data_C21H16ClF2N3O4(18) 
_publ_contact_author_name        'Koya Prabhakara Rao'
_publ_contact_author_address     
;
New Generation Materials Lab (NGML), Department of Science and Humanities
Vignan's Foundation for Science Technology and Research (VFSTR) University
Vadlamudi, Guntur-522 213
Andhra Pradesh
India
;

_publ_contact_author_email       kprao2005@gmail.com

_publ_section_title              
;
Design and Synthesis of ‘Chloropicolinate Amides and Urea Derivatives’ as 
Novel Inhibitors for Mycobacterium Tuberculosis
;
_publ_author_name
;
'Koya Prabhakara Rao'
;
_publ_author_address     
;
New Generation Materials Lab (NGML), Department of Science and Humanities
Vignan's Foundation for Science Technology and Research (VFSTR) 
(Deemed to be University), Vadlamudi, Guntur-522 213
Andhra Pradesh
India
;

#==================================================================================

_publ_requested_journal		'ACS Omega'   
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum             'C21H16ClF2N3O4' 
_chemical_formula_weight          447.82 
 
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            monoclinic 
_symmetry_space_group_name_H-M    P21/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                    6.03(3) 
_cell_length_b                    30.28(16) 
_cell_length_c                    11.18(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.36(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      1979(17) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used      2650
_cell_measurement_theta_min        2.30
_cell_measurement_theta_max       18.84
 
_exptl_crystal_description       'NEEDLE'
_exptl_crystal_colour            'yellow'
_exptl_crystal_size_max           0.13 
_exptl_crystal_size_mid           0.06 
_exptl_crystal_size_min           0.04 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.503 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              920 
_exptl_absorpt_coefficient_mu     0.247 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9686 
_exptl_absorpt_correction_T_max   0.9902 
_exptl_absorpt_process_details    sadabs
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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       '\f and \w scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             29366 
_diffrn_reflns_av_R_equivalents   0.0779 
_diffrn_reflns_av_sigmaI/netI     0.0793 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -40 
_diffrn_reflns_limit_k_max        40 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.35 
_diffrn_reflns_theta_max          28.48 
_reflns_number_total              4961 
_reflns_number_gt                 2387 
_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, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3for Windows(Farrugia, 2012)' 
_computing_publication_material   wingx 
 
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1201P)^2^+0.2795P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4961 
_refine_ls_number_parameters      292 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1609 
_refine_ls_R_factor_gt            0.0739 
_refine_ls_wR_factor_ref          0.2447 
_refine_ls_wR_factor_gt           0.1969 
_refine_ls_goodness_of_fit_ref    1.027 
_refine_ls_restrained_S_all       1.027 
_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 
C1 C -0.0938(14) -0.0054(3) -0.3512(7) 0.134(3) Uani 1 1 d . . . 
H1A H -0.2358 -0.0197 -0.3894 0.201 Uiso 1 1 calc R . . 
H1B H -0.0805 -0.0024 -0.2643 0.201 Uiso 1 1 calc R . . 
H1C H 0.0312 -0.0229 -0.3642 0.201 Uiso 1 1 calc R . . 
C2 C 0.0970(8) 0.06177(15) -0.3642(4) 0.0616(11) Uani 1 1 d . . . 
C3 C 0.2968(9) 0.04852(14) -0.2828(4) 0.0680(13) Uani 1 1 d . . . 
H3 H 0.3140 0.0199 -0.2516 0.082 Uiso 1 1 calc R . . 
C4 C 0.4686(7) 0.07882(13) -0.2496(3) 0.0571(11) Uani 1 1 d . . . 
C5 C 0.4621(7) 0.12103(12) -0.2940(3) 0.0458(9) Uani 1 1 d . . . 
C6 C 0.2586(7) 0.13129(13) -0.3776(3) 0.0514(10) Uani 1 1 d . . . 
C7 C 0.0785(8) 0.10314(15) -0.4119(4) 0.0616(11) Uani 1 1 d . . . 
H7 H -0.0556 0.1121 -0.4674 0.074 Uiso 1 1 calc R . . 
C8 C 0.6514(7) 0.15395(11) -0.2611(3) 0.0449(9) Uani 1 1 d . . . 
C9 C 0.9607(6) 0.17955(11) -0.0866(3) 0.0412(8) Uani 1 1 d . . . 
C10 C 1.1047(7) 0.19582(13) -0.1544(3) 0.0495(9) Uani 1 1 d . . . 
H10 H 1.0707 0.1904 -0.2389 0.059 Uiso 1 1 calc R . . 
C11 C 1.2965(7) 0.21971(12) -0.1008(4) 0.0524(10) Uani 1 1 d . . . 
H11 H 1.3916 0.2300 -0.1486 0.063 Uiso 1 1 calc R . . 
C12 C 1.3479(7) 0.22833(12) 0.0225(4) 0.0542(10) Uani 1 1 d . . . 
H12 H 1.4760 0.2451 0.0591 0.065 Uiso 1 1 calc R . . 
C13 C 1.2091(6) 0.21207(12) 0.0919(4) 0.0484(9) Uani 1 1 d . . . 
H13 H 1.2474 0.2175 0.1764 0.058 Uiso 1 1 calc R . . 
C14 C 1.0139(6) 0.18788(10) 0.0415(3) 0.0398(8) Uani 1 1 d . . . 
C15 C 0.8723(6) 0.17192(10) 0.1236(3) 0.0391(8) Uani 1 1 d . . . 
C16 C 0.8715(6) 0.19423(12) 0.2303(3) 0.0441(8) Uani 1 1 d . . . 
H16 H 0.9578 0.2199 0.2496 0.053 Uiso 1 1 calc R . . 
C17 C 0.7445(6) 0.17923(11) 0.3097(3) 0.0421(8) Uani 1 1 d . . . 
C18 C 0.6168(6) 0.14119(12) 0.2735(3) 0.0471(9) Uani 1 1 d . . . 
C19 C 0.6230(6) 0.12092(11) 0.1651(3) 0.0450(9) Uani 1 1 d . . . 
C20 C 0.4924(8) 0.07990(13) 0.1242(4) 0.0570(11) Uani 1 1 d . . . 
C21 C 0.1474(10) 0.0495(2) 0.0198(7) 0.124(3) Uani 1 1 d . . . 
H21A H 0.0011 0.0598 -0.0270 0.187 Uiso 1 1 calc R . . 
H21B H 0.1281 0.0328 0.0895 0.187 Uiso 1 1 calc R . . 
H21C H 0.2150 0.0311 -0.0314 0.187 Uiso 1 1 calc R . . 
N1 N 0.7689(6) 0.15419(10) -0.1417(3) 0.0450(8) Uani 1 1 d . . . 
N2 N 0.7471(5) 0.13543(9) 0.0899(3) 0.0430(7) Uani 1 1 d . . . 
N3 N 0.7378(7) 0.20142(14) 0.4131(3) 0.0573(9) Uani 1 1 d . . . 
O1 O -0.0883(7) 0.03510(13) -0.4019(4) 0.0979(12) Uani 1 1 d . . . 
O2 O 0.6940(5) 0.17767(10) -0.3389(2) 0.0634(8) Uani 1 1 d . . . 
O3 O 0.5714(9) 0.04456(13) 0.1431(5) 0.168(3) Uani 1 1 d . . . 
O4 O 0.2930(6) 0.08631(11) 0.0617(4) 0.1067(14) Uani 1 1 d . . . 
F1 F 0.2304(4) 0.17180(8) -0.4256(2) 0.0687(7) Uani 1 1 d . . . 
F2 F 0.6631(5) 0.06519(8) -0.1691(3) 0.0895(10) Uani 1 1 d . . . 
Cl Cl 0.4483(2) 0.12078(4) 0.36354(10) 0.0780(4) Uani 1 1 d . . . 
H1 H 0.678(6) 0.1849(11) 0.467(3) 0.042(10) Uiso 1 1 d . . . 
H2 H 0.845(8) 0.2209(14) 0.440(4) 0.064(14) Uiso 1 1 d . . . 
H4 H 0.707(6) 0.1402(12) -0.095(3) 0.038(10) Uiso 1 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C1 0.162(7) 0.127(6) 0.119(6) -0.024(5) 0.046(5) -0.050(5) 
C2 0.068(3) 0.064(3) 0.052(2) -0.010(2) 0.013(2) -0.014(2) 
C3 0.099(4) 0.045(2) 0.053(3) -0.0004(19) 0.006(3) -0.008(2) 
C4 0.068(3) 0.051(2) 0.043(2) 0.0020(18) -0.003(2) 0.004(2) 
C5 0.058(2) 0.047(2) 0.0320(18) -0.0035(15) 0.0100(17) 0.0045(18) 
C6 0.063(3) 0.050(2) 0.041(2) -0.0005(17) 0.012(2) 0.008(2) 
C7 0.061(3) 0.069(3) 0.050(2) 0.001(2) 0.005(2) 0.007(2) 
C8 0.057(2) 0.045(2) 0.0325(19) 0.0017(15) 0.0111(17) 0.0046(17) 
C9 0.051(2) 0.0339(18) 0.0393(19) 0.0026(14) 0.0118(17) 0.0029(16) 
C10 0.055(2) 0.055(2) 0.041(2) 0.0040(17) 0.0170(18) 0.0097(19) 
C11 0.055(3) 0.052(2) 0.055(2) 0.0116(18) 0.023(2) 0.0050(19) 
C12 0.046(2) 0.048(2) 0.068(3) 0.0053(19) 0.012(2) -0.0034(18) 
C13 0.053(2) 0.046(2) 0.043(2) -0.0040(16) 0.0083(18) -0.0026(18) 
C14 0.047(2) 0.0348(18) 0.0380(19) 0.0005(14) 0.0114(16) 0.0022(15) 
C15 0.047(2) 0.0357(18) 0.0319(18) 0.0019(14) 0.0042(15) 0.0045(16) 
C16 0.052(2) 0.0400(19) 0.0382(19) -0.0027(15) 0.0076(17) -0.0039(16) 
C17 0.044(2) 0.046(2) 0.0349(18) 0.0031(15) 0.0065(16) 0.0074(16) 
C18 0.049(2) 0.055(2) 0.037(2) 0.0056(16) 0.0090(17) -0.0009(18) 
C19 0.052(2) 0.0399(19) 0.040(2) 0.0046(15) 0.0071(17) -0.0021(16) 
C20 0.070(3) 0.044(2) 0.055(3) 0.0052(18) 0.014(2) -0.009(2) 
C21 0.078(4) 0.108(5) 0.175(7) -0.049(5) 0.009(4) -0.040(4) 
N1 0.061(2) 0.0455(18) 0.0302(16) -0.0013(13) 0.0137(15) -0.0062(15) 
N2 0.0555(19) 0.0373(15) 0.0350(16) -0.0003(12) 0.0090(14) -0.0023(14) 
N3 0.069(3) 0.067(2) 0.0385(19) -0.0047(17) 0.0173(18) -0.002(2) 
O1 0.123(3) 0.077(2) 0.096(3) -0.010(2) 0.030(2) -0.036(2) 
O2 0.075(2) 0.0769(19) 0.0370(14) 0.0137(13) 0.0106(14) -0.0056(15) 
O3 0.156(4) 0.048(2) 0.238(6) 0.028(3) -0.069(4) -0.023(2) 
O4 0.065(2) 0.065(2) 0.160(4) -0.026(2) -0.028(2) -0.0053(17) 
F1 0.0739(17) 0.0597(15) 0.0663(16) 0.0149(11) 0.0056(13) 0.0114(12) 
F2 0.103(2) 0.0564(15) 0.0827(19) 0.0124(13) -0.0276(17) -0.0004(14) 
Cl 0.0866(9) 0.0984(9) 0.0571(7) 0.0019(6) 0.0331(6) -0.0257(7) 
 
_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 
C1 O1 1.355(10) . ? 
C1 H1A 0.9600 . ? 
C1 H1B 0.9600 . ? 
C1 H1C 0.9600 . ? 
C2 C7 1.355(8) . ? 
C2 O1 1.358(7) . ? 
C2 C3 1.378(8) . ? 
C3 C4 1.365(8) . ? 
C3 H3 0.9300 . ? 
C4 F2 1.354(6) . ? 
C4 C5 1.368(8) . ? 
C5 C6 1.381(7) . ? 
C5 C8 1.491(7) . ? 
C6 F1 1.333(7) . ? 
C6 C7 1.359(7) . ? 
C7 H7 0.9300 . ? 
C8 O2 1.204(6) . ? 
C8 N1 1.348(7) . ? 
C9 C10 1.377(6) . ? 
C9 N1 1.398(7) . ? 
C9 C14 1.411(8) . ? 
C10 C11 1.370(7) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.361(9) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.367(7) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.382(7) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.482(7) . ? 
C15 N2 1.338(7) . ? 
C15 C16 1.372(7) . ? 
C16 C17 1.385(6) . ? 
C16 H16 0.9300 . ? 
C17 N3 1.347(7) . ? 
C17 C18 1.389(7) . ? 
C18 C19 1.368(7) . ? 
C18 Cl 1.714(6) . ? 
C19 N2 1.331(6) . ? 
C19 C20 1.481(8) . ? 
C20 O3 1.169(7) . ? 
C20 O4 1.248(7) . ? 
C21 O4 1.424(8) . ? 
C21 H21A 0.9600 . ? 
C21 H21B 0.9600 . ? 
C21 H21C 0.9600 . ? 
N1 H4 0.83(3) . ? 
N3 H1 0.92(4) . ? 
N3 H2 0.87(4) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
O1 C1 H1A 109.5 . . ? 
O1 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
O1 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C7 C2 O1 116.5(5) . . ? 
C7 C2 C3 120.2(4) . . ? 
O1 C2 C3 123.3(5) . . ? 
C4 C3 C2 117.7(5) . . ? 
C4 C3 H3 121.1 . . ? 
C2 C3 H3 121.1 . . ? 
F2 C4 C3 116.8(5) . . ? 
F2 C4 C5 117.9(4) . . ? 
C3 C4 C5 125.3(4) . . ? 
C4 C5 C6 113.4(4) . . ? 
C4 C5 C8 125.7(4) . . ? 
C6 C5 C8 121.0(4) . . ? 
F1 C6 C7 116.8(4) . . ? 
F1 C6 C5 118.9(4) . . ? 
C7 C6 C5 124.3(5) . . ? 
C2 C7 C6 119.1(5) . . ? 
C2 C7 H7 120.4 . . ? 
C6 C7 H7 120.4 . . ? 
O2 C8 N1 124.0(4) . . ? 
O2 C8 C5 120.5(4) . . ? 
N1 C8 C5 115.5(3) . . ? 
C10 C9 N1 121.4(4) . . ? 
C10 C9 C14 118.6(4) . . ? 
N1 C9 C14 120.0(3) . . ? 
C11 C10 C9 121.8(5) . . ? 
C11 C10 H10 119.1 . . ? 
C9 C10 H10 119.1 . . ? 
C12 C11 C10 120.0(4) . . ? 
C12 C11 H11 120.0 . . ? 
C10 C11 H11 120.0 . . ? 
C11 C12 C13 119.2(4) . . ? 
C11 C12 H12 120.4 . . ? 
C13 C12 H12 120.4 . . ? 
C12 C13 C14 122.6(5) . . ? 
C12 C13 H13 118.7 . . ? 
C14 C13 H13 118.7 . . ? 
C13 C14 C9 117.7(3) . . ? 
C13 C14 C15 118.9(4) . . ? 
C9 C14 C15 123.4(4) . . ? 
N2 C15 C16 121.8(3) . . ? 
N2 C15 C14 117.8(4) . . ? 
C16 C15 C14 120.3(4) . . ? 
C15 C16 C17 121.2(4) . . ? 
C15 C16 H16 119.4 . . ? 
C17 C16 H16 119.4 . . ? 
N3 C17 C16 121.7(5) . . ? 
N3 C17 C18 122.1(4) . . ? 
C16 C17 C18 116.1(4) . . ? 
C19 C18 C17 119.7(4) . . ? 
C19 C18 Cl 120.6(4) . . ? 
C17 C18 Cl 119.7(4) . . ? 
N2 C19 C18 123.7(4) . . ? 
N2 C19 C20 114.9(4) . . ? 
C18 C19 C20 121.4(4) . . ? 
O3 C20 O4 122.5(4) . . ? 
O3 C20 C19 123.4(6) . . ? 
O4 C20 C19 114.0(4) . . ? 
O4 C21 H21A 109.5 . . ? 
O4 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
O4 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
C8 N1 C9 127.9(3) . . ? 
C8 N1 H4 114(2) . . ? 
C9 N1 H4 117(2) . . ? 
C19 N2 C15 117.5(4) . . ? 
C17 N3 H1 113(2) . . ? 
C17 N3 H2 117(3) . . ? 
H1 N3 H2 121(4) . . ? 
C1 O1 C2 120.8(5) . . ? 
C20 O4 C21 119.5(5) . . ? 
 
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 
C7 C2 C3 C4 2.3(6) . . . . ? 
O1 C2 C3 C4 -178.3(4) . . . . ? 
C2 C3 C4 F2 179.7(4) . . . . ? 
C2 C3 C4 C5 -2.5(7) . . . . ? 
F2 C4 C5 C6 178.5(3) . . . . ? 
C3 C4 C5 C6 0.8(6) . . . . ? 
F2 C4 C5 C8 -0.3(6) . . . . ? 
C3 C4 C5 C8 -178.1(4) . . . . ? 
C4 C5 C6 F1 178.8(3) . . . . ? 
C8 C5 C6 F1 -2.3(5) . . . . ? 
C4 C5 C6 C7 1.2(6) . . . . ? 
C8 C5 C6 C7 -179.9(4) . . . . ? 
O1 C2 C7 C6 -180.0(4) . . . . ? 
C3 C2 C7 C6 -0.6(6) . . . . ? 
F1 C6 C7 C2 -179.0(4) . . . . ? 
C5 C6 C7 C2 -1.3(6) . . . . ? 
C4 C5 C8 O2 139.4(4) . . . . ? 
C6 C5 C8 O2 -39.4(5) . . . . ? 
C4 C5 C8 N1 -39.4(5) . . . . ? 
C6 C5 C8 N1 141.8(4) . . . . ? 
N1 C9 C10 C11 -178.2(3) . . . . ? 
C14 C9 C10 C11 0.0(5) . . . . ? 
C9 C10 C11 C12 -0.7(6) . . . . ? 
C10 C11 C12 C13 1.5(6) . . . . ? 
C11 C12 C13 C14 -1.5(6) . . . . ? 
C12 C13 C14 C9 0.8(5) . . . . ? 
C12 C13 C14 C15 -179.4(3) . . . . ? 
C10 C9 C14 C13 0.0(5) . . . . ? 
N1 C9 C14 C13 178.2(3) . . . . ? 
C10 C9 C14 C15 -179.8(3) . . . . ? 
N1 C9 C14 C15 -1.6(5) . . . . ? 
C13 C14 C15 N2 -153.1(3) . . . . ? 
C9 C14 C15 N2 26.7(5) . . . . ? 
C13 C14 C15 C16 26.9(5) . . . . ? 
C9 C14 C15 C16 -153.3(3) . . . . ? 
N2 C15 C16 C17 1.6(5) . . . . ? 
C14 C15 C16 C17 -178.4(3) . . . . ? 
C15 C16 C17 N3 -178.3(3) . . . . ? 
C15 C16 C17 C18 -1.1(5) . . . . ? 
N3 C17 C18 C19 177.4(4) . . . . ? 
C16 C17 C18 C19 0.2(5) . . . . ? 
N3 C17 C18 Cl -1.2(5) . . . . ? 
C16 C17 C18 Cl -178.3(3) . . . . ? 
C17 C18 C19 N2 0.3(6) . . . . ? 
Cl C18 C19 N2 178.9(3) . . . . ? 
C17 C18 C19 C20 179.0(4) . . . . ? 
Cl C18 C19 C20 -2.4(5) . . . . ? 
N2 C19 C20 O3 83.7(7) . . . . ? 
C18 C19 C20 O3 -95.1(7) . . . . ? 
N2 C19 C20 O4 -92.6(5) . . . . ? 
C18 C19 C20 O4 88.6(6) . . . . ? 
O2 C8 N1 C9 -2.6(6) . . . . ? 
C5 C8 N1 C9 176.2(3) . . . . ? 
C10 C9 N1 C8 -24.4(6) . . . . ? 
C14 C9 N1 C8 157.5(4) . . . . ? 
C18 C19 N2 C15 0.1(5) . . . . ? 
C20 C19 N2 C15 -178.7(3) . . . . ? 
C16 C15 N2 C19 -1.0(5) . . . . ? 
C14 C15 N2 C19 179.0(3) . . . . ? 
C7 C2 O1 C1 -174.2(5) . . . . ? 
C3 C2 O1 C1 6.4(7) . . . . ? 
O3 C20 O4 C21 5.5(9) . . . . ? 
C19 C20 O4 C21 -178.2(5) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.993 
_diffrn_reflns_theta_full              28.48 
_diffrn_measured_fraction_theta_full   0.993 
_refine_diff_density_max    0.712 
_refine_diff_density_min   -0.391 
_refine_diff_density_rms    0.065