# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_Form_I

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Gefitinib
_chemical_name_common            Iressa
_chemical_melting_point          466-467
_chemical_formula_moiety         'C22 H24 Cl F N4 O3'
_chemical_formula_sum            'C22 H24 Cl F N4 O3'
_chemical_formula_weight         446.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8091(4)
_cell_length_b                   9.6702(4)
_cell_length_c                   12.4941(5)
_cell_angle_alpha                93.700(2)
_cell_angle_beta                 97.546(2)
_cell_angle_gamma                101.939(2)
_cell_volume                     1027.65(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      41.42

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8847
_exptl_absorpt_correction_T_max  0.9264
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19219
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4014
_reflns_number_gt                3758
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0349P)²+0.5056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36289(4) 0.84036(3) 0.92780(3) 0.02890(10) Uani 1 1 d . . .
F1 F 0.38880(9) 1.08785(8) 0.80103(6) 0.02642(17) Uani 1 1 d . . .
N1 N 0.76045(12) 0.54876(11) 0.33582(8) 0.0188(2) Uani 1 1 d . . .
C2 C 0.69740(15) 0.65667(13) 0.35934(10) 0.0197(2) Uani 1 1 d . . .
N3 N 0.65118(12) 0.69656(10) 0.45363(8) 0.0179(2) Uani 1 1 d . . .
C4 C 0.67129(13) 0.61582(12) 0.53397(9) 0.0148(2) Uani 1 1 d . . .
N4 N 0.62740(11) 0.64874(10) 0.63222(8) 0.0162(2) Uani 1 1 d . . .
C5 C 0.76388(13) 0.40384(12) 0.60444(9) 0.0148(2) Uani 1 1 d . . .
C6 C 0.83003(13) 0.29009(12) 0.58549(9) 0.0151(2) Uani 1 1 d . . .
O6 O 0.86115(10) 0.19882(8) 0.65967(6) 0.01706(17) Uani 1 1 d . . .
C7 C 0.87132(13) 0.25908(12) 0.48081(9) 0.0154(2) Uani 1 1 d . . .
O7 O 0.93085(10) 0.14087(9) 0.47258(6) 0.01955(18) Uani 1 1 d . . .
C8 C 0.84878(13) 0.34584(12) 0.40035(9) 0.0162(2) Uani 1 1 d . . .
C9 C 0.78206(13) 0.46508(12) 0.41924(9) 0.0153(2) Uani 1 1 d . . .
C10 C 0.73860(12) 0.49358(11) 0.52158(9) 0.0146(2) Uani 1 1 d . . .
C11 C 0.56557(13) 0.76356(12) 0.66809(9) 0.0151(2) Uani 1 1 d . . .
C12 C 0.50223(13) 0.74997(12) 0.76475(9) 0.0167(2) Uani 1 1 d . . .
C13 C 0.44336(13) 0.85862(13) 0.80875(9) 0.0180(2) Uani 1 1 d . . .
C14 C 0.44576(14) 0.98097(12) 0.75644(10) 0.0187(2) Uani 1 1 d . . .
C15 C 0.50562(14) 0.99540(12) 0.66055(9) 0.0193(2) Uani 1 1 d . . .
C16 C 0.56797(14) 0.88762(12) 0.61607(9) 0.0178(2) Uani 1 1 d . . .
C17 C 0.82814(14) 0.22957(12) 0.76729(9) 0.0162(2) Uani 1 1 d . . .
C18 C 0.88656(14) 0.12239(12) 0.83611(9) 0.0170(2) Uani 1 1 d . . .
C19 C 1.06318(14) 0.16808(12) 0.87308(9) 0.0181(2) Uani 1 1 d . . .
N20 N 1.09799(11) 0.28903(10) 0.95630(7) 0.0158(2) Uani 1 1 d . . .
C21 C 1.25651(14) 0.37529(13) 0.96157(10) 0.0203(2) Uani 1 1 d . . .
C22 C 1.28182(15) 0.50043(13) 1.04670(10) 0.0208(3) Uani 1 1 d . . .
O23 O 1.25847(9) 0.45460(9) 1.15139(6) 0.01839(18) Uani 1 1 d . . .
C24 C 1.10331(14) 0.36932(13) 1.14539(9) 0.0200(2) Uani 1 1 d . . .
C25 C 1.07870(14) 0.24178(13) 1.06344(9) 0.0188(2) Uani 1 1 d . . .
C26 C 0.97682(15) 0.10237(13) 0.37117(10) 0.0201(2) Uani 1 1 d . . .
H2 H 0.6809(17) 0.7162(16) 0.3025(12) 0.024(4) Uiso 1 1 d . . .
H4 H 0.6332(17) 0.5901(16) 0.6794(12) 0.020(4) Uiso 1 1 d . . .
H5 H 0.7355(17) 0.4225(15) 0.6733(12) 0.021(3) Uiso 1 1 d . . .
H8 H 0.8778(17) 0.3283(15) 0.3308(12) 0.021(3) Uiso 1 1 d . . .
H12 H 0.4981(16) 0.6642(16) 0.8002(11) 0.020(3) Uiso 1 1 d . . .
H15 H 0.5051(17) 1.0801(17) 0.6267(12) 0.025(4) Uiso 1 1 d . . .
H16 H 0.6104(17) 0.8997(15) 0.5517(12) 0.020(3) Uiso 1 1 d . . .
H17A H 0.7159(17) 0.2227(14) 0.7650(11) 0.016(3) Uiso 1 1 d . . .
H17B H 0.8849(16) 0.3250(15) 0.7953(11) 0.016(3) Uiso 1 1 d . . .
H18A H 0.8594(16) 0.0287(15) 0.7941(11) 0.019(3) Uiso 1 1 d . . .
H18B H 0.8316(16) 0.1134(14) 0.8985(11) 0.017(3) Uiso 1 1 d . . .
H19A H 1.1087(16) 0.0861(15) 0.8986(11) 0.019(3) Uiso 1 1 d . . .
H19B H 1.1136(16) 0.1992(15) 0.8106(12) 0.019(3) Uiso 1 1 d . . .
H21A H 1.2680(17) 0.4103(15) 0.8919(12) 0.021(3) Uiso 1 1 d . . .
H21B H 1.3369(18) 0.3185(16) 0.9796(12) 0.023(4) Uiso 1 1 d . . .
H22A H 1.3885(18) 0.5569(15) 1.0548(11) 0.022(3) Uiso 1 1 d . . .
H22B H 1.2072(17) 0.5621(15) 1.0269(11) 0.021(3) Uiso 1 1 d . . .
H24A H 1.0271(17) 0.4281(15) 1.1269(11) 0.021(3) Uiso 1 1 d . . .
H24B H 1.0938(17) 0.3406(15) 1.2184(12) 0.021(3) Uiso 1 1 d . . .
H25A H 1.1542(17) 0.1819(15) 1.0852(11) 0.020(3) Uiso 1 1 d . . .
H25B H 0.9721(18) 0.1842(16) 1.0629(12) 0.023(4) Uiso 1 1 d . . .
H26A H 0.8879(18) 0.0890(15) 0.3112(12) 0.024(4) Uiso 1 1 d . . .
H26B H 1.0102(17) 0.0146(16) 0.3809(11) 0.021(3) Uiso 1 1 d . . .
H26C H 1.0642(18) 0.1777(16) 0.3542(12) 0.024(4) 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 C13 1.7335(12) . ?
F1 C14 1.3579(13) . ?
N1 C2 1.3141(16) . ?
N1 C9 1.3776(14) . ?
C2 N3 1.3545(15) . ?
C2 H2 0.958(15) . ?
N3 C4 1.3268(15) . ?
C4 N4 1.3722(15) . ?
C4 C10 1.4364(15) . ?
N4 C11 1.4072(15) . ?
N4 H4 0.848(16) . ?
C5 C6 1.3687(16) . ?
C5 C10 1.4177(16) . ?
C5 H5 0.944(15) . ?
C6 O6 1.3608(13) . ?
C6 C7 1.4326(15) . ?
O6 C17 1.4380(13) . ?
C7 O7 1.3562(14) . ?
C7 C8 1.3709(16) . ?
O7 C26 1.4297(14) . ?
C8 C9 1.4187(16) . ?
C8 H8 0.952(15) . ?
C9 C10 1.4086(15) . ?
C11 C12 1.3979(16) . ?
C11 C16 1.3986(16) . ?
C12 C13 1.3787(16) . ?
C12 H12 0.962(15) . ?
C13 C14 1.3858(17) . ?
C14 C15 1.3748(17) . ?
C15 C16 1.3924(17) . ?
C15 H15 0.946(16) . ?
C16 H16 0.934(15) . ?
C17 C18 1.5159(15) . ?
C17 H17A 0.974(14) . ?
C17 H17B 0.972(14) . ?
C18 C19 1.5263(16) . ?
C18 H18A 0.985(14) . ?
C18 H18B 0.970(14) . ?
C19 N20 1.4676(14) . ?
C19 H19A 1.011(14) . ?
C19 H19B 0.981(15) . ?
N20 C25 1.4615(14) . ?
N20 C21 1.4619(15) . ?
C21 C22 1.5183(17) . ?
C21 H21A 0.964(15) . ?
C21 H21B 0.994(15) . ?
C22 O23 1.4344(14) . ?
C22 H22A 0.973(15) . ?
C22 H22B 0.993(15) . ?
O23 C24 1.4327(14) . ?
C24 C25 1.5115(17) . ?
C24 H24A 0.981(15) . ?
C24 H24B 0.980(15) . ?
C25 H25A 0.992(15) . ?
C25 H25B 0.986(15) . ?
C26 H26A 0.991(15) . ?
C26 H26B 0.964(15) . ?
C26 H26C 0.999(15) . ?

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
C2 N1 C9 114.96(10) . . ?
N1 C2 N3 129.08(11) . . ?
N1 C2 H2 116.5(9) . . ?
N3 C2 H2 114.4(9) . . ?
C4 N3 C2 116.08(10) . . ?
N3 C4 N4 119.79(10) . . ?
N3 C4 C10 121.86(10) . . ?
N4 C4 C10 118.35(10) . . ?
C4 N4 C11 130.43(10) . . ?
C4 N4 H4 117.0(10) . . ?
C11 N4 H4 112.5(10) . . ?
C6 C5 C10 120.42(10) . . ?
C6 C5 H5 119.5(9) . . ?
C10 C5 H5 120.1(9) . . ?
O6 C6 C5 125.06(10) . . ?
O6 C6 C7 114.81(10) . . ?
C5 C6 C7 120.13(10) . . ?
C6 O6 C17 116.72(9) . . ?
O7 C7 C8 126.27(10) . . ?
O7 C7 C6 113.77(10) . . ?
C8 C7 C6 119.96(10) . . ?
C7 O7 C26 117.70(9) . . ?
C7 C8 C9 120.49(10) . . ?
C7 C8 H8 121.2(9) . . ?
C9 C8 H8 118.3(9) . . ?
N1 C9 C10 122.08(10) . . ?
N1 C9 C8 118.53(10) . . ?
C10 C9 C8 119.39(10) . . ?
C9 C10 C5 119.58(10) . . ?
C9 C10 C4 115.95(10) . . ?
C5 C10 C4 124.47(10) . . ?
C12 C11 C16 119.59(10) . . ?
C12 C11 N4 115.57(10) . . ?
C16 C11 N4 124.82(10) . . ?
C13 C12 C11 120.14(11) . . ?
C13 C12 H12 119.8(9) . . ?
C11 C12 H12 120.1(8) . . ?
C12 C13 C14 119.87(11) . . ?
C12 C13 Cl1 119.94(9) . . ?
C14 C13 Cl1 120.18(9) . . ?
F1 C14 C15 119.83(10) . . ?
F1 C14 C13 119.37(10) . . ?
C15 C14 C13 120.80(11) . . ?
C14 C15 C16 120.00(11) . . ?
C14 C15 H15 118.7(9) . . ?
C16 C15 H15 121.3(9) . . ?
C15 C16 C11 119.59(11) . . ?
C15 C16 H16 119.1(9) . . ?
C11 C16 H16 121.3(9) . . ?
O6 C17 C18 106.52(9) . . ?
O6 C17 H17A 109.4(8) . . ?
C18 C17 H17A 112.1(8) . . ?
O6 C17 H17B 109.3(8) . . ?
C18 C17 H17B 109.7(8) . . ?
H17A C17 H17B 109.7(11) . . ?
C17 C18 C19 110.91(9) . . ?
C17 C18 H18A 109.1(8) . . ?
C19 C18 H18A 111.0(8) . . ?
C17 C18 H18B 108.9(8) . . ?
C19 C18 H18B 110.1(8) . . ?
H18A C18 H18B 106.8(11) . . ?
N20 C19 C18 110.22(9) . . ?
N20 C19 H19A 112.1(8) . . ?
C18 C19 H19A 111.4(8) . . ?
N20 C19 H19B 107.8(8) . . ?
C18 C19 H19B 108.4(8) . . ?
H19A C19 H19B 106.7(11) . . ?
C25 N20 C21 108.64(9) . . ?
C25 N20 C19 111.16(9) . . ?
C21 N20 C19 112.68(9) . . ?
N20 C21 C22 109.57(10) . . ?
N20 C21 H21A 108.9(9) . . ?
C22 C21 H21A 109.1(9) . . ?
N20 C21 H21B 111.2(9) . . ?
C22 C21 H21B 109.5(9) . . ?
H21A C21 H21B 108.6(12) . . ?
O23 C22 C21 111.54(10) . . ?
O23 C22 H22A 106.4(8) . . ?
C21 C22 H22A 111.4(9) . . ?
O23 C22 H22B 107.9(8) . . ?
C21 C22 H22B 110.4(8) . . ?
H22A C22 H22B 109.0(12) . . ?
C24 O23 C22 109.57(9) . . ?
O23 C24 C25 110.49(10) . . ?
O23 C24 H24A 108.9(9) . . ?
C25 C24 H24A 111.5(8) . . ?
O23 C24 H24B 106.2(8) . . ?
C25 C24 H24B 111.3(8) . . ?
H24A C24 H24B 108.2(12) . . ?
N20 C25 C24 109.64(9) . . ?
N20 C25 H25A 110.4(8) . . ?
C24 C25 H25A 110.1(8) . . ?
N20 C25 H25B 110.7(8) . . ?
C24 C25 H25B 108.4(8) . . ?
H25A C25 H25B 107.6(12) . . ?
O7 C26 H26A 111.1(9) . . ?
O7 C26 H26B 104.8(9) . . ?
H26A C26 H26B 110.8(12) . . ?
O7 C26 H26C 110.5(8) . . ?
H26A C26 H26C 108.3(12) . . ?
H26B C26 H26C 111.2(12) . . ?

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 N1 C2 N3 0.02(19) . . . . ?
N1 C2 N3 C4 -0.28(19) . . . . ?
C2 N3 C4 N4 -179.93(10) . . . . ?
C2 N3 C4 C10 0.19(16) . . . . ?
N3 C4 N4 C11 -2.82(18) . . . . ?
C10 C4 N4 C11 177.07(10) . . . . ?
C10 C5 C6 O6 179.08(10) . . . . ?
C10 C5 C6 C7 -1.30(16) . . . . ?
C5 C6 O6 C17 -3.07(16) . . . . ?
C7 C6 O6 C17 177.28(9) . . . . ?
O6 C6 C7 O7 1.73(14) . . . . ?
C5 C6 C7 O7 -177.93(10) . . . . ?
O6 C6 C7 C8 -178.44(10) . . . . ?
C5 C6 C7 C8 1.90(16) . . . . ?
C8 C7 O7 C26 0.77(16) . . . . ?
C6 C7 O7 C26 -179.41(10) . . . . ?
O7 C7 C8 C9 178.66(10) . . . . ?
C6 C7 C8 C9 -1.15(16) . . . . ?
C2 N1 C9 C10 0.33(16) . . . . ?
C2 N1 C9 C8 179.67(10) . . . . ?
C7 C8 C9 N1 -179.52(10) . . . . ?
C7 C8 C9 C10 -0.16(16) . . . . ?
N1 C9 C10 C5 -179.91(10) . . . . ?
C8 C9 C10 C5 0.75(16) . . . . ?
N1 C9 C10 C4 -0.40(16) . . . . ?
C8 C9 C10 C4 -179.73(10) . . . . ?
C6 C5 C10 C9 -0.01(16) . . . . ?
C6 C5 C10 C4 -179.48(10) . . . . ?
N3 C4 C10 C9 0.12(15) . . . . ?
N4 C4 C10 C9 -179.76(10) . . . . ?
N3 C4 C10 C5 179.61(10) . . . . ?
N4 C4 C10 C5 -0.27(16) . . . . ?
C4 N4 C11 C12 166.84(11) . . . . ?
C4 N4 C11 C16 -15.05(19) . . . . ?
C16 C11 C12 C13 -0.38(17) . . . . ?
N4 C11 C12 C13 177.84(10) . . . . ?
C11 C12 C13 C14 0.59(17) . . . . ?
C11 C12 C13 Cl1 179.26(9) . . . . ?
C12 C13 C14 F1 -179.40(10) . . . . ?
Cl1 C13 C14 F1 1.94(16) . . . . ?
C12 C13 C14 C15 0.31(18) . . . . ?
Cl1 C13 C14 C15 -178.35(9) . . . . ?
F1 C14 C15 C16 178.28(10) . . . . ?
C13 C14 C15 C16 -1.42(18) . . . . ?
C14 C15 C16 C11 1.62(17) . . . . ?
C12 C11 C16 C15 -0.72(17) . . . . ?
N4 C11 C16 C15 -178.77(11) . . . . ?
C6 O6 C17 C18 -174.73(9) . . . . ?
O6 C17 C18 C19 81.34(11) . . . . ?
C17 C18 C19 N20 72.27(12) . . . . ?
C18 C19 N20 C25 82.60(11) . . . . ?
C18 C19 N20 C21 -155.17(9) . . . . ?
C25 N20 C21 C22 -58.15(12) . . . . ?
C19 N20 C21 C22 178.21(9) . . . . ?
N20 C21 C22 O23 58.08(13) . . . . ?
C21 C22 O23 C24 -57.86(13) . . . . ?
C22 O23 C24 C25 58.84(12) . . . . ?
C21 N20 C25 C24 59.77(12) . . . . ?
C19 N20 C25 C24 -175.69(9) . . . . ?
O23 C24 C25 N20 -60.69(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C25 H25B Cl1 0.986(15) 2.930(15) 3.8236(13) 151.1(11) 2_667
C26 H26B O7 0.964(15) 2.512(15) 3.3124(15) 140.4(11) 2_756
C26 H26B O6 0.964(15) 2.604(15) 3.5197(15) 158.7(11) 2_756
C2 H2 F1 0.958(15) 2.496(16) 3.4220(14) 162.7(12) 2_676
C12 H12 O23 0.962(15) 2.655(14) 3.2966(14) 124.5(10) 2_767
C5 H5 O23 0.944(15) 2.412(15) 3.3091(14) 158.6(12) 2_767
N4 H4 O23 0.848(16) 2.308(15) 3.0609(12) 148.2(13) 2_767

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
_database_code_depnum_ccdc_archive 'CCDC 990393'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Form_II

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Gefitinib
_chemical_name_common            Iressa
_chemical_melting_point          466-467
_chemical_formula_moiety         'C22 H24 Cl F N4 O3'
_chemical_formula_sum            'C22 H24 Cl F N4 O3'
_chemical_formula_weight         446.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1645(2)
_cell_length_b                   10.8025(3)
_cell_length_c                   14.3429(4)
_cell_angle_alpha                80.3020(10)
_cell_angle_beta                 75.6620(10)
_cell_angle_gamma                89.2670(10)
_cell_volume                     1059.63(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      68.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    1.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8288
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker PHOTON-100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22103
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         68.30
_reflns_number_total             3826
_reflns_number_gt                3432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0382P)²+0.6108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3826
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.24746(6) 0.46707(4) 0.92400(3) 0.02810(13) Uani 1 1 d . . .
F1 F -0.13372(14) 0.29445(8) 0.78237(7) 0.0218(2) Uani 1 1 d . . .
N1 N 0.26223(18) 0.99641(12) 0.36139(9) 0.0162(3) Uani 1 1 d . . .
C2 C 0.2057(2) 0.87776(15) 0.38452(11) 0.0167(3) Uani 1 1 d . . .
N3 N 0.15860(18) 0.80429(12) 0.47327(9) 0.0159(3) Uani 1 1 d . . .
C4 C 0.1720(2) 0.85805(14) 0.54808(11) 0.0140(3) Uani 1 1 d . . .
N4 N 0.11971(19) 0.78805(13) 0.64019(10) 0.0159(3) Uani 1 1 d . . .
C5 C 0.2645(2) 1.04782(14) 0.61083(11) 0.0140(3) Uani 1 1 d . . .
C6 C 0.3265(2) 1.17103(14) 0.59037(11) 0.0137(3) Uani 1 1 d . . .
O6 O 0.35968(15) 1.23991(10) 0.65629(7) 0.0157(2) Uani 1 1 d . . .
C7 C 0.3628(2) 1.23925(14) 0.49248(11) 0.0137(3) Uani 1 1 d . . .
O7 O 0.41893(15) 1.36118(10) 0.48211(7) 0.0168(2) Uani 1 1 d . . .
C8 C 0.3400(2) 1.17957(14) 0.41878(11) 0.0145(3) Uani 1 1 d . . .
C9 C 0.2790(2) 1.05237(14) 0.43855(11) 0.0137(3) Uani 1 1 d . . .
C10 C 0.2377(2) 0.98585(14) 0.53513(11) 0.0134(3) Uani 1 1 d . . .
C11 C 0.0516(2) 0.66265(14) 0.66882(11) 0.0146(3) Uani 1 1 d . . .
C12 C -0.0543(2) 0.62901(15) 0.76559(12) 0.0178(3) Uani 1 1 d . . .
C13 C -0.1165(2) 0.50630(15) 0.80324(11) 0.0182(3) Uani 1 1 d . . .
C14 C -0.0753(2) 0.41574(14) 0.74407(11) 0.0167(3) Uani 1 1 d . . .
C15 C 0.0254(2) 0.44710(15) 0.64801(12) 0.0172(3) Uani 1 1 d . . .
C16 C 0.0901(2) 0.57019(15) 0.60946(11) 0.0164(3) Uani 1 1 d . . .
C17 C 0.3331(2) 1.17847(15) 0.75596(11) 0.0161(3) Uani 1 1 d . . .
C18 C 0.3742(2) 1.27930(15) 0.81054(11) 0.0189(3) Uani 1 1 d . . .
C19 C 0.4027(2) 1.22877(16) 0.91164(12) 0.0205(3) Uani 1 1 d . . .
N20 N 0.24178(19) 1.15155(13) 0.97851(9) 0.0186(3) Uani 1 1 d . . .
C21 C 0.0651(2) 1.22327(16) 0.99704(12) 0.0208(4) Uani 1 1 d . . .
C22 C -0.0947(3) 1.14835(17) 1.07485(12) 0.0233(4) Uani 1 1 d . . .
O23 O -0.03761(17) 1.10931(11) 1.16443(8) 0.0225(3) Uani 1 1 d . . .
C24 C 0.1317(3) 1.03618(16) 1.14609(12) 0.0236(4) Uani 1 1 d . . .
C25 C 0.2943(3) 1.11055(16) 1.07125(12) 0.0217(4) Uani 1 1 d . . .
C26 C 0.4458(2) 1.43628(15) 0.38690(11) 0.0177(3) Uani 1 1 d . . .
H2 H 0.193(2) 0.8363(17) 0.3326(13) 0.017(4) Uiso 1 1 d . . .
H4 H 0.106(3) 0.8258(18) 0.6851(14) 0.015(5) Uiso 1 1 d . . .
H5 H 0.242(2) 1.0040(16) 0.6761(13) 0.015(4) Uiso 1 1 d . . .
H8 H 0.366(3) 1.2222(17) 0.3520(14) 0.019(4) Uiso 1 1 d . . .
H12 H -0.084(3) 0.6894(19) 0.8056(14) 0.027(5) Uiso 1 1 d . . .
H15 H 0.053(3) 0.3859(18) 0.6095(13) 0.019(4) Uiso 1 1 d . . .
H16 H 0.163(3) 0.5923(17) 0.5441(14) 0.021(5) Uiso 1 1 d . . .
H17A H 0.423(3) 1.1088(17) 0.7600(13) 0.017(4) Uiso 1 1 d . . .
H17B H 0.203(3) 1.1452(16) 0.7803(12) 0.013(4) Uiso 1 1 d . . .
H18A H 0.272(3) 1.3442(18) 0.8149(13) 0.020(4) Uiso 1 1 d . . .
H18B H 0.495(3) 1.3232(17) 0.7738(13) 0.021(5) Uiso 1 1 d . . .
H19A H 0.431(3) 1.3042(18) 0.9413(13) 0.020(5) Uiso 1 1 d . . .
H19B H 0.518(3) 1.1756(17) 0.9047(13) 0.020(5) Uiso 1 1 d . . .
H21A H 0.023(3) 1.2432(17) 0.9366(14) 0.019(4) Uiso 1 1 d . . .
H21B H 0.088(3) 1.306(2) 1.0159(14) 0.029(5) Uiso 1 1 d . . .
H22A H -0.134(3) 1.0739(19) 1.0526(14) 0.023(5) Uiso 1 1 d . . .
H22B H -0.209(3) 1.2015(17) 1.0919(13) 0.020(4) Uiso 1 1 d . . .
H24A H 0.164(3) 1.0154(18) 1.2089(15) 0.028(5) Uiso 1 1 d . . .
H24B H 0.100(3) 0.9602(19) 1.1251(14) 0.022(5) Uiso 1 1 d . . .
H25A H 0.330(3) 1.1862(18) 1.0987(13) 0.022(5) Uiso 1 1 d . . .
H25B H 0.413(3) 1.0553(19) 1.0596(14) 0.029(5) Uiso 1 1 d . . .
H26A H 0.324(3) 1.4370(17) 0.3651(13) 0.017(4) Uiso 1 1 d . . .
H26B H 0.548(3) 1.4035(17) 0.3399(13) 0.016(4) Uiso 1 1 d . . .
H26C H 0.482(3) 1.5205(19) 0.3934(14) 0.023(5) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.7373(16) . ?
F1 C14 1.3606(18) . ?
N1 C2 1.312(2) . ?
N1 C9 1.3776(19) . ?
C2 N3 1.348(2) . ?
C2 H2 0.954(18) . ?
N3 C4 1.327(2) . ?
C4 N4 1.372(2) . ?
C4 C10 1.431(2) . ?
N4 C11 1.404(2) . ?
N4 H4 0.804(19) . ?
C5 C6 1.369(2) . ?
C5 C10 1.420(2) . ?
C5 H5 0.951(18) . ?
C6 O6 1.3627(18) . ?
C6 C7 1.434(2) . ?
O6 C17 1.4385(18) . ?
C7 O7 1.3553(19) . ?
C7 C8 1.370(2) . ?
O7 C26 1.4354(18) . ?
C8 C9 1.408(2) . ?
C8 H8 0.964(18) . ?
C9 C10 1.411(2) . ?
C11 C12 1.396(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.93(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.375(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.920(19) . ?
C16 H16 0.945(19) . ?
C17 C18 1.515(2) . ?
C17 H17A 0.990(19) . ?
C17 H17B 0.963(18) . ?
C18 C19 1.523(2) . ?
C18 H18A 1.005(19) . ?
C18 H18B 0.98(2) . ?
C19 N20 1.467(2) . ?
C19 H19A 1.025(19) . ?
C19 H19B 0.996(19) . ?
N20 C21 1.466(2) . ?
N20 C25 1.467(2) . ?
C21 C22 1.516(2) . ?
C21 H21A 0.976(19) . ?
C21 H21B 1.00(2) . ?
C22 O23 1.438(2) . ?
C22 H22A 0.98(2) . ?
C22 H22B 0.997(19) . ?
O23 C24 1.432(2) . ?
C24 C25 1.506(2) . ?
C24 H24A 0.97(2) . ?
C24 H24B 0.97(2) . ?
C25 H25A 1.03(2) . ?
C25 H25B 1.03(2) . ?
C26 H26A 1.000(19) . ?
C26 H26B 0.971(19) . ?
C26 H26C 0.98(2) . ?

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
C2 N1 C9 115.13(13) . . ?
N1 C2 N3 128.93(14) . . ?
N1 C2 H2 117.1(11) . . ?
N3 C2 H2 114.0(11) . . ?
C4 N3 C2 116.23(13) . . ?
N3 C4 N4 118.30(14) . . ?
N3 C4 C10 121.95(14) . . ?
N4 C4 C10 119.75(13) . . ?
C4 N4 C11 128.88(13) . . ?
C4 N4 H4 116.7(13) . . ?
C11 N4 H4 113.3(13) . . ?
C6 C5 C10 120.30(14) . . ?
C6 C5 H5 119.1(11) . . ?
C10 C5 H5 120.6(11) . . ?
O6 C6 C5 125.71(13) . . ?
O6 C6 C7 113.94(13) . . ?
C5 C6 C7 120.35(13) . . ?
C6 O6 C17 118.05(11) . . ?
O7 C7 C8 125.61(13) . . ?
O7 C7 C6 114.72(13) . . ?
C8 C7 C6 119.67(14) . . ?
C7 O7 C26 117.24(12) . . ?
C7 C8 C9 120.56(14) . . ?
C7 C8 H8 121.7(11) . . ?
C9 C8 H8 117.7(11) . . ?
N1 C9 C8 118.10(13) . . ?
N1 C9 C10 121.91(14) . . ?
C8 C9 C10 120.00(14) . . ?
C9 C10 C5 119.07(14) . . ?
C9 C10 C4 115.79(13) . . ?
C5 C10 C4 125.14(14) . . ?
C12 C11 C16 118.93(14) . . ?
C12 C11 N4 116.06(14) . . ?
C16 C11 N4 124.94(14) . . ?
C13 C12 C11 120.82(15) . . ?
C13 C12 H12 119.0(12) . . ?
C11 C12 H12 120.2(12) . . ?
C12 C13 C14 119.57(14) . . ?
C12 C13 Cl1 119.82(12) . . ?
C14 C13 Cl1 120.60(12) . . ?
F1 C14 C15 120.17(14) . . ?
F1 C14 C13 119.18(14) . . ?
C15 C14 C13 120.65(15) . . ?
C14 C15 C16 120.31(15) . . ?
C14 C15 H15 119.9(11) . . ?
C16 C15 H15 119.8(11) . . ?
C15 C16 C11 119.70(14) . . ?
C15 C16 H16 121.1(11) . . ?
C11 C16 H16 119.2(11) . . ?
O6 C17 C18 105.35(12) . . ?
O6 C17 H17A 110.3(10) . . ?
C18 C17 H17A 110.9(10) . . ?
O6 C17 H17B 109.0(10) . . ?
C18 C17 H17B 112.0(10) . . ?
H17A C17 H17B 109.2(15) . . ?
C17 C18 C19 114.06(14) . . ?
C17 C18 H18A 111.4(11) . . ?
C19 C18 H18A 110.2(10) . . ?
C17 C18 H18B 108.5(11) . . ?
C19 C18 H18B 105.7(11) . . ?
H18A C18 H18B 106.6(15) . . ?
N20 C19 C18 115.43(13) . . ?
N20 C19 H19A 110.3(10) . . ?
C18 C19 H19A 107.5(10) . . ?
N20 C19 H19B 106.9(11) . . ?
C18 C19 H19B 108.9(10) . . ?
H19A C19 H19B 107.6(15) . . ?
C21 N20 C25 108.80(12) . . ?
C21 N20 C19 111.29(13) . . ?
C25 N20 C19 108.01(13) . . ?
N20 C21 C22 111.22(14) . . ?
N20 C21 H21A 108.7(11) . . ?
C22 C21 H21A 108.7(11) . . ?
N20 C21 H21B 111.7(11) . . ?
C22 C21 H21B 110.2(11) . . ?
H21A C21 H21B 106.2(15) . . ?
O23 C22 C21 111.62(14) . . ?
O23 C22 H22A 109.1(11) . . ?
C21 C22 H22A 111.1(11) . . ?
O23 C22 H22B 105.5(10) . . ?
C21 C22 H22B 110.2(11) . . ?
H22A C22 H22B 109.2(15) . . ?
C24 O23 C22 109.49(12) . . ?
O23 C24 C25 110.91(14) . . ?
O23 C24 H24A 104.9(12) . . ?
C25 C24 H24A 110.8(12) . . ?
O23 C24 H24B 108.6(11) . . ?
C25 C24 H24B 111.5(11) . . ?
H24A C24 H24B 109.9(16) . . ?
N20 C25 C24 111.35(14) . . ?
N20 C25 H25A 110.9(10) . . ?
C24 C25 H25A 108.8(10) . . ?
N20 C25 H25B 109.3(11) . . ?
C24 C25 H25B 108.9(11) . . ?
H25A C25 H25B 107.5(15) . . ?
O7 C26 H26A 110.1(10) . . ?
O7 C26 H26B 110.6(10) . . ?
H26A C26 H26B 109.2(14) . . ?
O7 C26 H26C 106.0(11) . . ?
H26A C26 H26C 111.0(15) . . ?
H26B C26 H26C 109.9(15) . . ?

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 N1 C2 N3 1.4(2) . . . . ?
N1 C2 N3 C4 -0.6(2) . . . . ?
C2 N3 C4 N4 177.99(13) . . . . ?
C2 N3 C4 C10 -1.6(2) . . . . ?
N3 C4 N4 C11 0.2(2) . . . . ?
C10 C4 N4 C11 179.81(14) . . . . ?
C10 C5 C6 O6 -179.15(13) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C5 C6 O6 C17 1.8(2) . . . . ?
C7 C6 O6 C17 -178.10(12) . . . . ?
O6 C6 C7 O7 -1.63(18) . . . . ?
C5 C6 C7 O7 178.46(13) . . . . ?
O6 C6 C7 C8 178.19(13) . . . . ?
C5 C6 C7 C8 -1.7(2) . . . . ?
C8 C7 O7 C26 3.9(2) . . . . ?
C6 C7 O7 C26 -176.26(13) . . . . ?
O7 C7 C8 C9 -179.38(13) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C2 N1 C9 C8 179.68(13) . . . . ?
C2 N1 C9 C10 -0.1(2) . . . . ?
C7 C8 C9 N1 -178.73(13) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
N1 C9 C10 C5 177.76(13) . . . . ?
C8 C9 C10 C5 -2.0(2) . . . . ?
N1 C9 C10 C4 -1.8(2) . . . . ?
C8 C9 C10 C4 178.46(13) . . . . ?
C6 C5 C10 C9 1.1(2) . . . . ?
C6 C5 C10 C4 -179.40(14) . . . . ?
N3 C4 C10 C9 2.7(2) . . . . ?
N4 C4 C10 C9 -176.91(13) . . . . ?
N3 C4 C10 C5 -176.84(14) . . . . ?
N4 C4 C10 C5 3.6(2) . . . . ?
C4 N4 C11 C12 -157.57(15) . . . . ?
C4 N4 C11 C16 25.6(2) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
N4 C11 C12 C13 -175.46(14) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C11 C12 C13 Cl1 179.81(12) . . . . ?
C12 C13 C14 F1 178.65(14) . . . . ?
Cl1 C13 C14 F1 -2.0(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
Cl1 C13 C14 C15 178.83(12) . . . . ?
F1 C14 C15 C16 -178.10(13) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C12 C11 C16 C15 -1.1(2) . . . . ?
N4 C11 C16 C15 175.72(14) . . . . ?
C6 O6 C17 C18 -178.26(12) . . . . ?
O6 C17 C18 C19 -165.77(13) . . . . ?
C17 C18 C19 N20 -57.2(2) . . . . ?
C18 C19 N20 C21 -61.06(18) . . . . ?
C18 C19 N20 C25 179.58(14) . . . . ?
C25 N20 C21 C22 -54.61(17) . . . . ?
C19 N20 C21 C22 -173.49(13) . . . . ?
N20 C21 C22 O23 56.83(18) . . . . ?
C21 C22 O23 C24 -57.82(18) . . . . ?
C22 O23 C24 C25 58.75(17) . . . . ?
C21 N20 C25 C24 56.01(17) . . . . ?
C19 N20 C25 C24 176.94(14) . . . . ?
O23 C24 C25 N20 -59.20(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O23 0.804(19) 2.32(2) 3.1052(17) 166.9(17) 2_577
C5 H5 O23 0.951(18) 2.514(18) 3.3980(18) 154.6(14) 2_577
C12 H12 O23 0.93(2) 2.49(2) 3.281(2) 142.6(16) 2_577
C2 H2 F1 0.954(18) 2.458(19) 3.4048(18) 171.6(15) 2_566
C26 H26C O6 0.98(2) 2.75(2) 3.678(2) 160.1(15) 2_686
C26 H26C O7 0.98(2) 2.60(2) 3.405(2) 140.4(14) 2_686
C19 H19A Cl1 1.025(19) 2.852(19) 3.6714(17) 137.3(13) 1_665

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        68.30
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_database_code_depnum_ccdc_archive 'CCDC 990394'
