# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_c:\xrd\fluf44~1\new
_database_code_depnum_ccdc_archive 'CCDC 1018667'
_audit_update_record             
;
2014-08-10 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid and4,4'bipyridine complex"
_chemical_name_common            
;
flufenamic acid and 4,4'-Bipyridine complex
;
_chemical_melting_point          400K
_chemical_formula_moiety         '3(C14 H10 F3 N O2), 1.5(C10 H8 N2)'
_chemical_formula_sum            'C57 H42 F9 N6 O6'
_chemical_formula_weight         1077.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.8293(4)
_cell_length_b                   10.3830(6)
_cell_length_c                   24.9908(13)
_cell_angle_alpha                84.684(4)
_cell_angle_beta                 81.333(4)
_cell_angle_gamma                71.773(4)
_cell_volume                     2392.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3347
_cell_measurement_theta_min      2.7897
_cell_measurement_theta_max      28.7737

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1110
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89221
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_reflns_number            19891
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.35
_reflns_number_total             8741
_reflns_number_gt                4684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0937P)²+0.3064P] 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         8741
_refine_ls_number_parameters     871
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0427(3) 0.6412(3) 0.44141(11) 0.0249(7) Uani 1 1 d . . .
C1 C 0.8270(5) 0.7961(5) 0.03411(15) 0.0457(11) Uani 1 1 d . . .
H14 H 0.617(3) 0.965(3) 0.5125(11) 0.011(7) Uiso 1 1 d . . .
H12 H 0.537(3) 0.681(3) 0.4468(13) 0.015(8) Uiso 1 1 d . . .
H2 H -0.045(3) 0.629(3) 0.5164(12) 0.021(8) Uiso 1 1 d . . .
H16A H 0.527(3) 0.357(3) 0.1903(13) 0.021(9) Uiso 1 1 d . . .
H16C H 0.806(3) 0.711(3) 0.1356(12) 0.019(8) Uiso 1 1 d . . .
H5B H -0.032(4) 0.232(4) 0.3542(15) 0.036(10) Uiso 1 1 d . . .
H13A H 0.482(3) 0.109(3) 0.0491(12) 0.015(8) Uiso 1 1 d . . .
H8 H 0.310(4) 0.667(3) 0.5956(13) 0.028(9) Uiso 1 1 d . . .
H7C H 0.433(3) 0.657(3) 0.2280(12) 0.019(8) Uiso 1 1 d . . .
H11 H 0.728(4) 0.697(3) 0.4898(13) 0.026(9) Uiso 1 1 d . . .
H13B H 0.171(3) 0.459(3) 0.0417(13) 0.028(9) Uiso 1 1 d . . .
H12A H 0.444(3) 0.037(3) 0.1392(12) 0.020(9) Uiso 1 1 d . . .
H14A H 0.547(3) 0.306(3) 0.0360(12) 0.010(8) Uiso 1 1 d . . .
H8B H -0.087(3) 0.448(3) 0.1872(14) 0.027(9) Uiso 1 1 d . . .
H9 H 0.506(3) 0.685(3) 0.6322(13) 0.018(8) Uiso 1 1 d . . .
H5 H 0.363(4) 0.672(3) 0.4100(13) 0.027(9) Uiso 1 1 d . . .
H16B H 0.195(4) 0.700(4) 0.1932(15) 0.035(10) Uiso 1 1 d . . .
H17 H 1.033(4) 1.002(3) 0.4066(14) 0.032(9) Uiso 1 1 d . . .
H5A H 0.311(3) -0.117(4) 0.3628(14) 0.030(9) Uiso 1 1 d . . .
H6B H -0.212(3) 0.214(3) 0.3072(12) 0.019(8) Uiso 1 1 d . . .
H6C H 0.466(4) 0.538(4) 0.3154(13) 0.031(10) Uiso 1 1 d . . .
H6A H 0.131(4) -0.134(4) 0.3176(13) 0.033(10) Uiso 1 1 d . . .
H5C H 0.644(4) 0.556(4) 0.3611(15) 0.038(10) Uiso 1 1 d . . .
H8A H 0.227(4) 0.117(4) 0.1951(15) 0.040(10) Uiso 1 1 d . . .
H10A H 0.511(4) 0.157(4) 0.2514(15) 0.037(11) Uiso 1 1 d . . .
H3 H 0.135(4) 0.650(4) 0.5586(17) 0.051(12) Uiso 1 1 d . . .
H8C H 0.580(4) 0.785(4) 0.1970(14) 0.029(10) Uiso 1 1 d . . .
H6 H 0.167(3) 0.646(3) 0.3754(13) 0.020(8) Uiso 1 1 d . . .
H7A H 0.092(4) -0.017(3) 0.2324(13) 0.029(9) Uiso 1 1 d . . .
H15 H 0.799(3) 0.986(3) 0.5549(14) 0.027(9) Uiso 1 1 d . . .
H10C H 0.852(4) 0.828(4) 0.2533(16) 0.041(12) Uiso 1 1 d . . .
H12B H 0.135(3) 0.379(4) 0.1349(12) 0.025(9) Uiso 1 1 d . . .
H18 H 0.830(4) 0.994(4) 0.3719(15) 0.036(10) Uiso 1 1 d . . .
H10B H 0.185(4) 0.497(4) 0.2489(17) 0.052(13) Uiso 1 1 d . . .
H7B H -0.240(4) 0.332(4) 0.2215(14) 0.042(10) Uiso 1 1 d . . .
H14B H 0.227(4) 0.665(4) 0.0321(15) 0.037(11) Uiso 1 1 d . . .
H1C H 0.903(5) 0.620(4) 0.4045(16) 0.051(13) Uiso 1 1 d . . .
H13C H 0.893(4) 1.153(4) 0.1152(15) 0.054(12) Uiso 1 1 d . . .
H1A H 0.571(5) -0.039(4) 0.4026(17) 0.061(13) Uiso 1 1 d . . .
H12C H 0.839(4) 1.042(4) 0.2046(14) 0.031(10) Uiso 1 1 d . . .
H1B H 0.232(5) 0.294(5) 0.4010(19) 0.077(16) Uiso 1 1 d . . .
H14C H 0.875(4) 1.036(4) 0.0385(14) 0.035(9) Uiso 1 1 d . . .
C2 C 0.0368(4) 0.6428(4) 0.49496(14) 0.0255(8) Uani 1 1 d . . .
C3 C 0.1484(3) 0.6520(3) 0.52045(14) 0.0213(8) Uani 1 1 d . . .
C4 C 0.2747(3) 0.6621(3) 0.48936(12) 0.0192(7) Uani 1 1 d . . .
C5 C 0.2810(4) 0.6603(4) 0.43378(14) 0.0256(8) Uani 1 1 d . . .
C6 C 0.1643(4) 0.6503(4) 0.41182(14) 0.0276(8) Uani 1 1 d . . .
C7 C 0.3986(3) 0.6723(3) 0.51489(12) 0.0192(7) Uani 1 1 d . . .
C8 C 0.3932(4) 0.6746(3) 0.57080(13) 0.0250(8) Uani 1 1 d . . .
C9 C 0.5098(4) 0.6836(4) 0.59287(14) 0.0262(8) Uani 1 1 d . . .
N10 N 0.6325(3) 0.6893(3) 0.56326(11) 0.0255(7) Uani 1 1 d . . .
C11 C 0.6387(4) 0.6876(3) 0.50950(14) 0.0254(8) Uani 1 1 d . . .
C12 C 0.5265(3) 0.6809(3) 0.48395(14) 0.0233(8) Uani 1 1 d . . .
N13 N 0.7062(3) 0.9776(3) 0.43797(11) 0.0263(7) Uani 1 1 d . . .
C14 C 0.7014(4) 0.9754(3) 0.49175(13) 0.0233(8) Uani 1 1 d . . .
C15 C 0.8121(4) 0.9829(3) 0.51749(14) 0.0241(8) Uani 1 1 d . . .
C16 C 0.9389(3) 0.9950(3) 0.48690(12) 0.0198(7) Uani 1 1 d . . .
C17 C 0.9439(4) 0.9987(3) 0.43112(13) 0.0250(8) Uani 1 1 d . . .
C18 C 0.8276(4) 0.9893(4) 0.40862(14) 0.0270(8) Uani 1 1 d . . .
O1A O 0.4988(3) -0.0457(2) 0.38386(9) 0.0299(6) Uani 1 1 d . . .
O2A O 0.5847(2) 0.0805(3) 0.31910(9) 0.0329(6) Uani 1 1 d . . .
C3A C 0.4981(3) 0.0187(3) 0.33527(12) 0.0224(8) Uani 1 1 d . . .
C4A C 0.3842(3) 0.0097(3) 0.30492(12) 0.0227(8) Uani 1 1 d . . .
C5A C 0.2932(4) -0.0666(4) 0.32801(14) 0.0254(8) Uani 1 1 d . . .
C6A C 0.1836(4) -0.0781(4) 0.30184(15) 0.0319(9) Uani 1 1 d . . .
C7A C 0.1632(4) -0.0104(4) 0.25190(14) 0.0307(9) Uani 1 1 d . . .
C8A C 0.2505(4) 0.0647(4) 0.22827(14) 0.0274(8) Uani 1 1 d . . .
C9A C 0.3647(3) 0.0740(3) 0.25333(13) 0.0235(8) Uani 1 1 d . . .
N10A N 0.4547(3) 0.1481(3) 0.22916(12) 0.0304(7) Uani 1 1 d . . .
C11A C 0.4766(3) 0.1906(3) 0.17458(12) 0.0240(8) Uani 1 1 d . . .
C12A C 0.4633(4) 0.1189(4) 0.13193(14) 0.0286(8) Uani 1 1 d . . .
C13A C 0.4898(4) 0.1634(4) 0.07920(14) 0.0307(9) Uani 1 1 d . . .
C14A C 0.5353(4) 0.2760(4) 0.06729(15) 0.0313(9) Uani 1 1 d . . .
C15A C 0.5544(3) 0.3454(4) 0.10879(13) 0.0254(8) Uani 1 1 d . . .
C16A C 0.5218(3) 0.3054(4) 0.16226(14) 0.0239(8) Uani 1 1 d . . .
C17A C 0.6195(4) 0.4578(4) 0.09538(14) 0.0322(9) Uani 1 1 d . . .
F18A F 0.7640(2) 0.4089(3) 0.08467(12) 0.0706(8) Uani 1 1 d . . .
F19A F 0.5933(3) 0.5413(3) 0.13500(9) 0.0668(8) Uani 1 1 d . . .
F20A F 0.5785(3) 0.5328(2) 0.05175(9) 0.0544(7) Uani 1 1 d . . .
O1B O 0.1603(3) 0.2912(2) 0.38060(9) 0.0307(6) Uani 1 1 d . . .
O2B O 0.2499(3) 0.4193(3) 0.31805(9) 0.0338(6) Uani 1 1 d . . .
C3B C 0.1629(3) 0.3572(4) 0.33215(13) 0.0244(8) Uani 1 1 d . . .
C4B C 0.0522(3) 0.3493(3) 0.30003(12) 0.0226(8) Uani 1 1 d . . .
C5B C -0.0425(4) 0.2761(4) 0.32092(14) 0.0262(8) Uani 1 1 d . . .
C6B C -0.1480(4) 0.2649(4) 0.29267(14) 0.0308(9) Uani 1 1 d . . .
C7B C -0.1625(4) 0.3322(4) 0.24242(14) 0.0300(9) Uani 1 1 d . . .
C8B C -0.0708(4) 0.4050(4) 0.22042(15) 0.0283(8) Uani 1 1 d . . .
C9B C 0.0404(3) 0.4138(3) 0.24770(13) 0.0246(8) Uani 1 1 d . . .
N10B N 0.1326(3) 0.4862(3) 0.22562(12) 0.0314(8) Uani 1 1 d . . .
C11B C 0.1556(3) 0.5341(4) 0.17173(13) 0.0277(8) Uani 1 1 d . . .
C12B C 0.1509(4) 0.4636(4) 0.12762(14) 0.0299(8) Uani 1 1 d . . .
C13B C 0.1771(4) 0.5138(4) 0.07541(15) 0.0359(9) Uani 1 1 d . . .
C14B C 0.2124(4) 0.6329(4) 0.06586(15) 0.0316(9) Uani 1 1 d . . .
C15B C 0.2230(4) 0.7016(4) 0.10924(13) 0.0278(8) Uani 1 1 d . A .
C16B C 0.1921(3) 0.6542(4) 0.16203(14) 0.0260(8) Uani 1 1 d . . .
C17B C 0.2706(4) 0.8245(4) 0.09973(15) 0.0361(9) Uani 1 1 d . . .
F18B F 0.3964(3) 0.8081(3) 0.11561(18) 0.1212(16) Uani 1 1 d . A 1
F19B F 0.1863(3) 0.9297(3) 0.12649(12) 0.0726(8) Uani 1 1 d . A 1
F20B F 0.2814(5) 0.8694(4) 0.04965(11) 0.1387(19) Uani 1 1 d . A 1
O1C O 0.8358(3) 0.6160(3) 0.38609(9) 0.0302(6) Uani 1 1 d . . .
O2C O 0.9245(3) 0.7437(3) 0.32301(9) 0.0352(6) Uani 1 1 d . . .
C3C C 0.8370(3) 0.6821(4) 0.33780(12) 0.0236(8) Uani 1 1 d . . .
C4C C 0.7247(3) 0.6746(3) 0.30630(12) 0.0225(7) Uani 1 1 d . . .
C5C C 0.6303(4) 0.6018(4) 0.32764(14) 0.0258(8) Uani 1 1 d . . .
C6C C 0.5223(4) 0.5925(4) 0.30020(14) 0.0300(9) Uani 1 1 d . . .
C7C C 0.5072(4) 0.6603(4) 0.25011(14) 0.0298(9) Uani 1 1 d . . .
C8C C 0.5978(4) 0.7325(4) 0.22756(15) 0.0298(8) Uani 1 1 d . . .
C9C C 0.7113(3) 0.7401(3) 0.25409(12) 0.0238(8) Uani 1 1 d . . .
N10C N 0.8038(3) 0.8117(3) 0.23167(12) 0.0329(8) Uani 1 1 d . . .
C11C C 0.8166(3) 0.8704(4) 0.17868(13) 0.0272(8) Uani 1 1 d . . .
C12C C 0.8389(4) 0.9969(4) 0.17201(16) 0.0315(9) Uani 1 1 d . . .
C13C C 0.8608(4) 1.0567(4) 0.12129(16) 0.0384(10) Uani 1 1 d . . .
C14C C 0.8582(4) 0.9900(4) 0.07550(16) 0.0382(10) Uani 1 1 d . . .
C15C C 0.8351(4) 0.8647(4) 0.08217(14) 0.0334(9) Uani 1 1 d . . .
C16C C 0.8153(4) 0.8033(4) 0.13338(14) 0.0307(9) Uani 1 1 d . . .
F17C F 0.8471(3) 0.6646(3) 0.04217(9) 0.0711(8) Uani 1 1 d . . .
F18C F 0.7001(3) 0.8477(4) 0.01604(12) 0.1028(12) Uani 1 1 d . . .
F19C F 0.9250(4) 0.8075(3) -0.00750(10) 0.0885(10) 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
N1 C2 1.332(4) . ?
N1 C6 1.332(4) . ?
C1 F17C 1.318(5) . ?
C1 F18C 1.325(5) . ?
C1 F19C 1.331(4) . ?
C1 C15C 1.476(6) . ?
C2 C3 1.381(5) . ?
C2 H2 0.94(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.94(4) . ?
C4 C5 1.383(4) . ?
C4 C7 1.493(4) . ?
C5 C6 1.379(5) . ?
C5 H5 0.96(3) . ?
C6 H6 0.91(3) . ?
C7 C8 1.392(4) . ?
C7 C12 1.396(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.97(3) . ?
C9 N10 1.331(4) . ?
C9 H9 0.98(3) . ?
N10 C11 1.337(4) . ?
C11 C12 1.378(5) . ?
C11 H11 0.97(3) . ?
C12 H12 0.92(3) . ?
N13 C14 1.336(4) . ?
N13 C18 1.337(4) . ?
C14 C15 1.370(5) . ?
C14 H14 0.94(3) . ?
C15 C16 1.396(4) . ?
C15 H15 0.93(3) . ?
C16 C17 1.385(4) . ?
C16 C16 1.486(6) 2_776 ?
C17 C18 1.381(5) . ?
C17 H17 1.00(3) . ?
C18 H18 0.91(4) . ?
O1A C3A 1.331(4) . ?
O1A H1A 0.93(5) . ?
O2A C3A 1.220(4) . ?
C3A C4A 1.474(4) . ?
C4A C5A 1.401(4) . ?
C4A C9A 1.407(4) . ?
C5A C6A 1.382(5) . ?
C5A H5A 0.98(3) . ?
C6A C7A 1.385(5) . ?
C6A H6A 0.92(4) . ?
C7A C8A 1.368(5) . ?
C7A H7A 0.93(3) . ?
C8A C9A 1.398(5) . ?
C8A H8A 0.97(4) . ?
C9A N10A 1.385(4) . ?
N10A C11A 1.400(4) . ?
N10A H10A 0.87(4) . ?
C11A C16A 1.392(5) . ?
C11A C12A 1.399(5) . ?
C12A C13A 1.370(5) . ?
C12A H12A 0.93(3) . ?
C13A C14A 1.370(5) . ?
C13A H13A 1.00(3) . ?
C14A C15A 1.382(5) . ?
C14A H14A 0.82(3) . ?
C15A C16A 1.382(4) . ?
C15A C17A 1.488(5) . ?
C16A H16A 0.93(3) . ?
C17A F20A 1.318(4) . ?
C17A F19A 1.320(4) . ?
C17A F18A 1.345(4) . ?
O1B C3B 1.336(4) . ?
O1B H1B 0.94(5) . ?
O2B C3B 1.218(4) . ?
C3B C4B 1.472(4) . ?
C4B C5B 1.393(4) . ?
C4B C9B 1.417(4) . ?
C5B C6B 1.378(5) . ?
C5B H5B 0.92(4) . ?
C6B C7B 1.384(5) . ?
C6B H6B 0.95(3) . ?
C7B C8B 1.373(5) . ?
C7B H7B 0.99(4) . ?
C8B C9B 1.402(5) . ?
C8B H8B 0.92(3) . ?
C9B N10B 1.375(4) . ?
N10B C11B 1.402(4) . ?
N10B H10B 0.87(4) . ?
C11B C12B 1.392(5) . ?
C11B C16B 1.393(5) . ?
C12B C13B 1.377(5) . ?
C12B H12B 0.94(3) . ?
C13B C14B 1.377(5) . ?
C13B H13B 1.08(3) . ?
C14B C15B 1.385(5) . ?
C14B H14B 0.89(4) . ?
C15B C16B 1.388(5) . ?
C15B C17B 1.479(5) . ?
C16B H16B 0.95(4) . ?
C17B F20B 1.295(4) . ?
C17B F18B 1.311(4) . ?
C17B F19B 1.315(4) . ?
O1C C3C 1.332(4) . ?
O1C H1C 0.88(4) . ?
O2C C3C 1.221(4) . ?
C3C C4C 1.474(4) . ?
C4C C5C 1.390(4) . ?
C4C C9C 1.419(4) . ?
C5C C6C 1.378(5) . ?
C5C H5C 0.93(4) . ?
C6C C7C 1.383(5) . ?
C6C H6C 0.93(3) . ?
C7C C8C 1.363(5) . ?
C7C H7C 0.99(3) . ?
C8C C9C 1.407(5) . ?
C8C H8C 0.90(3) . ?
C9C N10C 1.373(4) . ?
N10C C11C 1.410(4) . ?
N10C H10C 0.83(4) . ?
C11C C16C 1.387(5) . ?
C11C C12C 1.389(5) . ?
C12C C13C 1.377(5) . ?
C12C H12C 0.98(4) . ?
C13C C14C 1.398(6) . ?
C13C H13C 1.13(4) . ?
C14C C15C 1.381(5) . ?
C14C H14C 1.02(3) . ?
C15C C16C 1.391(5) . ?
C16C H16C 0.99(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
C2 N1 C6 116.6(3) . . ?
F17C C1 F18C 106.2(4) . . ?
F17C C1 F19C 105.0(4) . . ?
F18C C1 F19C 105.8(3) . . ?
F17C C1 C15C 114.5(3) . . ?
F18C C1 C15C 111.8(4) . . ?
F19C C1 C15C 112.9(3) . . ?
N1 C2 C3 123.8(3) . . ?
N1 C2 H2 117.4(19) . . ?
C3 C2 H2 118.7(19) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 118(2) . . ?
C4 C3 H3 123(2) . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C7 121.6(3) . . ?
C3 C4 C7 121.5(3) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 119(2) . . ?
C4 C5 H5 121(2) . . ?
N1 C6 C5 123.6(3) . . ?
N1 C6 H6 114.8(19) . . ?
C5 C6 H6 121.6(19) . . ?
C8 C7 C12 116.2(3) . . ?
C8 C7 C4 122.0(3) . . ?
C12 C7 C4 121.8(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 117.5(19) . . ?
C7 C8 H8 122.1(19) . . ?
N10 C9 C8 123.3(3) . . ?
N10 C9 H9 116.4(17) . . ?
C8 C9 H9 120.4(17) . . ?
C9 N10 C11 116.8(3) . . ?
N10 C11 C12 123.8(3) . . ?
N10 C11 H11 113.5(19) . . ?
C12 C11 H11 122.6(19) . . ?
C11 C12 C7 119.6(3) . . ?
C11 C12 H12 119.8(18) . . ?
C7 C12 H12 120.6(18) . . ?
C14 N13 C18 116.3(3) . . ?
N13 C14 C15 124.1(3) . . ?
N13 C14 H14 116.5(18) . . ?
C15 C14 H14 119.4(18) . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 119(2) . . ?
C16 C15 H15 121(2) . . ?
C17 C16 C15 116.5(3) . . ?
C17 C16 C16 122.1(3) . 2_776 ?
C15 C16 C16 121.5(4) . 2_776 ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 119.0(19) . . ?
C16 C17 H17 120.9(19) . . ?
N13 C18 C17 123.5(3) . . ?
N13 C18 H18 116(2) . . ?
C17 C18 H18 120(2) . . ?
C3A O1A H1A 113(3) . . ?
O2A C3A O1A 121.1(3) . . ?
O2A C3A C4A 124.8(3) . . ?
O1A C3A C4A 114.1(3) . . ?
C5A C4A C9A 118.9(3) . . ?
C5A C4A C3A 118.9(3) . . ?
C9A C4A C3A 122.2(3) . . ?
C6A C5A C4A 121.7(3) . . ?
C6A C5A H5A 119.5(19) . . ?
C4A C5A H5A 118.7(19) . . ?
C5A C6A C7A 118.5(3) . . ?
C5A C6A H6A 118(2) . . ?
C7A C6A H6A 123(2) . . ?
C8A C7A C6A 121.2(3) . . ?
C8A C7A H7A 117(2) . . ?
C6A C7A H7A 121(2) . . ?
C7A C8A C9A 121.2(3) . . ?
C7A C8A H8A 119(2) . . ?
C9A C8A H8A 120(2) . . ?
N10A C9A C8A 121.4(3) . . ?
N10A C9A C4A 120.1(3) . . ?
C8A C9A C4A 118.5(3) . . ?
C9A N10A C11A 128.3(3) . . ?
C9A N10A H10A 111(2) . . ?
C11A N10A H10A 120(2) . . ?
C16A C11A C12A 118.6(3) . . ?
C16A C11A N10A 118.1(3) . . ?
C12A C11A N10A 123.2(3) . . ?
C13A C12A C11A 120.6(3) . . ?
C13A C12A H12A 119.4(19) . . ?
C11A C12A H12A 119.8(19) . . ?
C12A C13A C14A 120.5(4) . . ?
C12A C13A H13A 119.5(16) . . ?
C14A C13A H13A 119.9(16) . . ?
C13A C14A C15A 119.8(3) . . ?
C13A C14A H14A 121(2) . . ?
C15A C14A H14A 119(2) . . ?
C16A C15A C14A 120.4(3) . . ?
C16A C15A C17A 120.2(3) . . ?
C14A C15A C17A 119.3(3) . . ?
C15A C16A C11A 120.0(3) . . ?
C15A C16A H16A 120.5(19) . . ?
C11A C16A H16A 119.5(19) . . ?
F20A C17A F19A 106.9(3) . . ?
F20A C17A F18A 104.7(3) . . ?
F19A C17A F18A 106.0(3) . . ?
F20A C17A C15A 114.0(3) . . ?
F19A C17A C15A 113.6(3) . . ?
F18A C17A C15A 110.9(3) . . ?
C3B O1B H1B 115(3) . . ?
O2B C3B O1B 120.6(3) . . ?
O2B C3B C4B 125.2(3) . . ?
O1B C3B C4B 114.3(3) . . ?
C5B C4B C9B 118.8(3) . . ?
C5B C4B C3B 119.8(3) . . ?
C9B C4B C3B 121.4(3) . . ?
C6B C5B C4B 122.4(3) . . ?
C6B C5B H5B 119(2) . . ?
C4B C5B H5B 118(2) . . ?
C5B C6B C7B 118.5(3) . . ?
C5B C6B H6B 121.7(18) . . ?
C7B C6B H6B 119.8(18) . . ?
C8B C7B C6B 120.8(3) . . ?
C8B C7B H7B 118(2) . . ?
C6B C7B H7B 122(2) . . ?
C7B C8B C9B 121.6(3) . . ?
C7B C8B H8B 117(2) . . ?
C9B C8B H8B 122(2) . . ?
N10B C9B C8B 121.6(3) . . ?
N10B C9B C4B 120.4(3) . . ?
C8B C9B C4B 117.9(3) . . ?
C9B N10B C11B 128.2(3) . . ?
C9B N10B H10B 113(3) . . ?
C11B N10B H10B 119(3) . . ?
C12B C11B C16B 118.7(3) . . ?
C12B C11B N10B 123.0(3) . . ?
C16B C11B N10B 118.2(3) . . ?
C13B C12B C11B 120.7(4) . . ?
C13B C12B H12B 122(2) . . ?
C11B C12B H12B 117(2) . . ?
C14B C13B C12B 120.5(4) . . ?
C14B C13B H13B 119.5(17) . . ?
C12B C13B H13B 120.0(17) . . ?
C13B C14B C15B 119.5(3) . . ?
C13B C14B H14B 120(2) . . ?
C15B C14B H14B 121(2) . . ?
C14B C15B C16B 120.4(3) . . ?
C14B C15B C17B 120.2(3) . . ?
C16B C15B C17B 119.3(3) . . ?
C15B C16B C11B 120.1(3) . . ?
C15B C16B H16B 123(2) . . ?
C11B C16B H16B 116(2) . . ?
F20B C17B F18B 105.7(4) . . ?
F20B C17B F19B 104.7(4) . . ?
F18B C17B F19B 102.5(4) . . ?
F20B C17B C15B 114.7(3) . . ?
F18B C17B C15B 113.4(3) . . ?
F19B C17B C15B 114.6(3) . . ?
C3C O1C H1C 114(3) . . ?
O2C C3C O1C 120.7(3) . . ?
O2C C3C C4C 125.1(3) . . ?
O1C C3C C4C 114.2(3) . . ?
C5C C4C C9C 119.0(3) . . ?
C5C C4C C3C 119.9(3) . . ?
C9C C4C C3C 121.1(3) . . ?
C6C C5C C4C 122.3(3) . . ?
C6C C5C H5C 120(2) . . ?
C4C C5C H5C 118(2) . . ?
C5C C6C C7C 118.2(3) . . ?
C5C C6C H6C 119(2) . . ?
C7C C6C H6C 123(2) . . ?
C8C C7C C6C 121.4(3) . . ?
C8C C7C H7C 116.1(17) . . ?
C6C C7C H7C 122.4(17) . . ?
C7C C8C C9C 121.4(3) . . ?
C7C C8C H8C 120(2) . . ?
C9C C8C H8C 118(2) . . ?
N10C C9C C8C 121.9(3) . . ?
N10C C9C C4C 120.4(3) . . ?
C8C C9C C4C 117.6(3) . . ?
C9C N10C C11C 128.2(3) . . ?
C9C N10C H10C 115(3) . . ?
C11C N10C H10C 117(3) . . ?
C16C C11C C12C 119.4(3) . . ?
C16C C11C N10C 122.3(3) . . ?
C12C C11C N10C 118.2(3) . . ?
C13C C12C C11C 121.3(4) . . ?
C13C C12C H12C 121(2) . . ?
C11C C12C H12C 118(2) . . ?
C12C C13C C14C 119.5(4) . . ?
C12C C13C H13C 121.8(19) . . ?
C14C C13C H13C 118.4(19) . . ?
C15C C14C C13C 119.2(3) . . ?
C15C C14C H14C 123(2) . . ?
C13C C14C H14C 118(2) . . ?
C14C C15C C16C 121.4(4) . . ?
C14C C15C C1 119.4(3) . . ?
C16C C15C C1 119.2(4) . . ?
C11C C16C C15C 119.2(4) . . ?
C11C C16C H16C 122.8(17) . . ?
C15C C16C H16C 117.9(18) . . ?

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
C6 N1 C2 C3 -0.6(5) . . . . ?
N1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C2 C3 C4 C7 -180.0(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C7 C4 C5 C6 179.8(3) . . . . ?
C2 N1 C6 C5 0.3(5) . . . . ?
C4 C5 C6 N1 -0.4(5) . . . . ?
C5 C4 C7 C8 179.8(3) . . . . ?
C3 C4 C7 C8 -1.2(5) . . . . ?
C5 C4 C7 C12 0.3(5) . . . . ?
C3 C4 C7 C12 179.2(3) . . . . ?
C12 C7 C8 C9 -0.6(5) . . . . ?
C4 C7 C8 C9 179.8(3) . . . . ?
C7 C8 C9 N10 -0.7(5) . . . . ?
C8 C9 N10 C11 0.9(5) . . . . ?
C9 N10 C11 C12 0.2(5) . . . . ?
N10 C11 C12 C7 -1.5(5) . . . . ?
C8 C7 C12 C11 1.6(5) . . . . ?
C4 C7 C12 C11 -178.8(3) . . . . ?
C18 N13 C14 C15 -0.7(5) . . . . ?
N13 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C14 C15 C16 C16 179.3(4) . . . 2_776 ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C16 C17 C18 -179.9(4) 2_776 . . . ?
C14 N13 C18 C17 0.1(5) . . . . ?
C16 C17 C18 N13 0.6(5) . . . . ?
O2A C3A C4A C5A 179.0(3) . . . . ?
O1A C3A C4A C5A -2.1(4) . . . . ?
O2A C3A C4A C9A -0.3(5) . . . . ?
O1A C3A C4A C9A 178.6(3) . . . . ?
C9A C4A C5A C6A -1.1(5) . . . . ?
C3A C4A C5A C6A 179.5(3) . . . . ?
C4A C5A C6A C7A -1.0(5) . . . . ?
C5A C6A C7A C8A 1.1(6) . . . . ?
C6A C7A C8A C9A 0.9(6) . . . . ?
C7A C8A C9A N10A 178.9(3) . . . . ?
C7A C8A C9A C4A -3.0(5) . . . . ?
C5A C4A C9A N10A -178.9(3) . . . . ?
C3A C4A C9A N10A 0.5(5) . . . . ?
C5A C4A C9A C8A 3.1(5) . . . . ?
C3A C4A C9A C8A -177.6(3) . . . . ?
C8A C9A N10A C11A -19.1(5) . . . . ?
C4A C9A N10A C11A 162.9(3) . . . . ?
C9A N10A C11A C16A 154.2(3) . . . . ?
C9A N10A C11A C12A -29.7(5) . . . . ?
C16A C11A C12A C13A -2.0(5) . . . . ?
N10A C11A C12A C13A -178.2(3) . . . . ?
C11A C12A C13A C14A 2.5(5) . . . . ?
C12A C13A C14A C15A 0.0(5) . . . . ?
C13A C14A C15A C16A -2.9(5) . . . . ?
C13A C14A C15A C17A 173.1(3) . . . . ?
C14A C15A C16A C11A 3.3(5) . . . . ?
C17A C15A C16A C11A -172.6(3) . . . . ?
C12A C11A C16A C15A -0.9(5) . . . . ?
N10A C11A C16A C15A 175.5(3) . . . . ?
C16A C15A C17A F20A -146.1(3) . . . . ?
C14A C15A C17A F20A 37.9(5) . . . . ?
C16A C15A C17A F19A -23.3(5) . . . . ?
C14A C15A C17A F19A 160.7(3) . . . . ?
C16A C15A C17A F18A 96.0(4) . . . . ?
C14A C15A C17A F18A -80.0(4) . . . . ?
O2B C3B C4B C5B -179.2(3) . . . . ?
O1B C3B C4B C5B -0.6(5) . . . . ?
O2B C3B C4B C9B 1.4(5) . . . . ?
O1B C3B C4B C9B -180.0(3) . . . . ?
C9B C4B C5B C6B -0.5(5) . . . . ?
C3B C4B C5B C6B -179.8(3) . . . . ?
C4B C5B C6B C7B -1.9(5) . . . . ?
C5B C6B C7B C8B 2.0(5) . . . . ?
C6B C7B C8B C9B 0.2(6) . . . . ?
C7B C8B C9B N10B 179.7(3) . . . . ?
C7B C8B C9B C4B -2.5(5) . . . . ?
C5B C4B C9B N10B -179.6(3) . . . . ?
C3B C4B C9B N10B -0.2(5) . . . . ?
C5B C4B C9B C8B 2.6(5) . . . . ?
C3B C4B C9B C8B -178.1(3) . . . . ?
C8B C9B N10B C11B -15.5(6) . . . . ?
C4B C9B N10B C11B 166.8(3) . . . . ?
C9B N10B C11B C12B -35.0(5) . . . . ?
C9B N10B C11B C16B 148.5(4) . . . . ?
C16B C11B C12B C13B -2.2(5) . . . . ?
N10B C11B C12B C13B -178.7(3) . . . . ?
C11B C12B C13B C14B 1.9(6) . . . . ?
C12B C13B C14B C15B 0.7(6) . . . . ?
C13B C14B C15B C16B -2.8(5) . . . . ?
C13B C14B C15B C17B 175.7(3) . . . . ?
C14B C15B C16B C11B 2.5(5) . . . . ?
C17B C15B C16B C11B -176.1(3) . . . . ?
C12B C11B C16B C15B 0.0(5) . . . . ?
N10B C11B C16B C15B 176.7(3) . . . . ?
C14B C15B C17B F20B 8.7(6) . . . . ?
C16B C15B C17B F20B -172.7(4) . . . . ?
C14B C15B C17B F18B -113.0(4) . . . . ?
C16B C15B C17B F18B 65.6(5) . . . . ?
C14B C15B C17B F19B 129.8(4) . . . . ?
C16B C15B C17B F19B -51.6(5) . . . . ?
O2C C3C C4C C5C -179.6(3) . . . . ?
O1C C3C C4C C5C -0.6(5) . . . . ?
O2C C3C C4C C9C 0.8(5) . . . . ?
O1C C3C C4C C9C 179.8(3) . . . . ?
C9C C4C C5C C6C -1.0(5) . . . . ?
C3C C4C C5C C6C 179.3(3) . . . . ?
C4C C5C C6C C7C -1.0(5) . . . . ?
C5C C6C C7C C8C 1.3(6) . . . . ?
C6C C7C C8C C9C 0.6(6) . . . . ?
C7C C8C C9C N10C 179.6(3) . . . . ?
C7C C8C C9C C4C -2.6(5) . . . . ?
C5C C4C C9C N10C -179.4(3) . . . . ?
C3C C4C C9C N10C 0.3(5) . . . . ?
C5C C4C C9C C8C 2.8(5) . . . . ?
C3C C4C C9C C8C -177.6(3) . . . . ?
C8C C9C N10C C11C -9.7(6) . . . . ?
C4C C9C N10C C11C 172.6(3) . . . . ?
C9C N10C C11C C16C -43.1(5) . . . . ?
C9C N10C C11C C12C 140.2(4) . . . . ?
C16C C11C C12C C13C -0.6(5) . . . . ?
N10C C11C C12C C13C 176.2(3) . . . . ?
C11C C12C C13C C14C 1.1(5) . . . . ?
C12C C13C C14C C15C -0.7(5) . . . . ?
C13C C14C C15C C16C -0.4(5) . . . . ?
C13C C14C C15C C1 177.8(3) . . . . ?
F17C C1 C15C C14C 161.1(3) . . . . ?
F18C C1 C15C C14C -78.1(5) . . . . ?
F19C C1 C15C C14C 41.1(5) . . . . ?
F17C C1 C15C C16C -20.7(5) . . . . ?
F18C C1 C15C C16C 100.1(4) . . . . ?
F19C C1 C15C C16C -140.7(4) . . . . ?
C12C C11C C16C C15C -0.5(5) . . . . ?
N10C C11C C16C C15C -177.1(3) . . . . ?
C14C C15C C16C C11C 0.9(5) . . . . ?
C1 C15C C16C C11C -177.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_c:\xrd\mef44b~1\final\p13ccw81
_database_code_depnum_ccdc_archive 'CCDC 1018668'
_audit_update_record             
;
2014-08-10 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"2-(2,3-dimethylphenyl)aminobenzoic acid and 4,4'bipyridine complex"
_chemical_name_common            
;
mefenamic acid and 4,4'-Bipyridine complex
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N1 O2, 0.5(C10 H8 N2)'
_chemical_formula_sum            'C20 H19 N2 O2'
_chemical_formula_weight         319.37

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'
O O 0.0106 0.0060 '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'

_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                   7.3086(3)
_cell_length_b                   8.6692(4)
_cell_length_c                   13.6320(5)
_cell_angle_alpha                106.135(4)
_cell_angle_beta                 99.428(4)
_cell_angle_gamma                98.758(4)
_cell_volume                     800.46(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5336
_cell_measurement_theta_min      2.8830
_cell_measurement_theta_max      29.5773

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17917
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         29.64
_reflns_number_total             4011
_reflns_number_gt                2899
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0457P)²+0.1998P] 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         4011
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15336(16) 0.75893(14) 0.40874(8) 0.0378(3) Uani 1 1 d . . .
N1 N 0.30610(19) 0.07981(16) 0.45943(10) 0.0363(3) Uani 1 1 d . . .
H1 H 0.206(3) 0.875(3) 0.4270(17) 0.077(7) Uiso 1 1 d . . .
O2 O 0.26994(16) 0.75237(12) 0.26775(8) 0.0378(3) Uani 1 1 d . . .
C3 C 0.1896(2) 0.67917(18) 0.31838(11) 0.0282(3) Uani 1 1 d . . .
C4 C 0.12566(19) 0.49980(17) 0.28557(10) 0.0260(3) Uani 1 1 d . . .
C5 C 0.0333(2) 0.4262(2) 0.34845(12) 0.0322(3) Uani 1 1 d . . .
H5 H 0.014(2) 0.4985(19) 0.4134(13) 0.033(4) Uiso 1 1 d . . .
H12 H 0.075(2) 0.411(2) -0.0648(12) 0.036(4) Uiso 1 1 d . . .
H10 H 0.283(3) 0.574(2) 0.1484(14) 0.046(5) Uiso 1 1 d . . .
H17B H 0.539(3) 0.392(2) 0.2006(16) 0.058(6) Uiso 1 1 d . . .
H23 H 0.414(2) 0.037(2) 0.3368(14) 0.049(5) Uiso 1 1 d . . .
H18C H 0.670(2) 0.066(2) -0.0092(14) 0.045(5) Uiso 1 1 d . . .
H18B H 0.793(3) 0.230(2) -0.0138(14) 0.053(5) Uiso 1 1 d . . .
H6 H -0.088(2) 0.211(2) 0.3659(14) 0.045(5) Uiso 1 1 d . . .
H20 H 0.338(3) 0.438(2) 0.6171(14) 0.051(5) Uiso 1 1 d . . .
H19 H 0.213(3) 0.162(2) 0.5880(15) 0.055(5) Uiso 1 1 d . . .
H17A H 0.708(3) 0.347(2) 0.1472(14) 0.056(6) Uiso 1 1 d . . .
H17C H 0.562(3) 0.208(3) 0.1579(15) 0.060(6) Uiso 1 1 d . . .
H22 H 0.555(3) 0.312(2) 0.3553(15) 0.054(5) Uiso 1 1 d . . .
C6 C -0.0251(2) 0.2588(2) 0.32180(13) 0.0379(4) Uani 1 1 d . . .
C7 C 0.0085(2) 0.1609(2) 0.23017(13) 0.0366(4) Uani 1 1 d . . .
H7 H -0.029(2) 0.043(2) 0.2085(12) 0.037(4) Uiso 1 1 d . . .
H13 H 0.155(2) 0.2697(19) -0.2210(13) 0.037(4) Uiso 1 1 d . . .
C8 C 0.0976(2) 0.22832(18) 0.16587(12) 0.0302(3) Uani 1 1 d . . .
H8 H 0.120(2) 0.156(2) 0.1019(13) 0.035(4) Uiso 1 1 d . . .
C9 C 0.15840(19) 0.39887(16) 0.19121(10) 0.0250(3) Uani 1 1 d . . .
N10 N 0.24471(18) 0.46465(15) 0.12594(9) 0.0289(3) Uani 1 1 d . . .
C11 C 0.2941(2) 0.37161(16) 0.03364(10) 0.0248(3) Uani 1 1 d . . .
C12 C 0.1846(2) 0.35991(17) -0.06243(11) 0.0278(3) Uani 1 1 d . . .
C13 C 0.2332(2) 0.27747(18) -0.15358(11) 0.0301(3) Uani 1 1 d . . .
C14 C 0.3894(2) 0.20628(17) -0.14846(11) 0.0274(3) Uani 1 1 d . . .
H14 H 0.424(2) 0.1473(19) -0.2135(12) 0.034(4) Uiso 1 1 d . . .
H18A H 0.686(2) 0.085(2) -0.1217(14) 0.046(5) Uiso 1 1 d . . .
C15 C 0.50086(19) 0.21647(16) -0.05306(11) 0.0250(3) Uani 1 1 d . . .
C16 C 0.4528(2) 0.30041(16) 0.04002(10) 0.0248(3) Uani 1 1 d . . .
C17 C 0.5719(2) 0.3135(2) 0.14361(12) 0.0336(3) Uani 1 1 d . . .
C18 C 0.6737(2) 0.1424(2) -0.04983(13) 0.0333(3) Uani 1 1 d . . .
C19 C 0.2864(3) 0.1982(2) 0.54063(13) 0.0413(4) Uani 1 1 d . . .
C20 C 0.3594(2) 0.3614(2) 0.55962(12) 0.0384(4) Uani 1 1 d . . .
C21 C 0.4611(2) 0.41203(18) 0.49233(11) 0.0298(3) Uani 1 1 d . . .
C22 C 0.4836(3) 0.2878(2) 0.40858(12) 0.0398(4) Uani 1 1 d . . .
C23 C 0.4058(3) 0.1280(2) 0.39519(13) 0.0402(4) 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
O1 C3 1.3248(16) . ?
O1 H1 0.97(2) . ?
N1 C19 1.328(2) . ?
N1 C23 1.339(2) . ?
O2 C3 1.2191(17) . ?
C3 C4 1.470(2) . ?
C4 C5 1.4002(19) . ?
C4 C9 1.4200(19) . ?
C5 C6 1.374(2) . ?
C5 H5 0.976(16) . ?
C6 C7 1.384(2) . ?
C6 H6 0.957(18) . ?
C7 C8 1.375(2) . ?
C7 H7 0.961(17) . ?
C8 C9 1.403(2) . ?
C8 H8 0.977(17) . ?
C9 N10 1.3679(17) . ?
N10 C11 1.4274(17) . ?
N10 H10 0.891(19) . ?
C11 C12 1.387(2) . ?
C11 C16 1.3962(19) . ?
C12 C13 1.382(2) . ?
C12 H12 0.974(17) . ?
C13 C14 1.379(2) . ?
C13 H13 0.979(17) . ?
C14 C15 1.389(2) . ?
C14 H14 0.985(16) . ?
C15 C16 1.4048(19) . ?
C15 C18 1.502(2) . ?
C16 C17 1.498(2) . ?
C17 H17B 0.97(2) . ?
C17 H17A 0.98(2) . ?
C17 H17C 0.98(2) . ?
C18 H18C 0.974(18) . ?
C18 H18B 1.01(2) . ?
C18 H18A 0.995(18) . ?
C19 C20 1.370(2) . ?
C19 H19 0.990(19) . ?
C20 C21 1.391(2) . ?
C20 H20 0.929(19) . ?
C21 C22 1.386(2) . ?
C21 C21 1.488(3) 2_666 ?
C22 C23 1.365(2) . ?
C22 H22 1.012(19) . ?
C23 H23 0.971(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 110.3(13) . . ?
C19 N1 C23 116.07(14) . . ?
O2 C3 O1 121.18(13) . . ?
O2 C3 C4 123.83(12) . . ?
O1 C3 C4 114.99(12) . . ?
C5 C4 C9 119.14(13) . . ?
C5 C4 C3 119.93(13) . . ?
C9 C4 C3 120.93(12) . . ?
C6 C5 C4 121.79(15) . . ?
C6 C5 H5 120.9(9) . . ?
C4 C5 H5 117.3(9) . . ?
C5 C6 C7 118.84(14) . . ?
C5 C6 H6 120.5(10) . . ?
C7 C6 H6 120.7(10) . . ?
C8 C7 C6 121.20(15) . . ?
C8 C7 H7 117.0(10) . . ?
C6 C7 H7 121.8(10) . . ?
C7 C8 C9 121.08(14) . . ?
C7 C8 H8 119.4(9) . . ?
C9 C8 H8 119.5(9) . . ?
N10 C9 C8 120.55(13) . . ?
N10 C9 C4 121.51(12) . . ?
C8 C9 C4 117.94(12) . . ?
C9 N10 C11 124.86(11) . . ?
C9 N10 H10 115.4(11) . . ?
C11 N10 H10 119.4(11) . . ?
C12 C11 C16 121.06(13) . . ?
C12 C11 N10 118.07(12) . . ?
C16 C11 N10 120.82(12) . . ?
C13 C12 C11 119.79(14) . . ?
C13 C12 H12 120.7(9) . . ?
C11 C12 H12 119.5(9) . . ?
C14 C13 C12 119.78(14) . . ?
C14 C13 H13 121.0(10) . . ?
C12 C13 H13 119.2(10) . . ?
C13 C14 C15 121.35(13) . . ?
C13 C14 H14 119.7(9) . . ?
C15 C14 H14 118.9(9) . . ?
C14 C15 C16 119.26(13) . . ?
C14 C15 C18 120.18(13) . . ?
C16 C15 C18 120.54(13) . . ?
C11 C16 C15 118.76(13) . . ?
C11 C16 C17 121.20(13) . . ?
C15 C16 C17 120.04(13) . . ?
C16 C17 H17B 111.3(12) . . ?
C16 C17 H17A 112.4(11) . . ?
H17B C17 H17A 107.9(16) . . ?
C16 C17 H17C 112.9(11) . . ?
H17B C17 H17C 108.7(16) . . ?
H17A C17 H17C 103.3(16) . . ?
C15 C18 H18C 111.5(10) . . ?
C15 C18 H18B 111.0(11) . . ?
H18C C18 H18B 105.5(15) . . ?
C15 C18 H18A 110.9(10) . . ?
H18C C18 H18A 109.4(14) . . ?
H18B C18 H18A 108.4(14) . . ?
N1 C19 C20 123.72(16) . . ?
N1 C19 H19 115.6(11) . . ?
C20 C19 H19 120.7(11) . . ?
C19 C20 C21 120.33(14) . . ?
C19 C20 H20 119.4(12) . . ?
C21 C20 H20 120.2(12) . . ?
C22 C21 C20 115.72(15) . . ?
C22 C21 C21 121.74(17) . 2_666 ?
C20 C21 C21 122.53(16) . 2_666 ?
C23 C22 C21 120.23(15) . . ?
C23 C22 H22 118.0(11) . . ?
C21 C22 H22 121.7(11) . . ?
N1 C23 C22 123.92(14) . . ?
N1 C23 H23 112.6(11) . . ?
C22 C23 H23 123.5(11) . . ?

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_c:\xrd\tolf44~1\final\p21c
_database_code_depnum_ccdc_archive 'CCDC 1018669'
_audit_update_record             
;
2014-08-10 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"2-[(3-chloro-2-methylphenyl)amino]benzoic acid and4,4'bipyridine complex"
_chemical_name_common            
;
tolfenamic acid and 4,4'-Bipyridine complex
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cl1 N1 O2, 0.5(C10 H8 N2)'
_chemical_formula_sum            'C19 H16 Cl N2 O2'
_chemical_formula_weight         339.79

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   4.7081(2)
_cell_length_b                   45.2195(14)
_cell_length_c                   7.9188(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.896(5)
_cell_angle_gamma                90.00
_cell_volume                     1613.12(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3350
_cell_measurement_theta_min      3.2270
_cell_measurement_theta_max      26.4850

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97881
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11680
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3267
_reflns_number_gt                2460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0284P)²+0.7578P] 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         3267
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.4933(5) 0.43892(4) 0.5535(3) 0.0535(5) Uani 1 1 d . . .
H1 H 1.552(7) 0.4489(7) 0.467(4) 0.085(11) Uiso 1 1 d . . .
O2 O 1.3620(4) 0.40536(3) 0.3403(2) 0.0443(4) Uani 1 1 d . . .
N2 N 1.6878(5) 0.46727(4) 0.3122(3) 0.0505(6) Uani 1 1 d . . .
C3 C 1.3656(6) 0.41356(5) 0.4878(3) 0.0380(6) Uani 1 1 d . . .
C4 C 1.2271(5) 0.39734(5) 0.6045(3) 0.0341(5) Uani 1 1 d . . .
C5 C 1.2537(6) 0.40774(6) 0.7751(3) 0.0444(6) Uani 1 1 d . . .
H5 H 1.373(5) 0.4241(5) 0.810(3) 0.039(7) Uiso 1 1 d . . .
H17A H 1.355(6) 0.2866(6) 0.484(4) 0.064(9) Uiso 1 1 d . . .
H13 H 0.262(5) 0.3193(4) -0.010(3) 0.032(6) Uiso 1 1 d . . .
H7 H 0.842(6) 0.3610(5) 0.898(3) 0.052(8) Uiso 1 1 d . . .
H17C H 1.178(7) 0.2905(6) 0.617(4) 0.080(10) Uiso 1 1 d . . .
H19 H 1.677(7) 0.5074(6) 0.401(4) 0.075(9) Uiso 1 1 d . . .
H22 H 1.908(7) 0.4515(6) -0.024(4) 0.074(10) Uiso 1 1 d . . .
H23 H 1.715(6) 0.4310(6) 0.184(4) 0.067(9) Uiso 1 1 d . . .
C6 C 1.1182(7) 0.39408(6) 0.8844(3) 0.0535(8) Uani 1 1 d . . .
H6 H 1.144(6) 0.4017(6) 1.000(4) 0.063(8) Uiso 1 1 d . . .
C7 C 0.9454(7) 0.36950(6) 0.8245(3) 0.0484(7) Uani 1 1 d . . .
C8 C 0.9182(6) 0.35816(6) 0.6602(3) 0.0410(6) Uani 1 1 d . . .
H8 H 0.805(6) 0.3417(5) 0.624(3) 0.040(7) Uiso 1 1 d . . .
H17B H 1.333(7) 0.3168(6) 0.565(4) 0.067(9) Uiso 1 1 d . . .
H10 H 1.116(6) 0.3691(5) 0.322(3) 0.045(8) Uiso 1 1 d . . .
H12 H 0.563(5) 0.3590(5) 0.135(3) 0.044(7) Uiso 1 1 d . . .
H20 H 1.902(6) 0.5299(6) 0.204(3) 0.052(7) Uiso 1 1 d . . .
C9 C 1.0615(5) 0.37124(5) 0.5469(3) 0.0326(5) Uani 1 1 d . . .
N10 N 1.0436(5) 0.35913(4) 0.3864(3) 0.0362(5) Uani 1 1 d . . .
C11 C 0.8662(5) 0.33431(5) 0.3112(3) 0.0316(5) Uani 1 1 d . . .
C12 C 0.6127(6) 0.33916(5) 0.1724(3) 0.0378(6) Uani 1 1 d . . .
C13 C 0.4427(6) 0.31584(5) 0.0876(3) 0.0415(6) Uani 1 1 d . . .
C14 C 0.5231(6) 0.28734(5) 0.1426(3) 0.0386(6) Uani 1 1 d . . .
H14 H 0.407(5) 0.2712(5) 0.085(3) 0.040(7) Uiso 1 1 d . . .
C15 C 0.7735(5) 0.28279(5) 0.2816(3) 0.0330(5) Uani 1 1 d . . .
C16 C 0.9547(5) 0.30566(5) 0.3711(3) 0.0307(5) Uani 1 1 d . . .
C17 C 1.2273(6) 0.29974(6) 0.5191(4) 0.0410(6) Uani 1 1 d . . .
Cl18 Cl 0.86524(16) 0.246366(12) 0.34600(9) 0.0485(2) Uani 1 1 d . . .
C19 C 1.7442(7) 0.49618(6) 0.3130(4) 0.0557(8) Uani 1 1 d . . .
C20 C 1.8670(6) 0.50942(5) 0.1955(4) 0.0516(7) Uani 1 1 d . . .
C21 C 1.9346(5) 0.49321(5) 0.0653(4) 0.0420(6) Uani 1 1 d . . .
C22 C 1.8722(7) 0.46336(6) 0.0633(5) 0.0621(9) Uani 1 1 d . . .
C23 C 1.7528(7) 0.45150(6) 0.1866(5) 0.0608(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
O1 C3 1.329(3) . ?
O1 H1 0.92(3) . ?
O2 C3 1.221(3) . ?
N2 C23 1.329(4) . ?
N2 C19 1.334(3) . ?
C3 C4 1.473(3) . ?
C4 C5 1.401(3) . ?
C4 C9 1.415(3) . ?
C5 C6 1.363(4) . ?
C5 H5 0.92(2) . ?
C6 C7 1.378(4) . ?
C6 H6 0.95(3) . ?
C7 C8 1.369(3) . ?
C7 H7 0.94(3) . ?
C8 C9 1.401(3) . ?
C8 H8 0.91(2) . ?
C9 N10 1.364(3) . ?
N10 C11 1.422(3) . ?
N10 H10 0.83(2) . ?
C11 C12 1.385(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.95(2) . ?
C13 C14 1.378(3) . ?
C13 H13 0.98(2) . ?
C14 C15 1.375(3) . ?
C14 H14 0.95(2) . ?
C15 C16 1.396(3) . ?
C15 Cl18 1.741(2) . ?
C16 C17 1.490(3) . ?
C17 H17A 0.94(3) . ?
C17 H17C 0.96(3) . ?
C17 H17B 0.93(3) . ?
C19 C20 1.368(4) . ?
C19 H19 0.99(3) . ?
C20 C21 1.376(4) . ?
C20 H20 0.94(2) . ?
C21 C22 1.380(3) . ?
C21 C21 1.483(5) 3_965 ?
C22 C23 1.369(4) . ?
C22 H22 0.93(3) . ?
C23 H23 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109(2) . . ?
C23 N2 C19 116.2(3) . . ?
O2 C3 O1 121.1(2) . . ?
O2 C3 C4 124.3(2) . . ?
O1 C3 C4 114.6(2) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 120.4(2) . . ?
C9 C4 C3 121.07(19) . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 121.8(14) . . ?
C4 C5 H5 116.0(15) . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 119.5(17) . . ?
C7 C6 H6 121.5(17) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 120.9(16) . . ?
C6 C7 H7 118.3(16) . . ?
C7 C8 C9 121.4(3) . . ?
C7 C8 H8 119.5(15) . . ?
C9 C8 H8 119.1(15) . . ?
N10 C9 C8 121.1(2) . . ?
N10 C9 C4 121.0(2) . . ?
C8 C9 C4 117.9(2) . . ?
C9 N10 C11 125.22(19) . . ?
C9 N10 H10 115.5(17) . . ?
C11 N10 H10 118.1(17) . . ?
C12 C11 C16 121.2(2) . . ?
C12 C11 N10 118.2(2) . . ?
C16 C11 N10 120.5(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 121.1(15) . . ?
C11 C12 H12 118.1(15) . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.6(12) . . ?
C14 C13 H13 119.7(12) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.8(14) . . ?
C13 C14 H14 120.1(15) . . ?
C14 C15 C16 123.4(2) . . ?
C14 C15 Cl18 117.27(18) . . ?
C16 C15 Cl18 119.29(18) . . ?
C15 C16 C11 115.8(2) . . ?
C15 C16 C17 121.7(2) . . ?
C11 C16 C17 122.4(2) . . ?
C16 C17 H17A 111.1(18) . . ?
C16 C17 H17C 110.9(19) . . ?
H17A C17 H17C 106(2) . . ?
C16 C17 H17B 113.5(18) . . ?
H17A C17 H17B 109(2) . . ?
H17C C17 H17B 106(2) . . ?
N2 C19 C20 123.3(3) . . ?
N2 C19 H19 113.8(17) . . ?
C20 C19 H19 122.9(17) . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H20 118.7(15) . . ?
C21 C20 H20 120.5(15) . . ?
C20 C21 C22 115.8(2) . . ?
C20 C21 C21 122.4(3) . 3_965 ?
C22 C21 C21 121.8(3) . 3_965 ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 120.5(18) . . ?
C21 C22 H22 119.2(19) . . ?
N2 C23 C22 123.7(2) . . ?
N2 C23 H23 117.3(17) . . ?
C22 C23 H23 119.1(17) . . ?

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
O2 C3 C4 C5 177.1(2) . . . . ?
O1 C3 C4 C5 -4.5(3) . . . . ?
O2 C3 C4 C9 -3.7(4) . . . . ?
O1 C3 C4 C9 174.7(2) . . . . ?
C9 C4 C5 C6 -2.1(4) . . . . ?
C3 C4 C5 C6 177.1(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 2.5(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 N10 177.2(2) . . . . ?
C7 C8 C9 C4 -2.4(4) . . . . ?
C5 C4 C9 N10 -176.0(2) . . . . ?
C3 C4 C9 N10 4.9(3) . . . . ?
C5 C4 C9 C8 3.7(3) . . . . ?
C3 C4 C9 C8 -175.5(2) . . . . ?
C8 C9 N10 C11 5.2(4) . . . . ?
C4 C9 N10 C11 -175.1(2) . . . . ?
C9 N10 C11 C12 106.9(3) . . . . ?
C9 N10 C11 C16 -76.2(3) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?
N10 C11 C12 C13 176.0(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C13 C14 C15 Cl18 179.96(18) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
Cl18 C15 C16 C11 179.91(15) . . . . ?
C14 C15 C16 C17 -178.9(2) . . . . ?
Cl18 C15 C16 C17 0.8(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
N10 C11 C16 C15 -176.48(18) . . . . ?
C12 C11 C16 C17 179.5(2) . . . . ?
N10 C11 C16 C17 2.7(3) . . . . ?
C23 N2 C19 C20 -1.2(4) . . . . ?
N2 C19 C20 C21 1.3(5) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C19 C20 C21 C21 179.5(3) . . . 3_965 ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C21 C22 C23 179.6(3) 3_965 . . . ?
C19 N2 C23 C22 0.3(5) . . . . ?
C21 C22 C23 N2 0.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
