . .
H4A H 0.4461 0.0561 0.2740 0.058 Uiso 1 1 calc R . .
C5 C 0.3393(6) 0.0813(13) 0.2538(5) 0.049(3) Uani 1 1 d . . .
H5A H 0.3289 0.0324 0.2149 0.059 Uiso 1 1 calc R . .
C6 C 0.2861(5) 0.1368(12) 0.2757(4) 0.039(2) Uani 1 1 d . . .
H6A H 0.2386 0.1229 0.2521 0.046 Uiso 1 1 calc R . .
C7 C 0.3002(5) 0.2147(11) 0.3328(4) 0.0339(19) Uani 1 1 d . . .
C8 C 0.2458(5) 0.2760(10) 0.3556(4) 0.0310(18) Uani 1 1 d . . .
H8A H 0.1981 0.2598 0.3328 0.037 Uiso 1 1 calc R . .
C9 C 0.2603(4) 0.3592(10) 0.4103(4) 0.0301(18) Uani 1 1 d . . .
C10 C 0.3321(4) 0.3756(11) 0.4457(4) 0.0305(18) Uani 1 1 d . . .
C11 C 0.3443(5) 0.4582(10) 0.5034(4) 0.0318(19) Uani 1 1 d . . .
C12 C 0.4064(5) 0.4897(12) 0.5474(4) 0.040(2) Uani 1 1 d . . .
H12A H 0.4502 0.4587 0.5411 0.048 Uiso 1 1 calc R . .
C13 C 0.4054(5) 0.5664(11) 0.6009(4) 0.038(2) Uani 1 1 d . . .
H13A H 0.4483 0.5839 0.6315 0.045 Uiso 1 1 calc R . .
C14 C 0.3426(5) 0.6173(11) 0.6100(4) 0.039(2) Uani 1 1 d . . .
H14A H 0.3418 0.6754 0.6457 0.047 Uiso 1 1 calc R . .
C15 C 0.2807(5) 0.5818(11) 0.5659(4) 0.0323(19) Uani 1 1 d . . .
C16 C 0.2082(6) 0.6241(11) 0.5674(4) 0.040(2) Uani 1 1 d . . .
C17 C 0.1927(6) 0.7004(12) 0.6164(4) 0.044(2) Uani 1 1 d . . .
H17A H 0.2297 0.7315 0.6508 0.053 Uiso 1 1 calc R . .
C18 C 0.1234(6) 0.7305(13) 0.6147(5) 0.049(3) Uani 1 1 d . . .
H18A H 0.1124 0.7842 0.6476 0.058 Uiso 1 1 calc R . .
C19 C 0.0703(6) 0.6814(13) 0.5646(4) 0.046(2) Uani 1 1 d . . .
H19A H 0.0223 0.6962 0.5633 0.055 Uiso 1 1 calc R . .
C20 C 0.0881(5) 0.6102(12) 0.5162(4) 0.040(2) Uani 1 1 d . . .
H20A H 0.0516 0.5819 0.4810 0.048 Uiso 1 1 calc R . .
C21 C 0.0000 0.1782(18) 0.2500 0.052(4) Uani 1 2 d S . .


_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
Pt1 N1 1.953(8) . ?
Pt1 C9 1.995(8) . ?
Pt1 N2 2.110(7) . ?
Pt1 Cl1 2.303(2) . ?
Cl2 C21 1.775(9) . ?
N1 C15 1.349(11) . ?
N1 C11 1.362(12) . ?
N2 C16 1.354(12) . ?
N2 C20 1.356(11) . ?
C1 C10 1.402(12) . ?
C1 C2 1.422(12) . ?
C1 H1A 0.9500 . ?
C3 C4 1.361(14) . ?
C3 C2 1.420(12) . ?
C3 H3A 0.9500 . ?
C2 C7 1.425(12) . ?
C4 C5 1.402(15) . ?
C4 H4A 0.9500 . ?
C5 C6 1.365(13) . ?
C5 H5A 0.9500 . ?
C6 C7 1.416(12) . ?
C6 H6A 0.9500 . ?
C7 C8 1.413(12) . ?
C8 C9 1.386(11) . ?
C8 H8A 0.9500 . ?
C9 C10 1.430(11) . ?
C10 C11 1.448(12) . ?
C11 C12 1.379(12) . ?
C12 C13 1.387(14) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(14) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(12) . ?
C14 H14A 0.9500 . ?
C15 C16 1.483(13) . ?
C16 C17 1.397(12) . ?
C17 C18 1.381(14) . ?
C17 H17A 0.9500 . ?
C18 C19 1.383(15) . ?
C18 H18A 0.9500 . ?
C19 C20 1.389(13) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 Cl2 1.775(9) 2 ?
C21 H21 0.9892 . ?

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
N1 Pt1 C9 82.4(3) . . ?
N1 Pt1 N2 79.6(3) . . ?
C9 Pt1 N2 161.9(3) . . ?
N1 Pt1 Cl1 177.7(2) . . ?
C9 Pt1 Cl1 99.5(3) . . ?
N2 Pt1 Cl1 98.5(2) . . ?
C15 N1 C11 123.0(8) . . ?
C15 N1 Pt1 119.1(6) . . ?
C11 N1 Pt1 117.8(6) . . ?
C16 N2 C20 119.3(8) . . ?
C16 N2 Pt1 112.4(6) . . ?
C20 N2 Pt1 128.3(6) . . ?
C10 C1 C2 120.1(8) . . ?
C10 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C4 C3 C2 119.5(10) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C2 C1 121.6(9) . . ?
C3 C2 C7 119.4(9) . . ?
C1 C2 C7 119.0(8) . . ?
C3 C4 C5 121.9(9) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 119.4(10) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 121.4(9) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C8 C7 C6 122.0(8) . . ?
C8 C7 C2 119.7(8) . . ?
C6 C7 C2 118.3(8) . . ?
C9 C8 C7 121.6(8) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 118.8(8) . . ?
C8 C9 Pt1 130.1(7) . . ?
C10 C9 Pt1 111.0(6) . . ?
C1 C10 C9 120.7(8) . . ?
C1 C10 C11 122.5(8) . . ?
C9 C10 C11 116.8(8) . . ?
N1 C11 C12 117.7(8) . . ?
N1 C11 C10 111.9(8) . . ?
C12 C11 C10 130.3(9) . . ?
C11 C12 C13 120.3(9) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 120.5(9) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 118.4(8) . . ?
C13 C14 H14A 120.8 . . ?
C15 C14 H14A 120.8 . . ?
N1 C15 C14 120.0(8) . . ?
N1 C15 C16 113.4(8) . . ?
C14 C15 C16 126.6(8) . . ?
N2 C16 C17 120.9(9) . . ?
N2 C16 C15 115.5(8) . . ?
C17 C16 C15 123.6(9) . . ?
C18 C17 C16 119.8(10) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C17 C18 C19 119.1(9) . . ?
C17 C18 H18A 120.5 . . ?
C19 C18 H18A 120.5 . . ?
C18 C19 C20 119.2(9) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
N2 C20 C19 121.7(9) . . ?
N2 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
Cl2 C21 Cl2 109.8(8) 2 . ?
Cl2 C21 H21 115.0 2 . ?
Cl2 C21 H21 100.7 . . ?

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
C9 Pt1 N1 C15 -179.2(7) . . . . ?
N2 Pt1 N1 C15 -0.2(6) . . . . ?
Cl1 Pt1 N1 C15 35(6) . . . . ?
C9 Pt1 N1 C11 2.5(6) . . . . ?
N2 Pt1 N1 C11 -178.6(6) . . . . ?
Cl1 Pt1 N1 C11 -144(5) . . . . ?
N1 Pt1 N2 C16 0.1(6) . . . . ?
C9 Pt1 N2 C16 3.4(12) . . . . ?
Cl1 Pt1 N2 C16 -178.6(6) . . . . ?
N1 Pt1 N2 C20 -177.9(8) . . . . ?
C9 Pt1 N2 C20 -174.6(9) . . . . ?
Cl1 Pt1 N2 C20 3.5(7) . . . . ?
C4 C3 C2 C1 -178.8(9) . . . . ?
C4 C3 C2 C7 3.1(13) . . . . ?
C10 C1 C2 C3 -180.0(8) . . . . ?
C10 C1 C2 C7 -1.8(12) . . . . ?
C2 C3 C4 C5 -1.4(15) . . . . ?
C3 C4 C5 C6 -1.2(16) . . . . ?
C4 C5 C6 C7 1.9(15) . . . . ?
C5 C6 C7 C8 178.7(9) . . . . ?
C5 C6 C7 C2 -0.1(14) . . . . ?
C3 C2 C7 C8 178.8(8) . . . . ?
C1 C2 C7 C8 0.6(12) . . . . ?
C3 C2 C7 C6 -2.3(12) . . . . ?
C1 C2 C7 C6 179.5(8) . . . . ?
C6 C7 C8 C9 -177.0(8) . . . . ?
C2 C7 C8 C9 1.8(12) . . . . ?
C7 C8 C9 C10 -3.0(12) . . . . ?
C7 C8 C9 Pt1 178.6(6) . . . . ?
N1 Pt1 C9 C8 176.9(8) . . . . ?
N2 Pt1 C9 C8 173.6(7) . . . . ?
Cl1 Pt1 C9 C8 -4.4(8) . . . . ?
N1 Pt1 C9 C10 -1.7(6) . . . . ?
N2 Pt1 C9 C10 -4.9(13) . . . . ?
Cl1 Pt1 C9 C10 177.0(5) . . . . ?
C2 C1 C10 C9 0.6(12) . . . . ?
C2 C1 C10 C11 -179.7(8) . . . . ?
C8 C9 C10 C1 1.8(12) . . . . ?
Pt1 C9 C10 C1 -179.5(6) . . . . ?
C8 C9 C10 C11 -177.9(7) . . . . ?
Pt1 C9 C10 C11 0.8(9) . . . . ?
C15 N1 C11 C12 1.2(12) . . . . ?
Pt1 N1 C11 C12 179.5(6) . . . . ?
C15 N1 C11 C10 179.1(7) . . . . ?
Pt1 N1 C11 C10 -2.6(9) . . . . ?
C1 C10 C11 N1 -178.6(8) . . . . ?
C9 C10 C11 N1 1.1(11) . . . . ?
C1 C10 C11 C12 -1.0(14) . . . . ?
C9 C10 C11 C12 178.7(9) . . . . ?
N1 C11 C12 C13 -0.1(13) . . . . ?
C10 C11 C12 C13 -177.6(9) . . . . ?
C11 C12 C13 C14 -2.2(14) . . . . ?
C12 C13 C14 C15 3.4(13) . . . . ?
C11 N1 C15 C14 0.0(12) . . . . ?
Pt1 N1 C15 C14 -178.2(6) . . . . ?
C11 N1 C15 C16 178.5(7) . . . . ?
Pt1 N1 C15 C16 0.3(9) . . . . ?
C13 C14 C15 N1 -2.3(13) . . . . ?
C13 C14 C15 C16 179.4(8) . . . . ?
C20 N2 C16 C17 -0.4(13) . . . . ?
Pt1 N2 C16 C17 -178.6(7) . . . . ?
C20 N2 C16 C15 178.2(8) . . . . ?
Pt1 N2 C16 C15 0.0(9) . . . . ?
N1 C15 C16 N2 -0.2(11) . . . . ?
C14 C15 C16 N2 178.2(8) . . . . ?
N1 C15 C16 C17 178.3(8) . . . . ?
C14 C15 C16 C17 -3.3(14) . . . . ?
N2 C16 C17 C18 0.6(14) . . . . ?
C15 C16 C17 C18 -177.9(9) . . . . ?
C16 C17 C18 C19 1.1(15) . . . . ?
C17 C18 C19 C20 -2.9(15) . . . . ?
C16 N2 C20 C19 -1.5(13) . . . . ?
Pt1 N2 C20 C19 176.4(7) . . . . ?
C18 C19 C20 N2 3.1(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.973
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.194
_exptl_crystal_preparation       Luminescent
