# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_872
_database_code_depnum_ccdc_archive 'CCDC 1569338'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"Ethyl 3'-(4- methoxyphenyl)-1',2-dimethyl-1'H,2H-3,4'-bipyrazole-5-carboxylate"
_chemical_name_common            ?
_chemical_melting_point          '411--412 '
_chemical_formula_moiety         C18H20N4O3
_chemical_formula_sum            'C18 H20 N4 O3'
_chemical_formula_weight         340.38

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.7419(6)
_cell_length_b                   10.7719(7)
_cell_length_c                   10.9487(7)
_cell_angle_alpha                65.802(7)
_cell_angle_beta                 70.156(6)
_cell_angle_gamma                75.680(6)
_cell_volume                     877.51(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8223
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         30.68
_reflns_number_total             4776
_reflns_number_gt                3174
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1070P)²+0.0600P] where P=(Fo²+2Fc²)/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         4776
_refine_ls_number_parameters     255
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1901
_refine_ls_wR_factor_gt          0.1565
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.011
_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 0.8010(2) 0.48390(17) 0.98557(17) 0.0625(4) Uani 0.87 1 d P A 1
O2 O 0.8030(5) 0.2949(3) 0.9382(4) 0.0819(9) Uani 0.87 1 d P A 1
O3 O 0.38832(18) 1.15291(17) 0.86783(16) 0.0776(5) Uani 1 1 d . . .
N1 N 0.97830(18) 0.97176(15) 0.24966(14) 0.0516(4) Uani 1 1 d . . .
N2 N 0.88980(17) 1.04892(14) 0.32751(14) 0.0488(3) Uani 1 1 d . . .
N3 N 0.79082(17) 0.58488(14) 0.55242(15) 0.0493(3) Uani 1 1 d . . .
N4 N 0.77685(19) 0.47472(14) 0.67083(16) 0.0550(4) Uani 1 1 d . . .
C3 C 0.81544(18) 0.96039(15) 0.44845(16) 0.0421(3) Uani 1 1 d . . .
C4 C 0.85835(19) 0.82454(15) 0.44816(16) 0.0434(4) Uani 1 1 d . . .
C5 C 0.9633(2) 0.83830(17) 0.31831(18) 0.0503(4) Uani 1 1 d . . .
H5 H 1.0144 0.7677 0.2845 0.060 Uiso 1 1 calc R . .
C8 C 0.8010(2) 0.51805(16) 0.76038(18) 0.0519(4) Uani 1 1 d . A .
C9 C 0.8292(2) 0.65493(16) 0.69987(17) 0.0506(4) Uani 1 1 d . . .
H9 H 0.8476 0.7073 0.7420 0.061 Uiso 1 1 calc R . .
C10 C 0.82392(19) 0.69606(15) 0.56432(17) 0.0442(4) Uani 1 1 d . . .
C11 C 1.0891(3) 1.0344(2) 0.1146(2) 0.0722(6) Uani 1 1 d . . .
H11A H 1.0298 1.1112 0.0583 0.108 Uiso 1 1 calc R . .
H11B H 1.1354 0.9682 0.0698 0.108 Uiso 1 1 calc R . .
H11C H 1.1754 1.0650 0.1267 0.108 Uiso 1 1 calc R . .
C12 C 0.7630(3) 0.5754(2) 0.4330(2) 0.0685(5) Uani 1 1 d . . .
H12A H 0.8624 0.5360 0.3828 0.103 Uiso 1 1 calc R . .
H12B H 0.7301 0.6654 0.3732 0.103 Uiso 1 1 calc R . .
H12C H 0.6783 0.5185 0.4643 0.103 Uiso 1 1 calc R . .
C15 C 0.8003(3) 0.41958(19) 0.9018(2) 0.0628(5) Uani 1 1 d . . .
C16 C 0.8086(4) 0.3987(3) 1.1283(3) 0.0744(7) Uani 0.87 1 d P A 1
H16A H 0.8814 0.3145 1.1289 0.089 Uiso 0.87 1 calc PR A 1
H16B H 0.8522 0.4474 1.1641 0.089 Uiso 0.87 1 calc PR A 1
C17 C 0.6446(4) 0.3663(3) 1.2172(4) 0.0965(10) Uani 0.87 1 d P A 1
H17A H 0.5721 0.4499 1.2143 0.145 Uiso 0.87 1 calc PR A 1
H17B H 0.6500 0.3138 1.3111 0.145 Uiso 0.87 1 calc PR A 1
H17C H 0.6043 0.3139 1.1845 0.145 Uiso 0.87 1 calc PR A 1
C18 C 0.70558(18) 1.01090(15) 0.55842(16) 0.0412(3) Uani 1 1 d . . .
C19 C 0.5633(2) 0.95277(17) 0.64622(18) 0.0484(4) Uani 1 1 d . . .
H19 H 0.5374 0.8795 0.6360 0.058 Uiso 1 1 calc R . .
C20 C 0.4610(2) 1.00191(19) 0.74749(19) 0.0538(4) Uani 1 1 d . . .
H20 H 0.3669 0.9615 0.8054 0.065 Uiso 1 1 calc R . .
C21 C 0.4971(2) 1.11122(18) 0.76388(18) 0.0512(4) Uani 1 1 d . . .
C22 C 0.6356(2) 1.17229(18) 0.67688(19) 0.0528(4) Uani 1 1 d . . .
H22 H 0.6601 1.2465 0.6865 0.063 Uiso 1 1 calc R . .
C23 C 0.7380(2) 1.12172(17) 0.57483(17) 0.0481(4) Uani 1 1 d . . .
H23 H 0.8309 1.1634 0.5158 0.058 Uiso 1 1 calc R . .
C24 C 0.4384(4) 1.2380(3) 0.9109(3) 0.1039(10) Uani 1 1 d . . .
H24A H 0.4579 1.3239 0.8356 0.156 Uiso 1 1 calc R . .
H24B H 0.5375 1.1946 0.9385 0.156 Uiso 1 1 calc R . .
H24C H 0.3543 1.2540 0.9882 0.156 Uiso 1 1 calc R . .
O1A O 0.7081(14) 0.4670(10) 0.9927(10) 0.049(2) Uani 0.13 1 d P A 2
C17A C 0.750(3) 0.431(2) 1.217(2) 0.0965(10) Uani 0.13 1 d P A 2
H17D H 0.7923 0.5164 1.1591 0.145 Uiso 0.13 1 calc PR A 2
H17E H 0.8319 0.3656 1.2574 0.145 Uiso 0.13 1 calc PR A 2
H17F H 0.6551 0.4444 1.2888 0.145 Uiso 0.13 1 calc PR A 2
C16A C 0.703(2) 0.3783(18) 1.1314(15) 0.061(4) Uani 0.13 1 d PU A 2
H16C H 0.7745 0.2942 1.1289 0.073 Uiso 0.13 1 calc PR A 2
H16D H 0.5922 0.3545 1.1778 0.073 Uiso 0.13 1 calc PR A 2
O2A O 0.847(4) 0.315(3) 0.920(3) 0.0819(9) Uani 0.13 1 d P A 2


_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 C15 1.359(3) . ?
O1 C16 1.468(3) . ?
O2 C15 1.231(4) . ?
O3 C21 1.369(2) . ?
O3 C24 1.395(3) . ?
N1 C5 1.338(2) . ?
N1 N2 1.3531(19) . ?
N1 C11 1.453(2) . ?
N2 C3 1.331(2) . ?
N3 N4 1.3442(19) . ?
N3 C10 1.364(2) . ?
N3 C12 1.455(2) . ?
N4 C8 1.337(2) . ?
C3 C4 1.419(2) . ?
C3 C18 1.470(2) . ?
C4 C5 1.376(2) . ?
C4 C10 1.458(2) . ?
C5 H5 0.9300 . ?
C8 C9 1.393(2) . ?
C8 C15 1.474(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 O2A 1.06(3) . ?
C15 O1A 1.253(11) . ?
C16 C17 1.465(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.384(2) . ?
C18 C19 1.394(2) . ?
C19 C20 1.372(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O1A C16A 1.417(18) . ?
C17A C16A 1.47(3) . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?

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
C15 O1 C16 117.84(18) . . ?
C21 O3 C24 117.97(17) . . ?
C5 N1 N2 112.28(14) . . ?
C5 N1 C11 127.45(16) . . ?
N2 N1 C11 119.83(15) . . ?
C3 N2 N1 105.12(13) . . ?
N4 N3 C10 112.92(13) . . ?
N4 N3 C12 118.75(14) . . ?
C10 N3 C12 128.27(15) . . ?
C8 N4 N3 104.13(14) . . ?
N2 C3 C4 110.79(14) . . ?
N2 C3 C18 119.58(13) . . ?
C4 C3 C18 129.63(14) . . ?
C5 C4 C3 104.35(14) . . ?
C5 C4 C10 126.35(14) . . ?
C3 C4 C10 128.56(15) . . ?
N1 C5 C4 107.46(15) . . ?
N1 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
N4 C8 C9 111.94(15) . . ?
N4 C8 C15 118.63(16) . . ?
C9 C8 C15 129.39(17) . . ?
C10 C9 C8 105.23(15) . . ?
C10 C9 H9 127.4 . . ?
C8 C9 H9 127.4 . . ?
N3 C10 C9 105.77(14) . . ?
N3 C10 C4 123.76(14) . . ?
C9 C10 C4 130.30(15) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2A C15 O2 19.9(18) . . ?
O2A C15 O1A 125.4(18) . . ?
O2 C15 O1A 113.0(5) . . ?
O2A C15 O1 123(2) . . ?
O2 C15 O1 124.4(3) . . ?
O1A C15 O1 37.6(4) . . ?
O2A C15 C8 121.0(19) . . ?
O2 C15 C8 124.3(3) . . ?
O1A C15 C8 111.6(5) . . ?
O1 C15 C8 111.20(16) . . ?
C17 C16 O1 110.0(3) . . ?
C17 C16 H16A 109.7 . . ?
O1 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
O1 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C23 C18 C19 117.72(15) . . ?
C23 C18 C3 120.57(14) . . ?
C19 C18 C3 121.68(14) . . ?
C20 C19 C18 121.06(15) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.33(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O3 C21 C22 123.90(16) . . ?
O3 C21 C20 116.24(16) . . ?
C22 C21 C20 119.86(15) . . ?
C21 C22 C23 119.23(16) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C18 C23 C22 121.78(16) . . ?
C18 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 O1A C16A 114.7(11) . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
O1A C16A C17A 116.7(14) . . ?
O1A C16A H16C 108.1 . . ?
C17A C16A H16C 108.1 . . ?
O1A C16A H16D 108.1 . . ?
C17A C16A H16D 108.1 . . ?
H16C C16A H16D 107.3 . . ?

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
C5 N1 N2 C3 -0.76(18) . . . . ?
C11 N1 N2 C3 -173.72(16) . . . . ?
C10 N3 N4 C8 0.35(19) . . . . ?
C12 N3 N4 C8 -177.00(16) . . . . ?
N1 N2 C3 C4 0.54(18) . . . . ?
N1 N2 C3 C18 -179.05(13) . . . . ?
N2 C3 C4 C5 -0.14(19) . . . . ?
C18 C3 C4 C5 179.39(15) . . . . ?
N2 C3 C4 C10 170.37(15) . . . . ?
C18 C3 C4 C10 -10.1(3) . . . . ?
N2 N1 C5 C4 0.7(2) . . . . ?
C11 N1 C5 C4 172.98(18) . . . . ?
C3 C4 C5 N1 -0.32(18) . . . . ?
C10 C4 C5 N1 -171.11(15) . . . . ?
N3 N4 C8 C9 0.34(19) . . . . ?
N3 N4 C8 C15 -177.69(15) . . . . ?
N4 C8 C9 C10 -0.9(2) . . . . ?
C15 C8 C9 C10 176.89(18) . . . . ?
N4 N3 C10 C9 -0.89(19) . . . . ?
C12 N3 C10 C9 176.15(18) . . . . ?
N4 N3 C10 C4 174.67(14) . . . . ?
C12 N3 C10 C4 -8.3(3) . . . . ?
C8 C9 C10 N3 1.01(18) . . . . ?
C8 C9 C10 C4 -174.14(16) . . . . ?
C5 C4 C10 N3 -46.4(2) . . . . ?
C3 C4 C10 N3 145.05(17) . . . . ?
C5 C4 C10 C9 128.0(2) . . . . ?
C3 C4 C10 C9 -40.6(3) . . . . ?
C16 O1 C15 O2A -22.6(19) . . . . ?
C16 O1 C15 O2 1.2(4) . . . . ?
C16 O1 C15 O1A 84.7(8) . . . . ?
C16 O1 C15 C8 -177.02(19) . . . . ?
N4 C8 C15 O2A 35(2) . . . . ?
C9 C8 C15 O2A -143(2) . . . . ?
N4 C8 C15 O2 11.2(4) . . . . ?
C9 C8 C15 O2 -166.5(3) . . . . ?
N4 C8 C15 O1A -130.1(5) . . . . ?
C9 C8 C15 O1A 52.3(6) . . . . ?
N4 C8 C15 O1 -170.57(17) . . . . ?
C9 C8 C15 O1 11.8(3) . . . . ?
C15 O1 C16 C17 -82.3(3) . . . . ?
N2 C3 C18 C23 -34.2(2) . . . . ?
C4 C3 C18 C23 146.25(17) . . . . ?
N2 C3 C18 C19 143.55(16) . . . . ?
C4 C3 C18 C19 -36.0(2) . . . . ?
C23 C18 C19 C20 -1.4(2) . . . . ?
C3 C18 C19 C20 -179.30(15) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C24 O3 C21 C22 -16.2(3) . . . . ?
C24 O3 C21 C20 164.4(2) . . . . ?
C19 C20 C21 O3 -179.78(16) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
O3 C21 C22 C23 179.91(17) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C19 C18 C23 C22 1.5(2) . . . . ?
C3 C18 C23 C22 179.41(15) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?
O2A C15 O1A C16A 17(3) . . . . ?
O2 C15 O1A C16A 34.9(12) . . . . ?
O1 C15 O1A C16A -82.2(11) . . . . ?
C8 C15 O1A C16A -179.3(9) . . . . ?
C15 O1A C16A C17A 121.8(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOH-H2O'
####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1569341'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 N4 O2'
_chemical_formula_weight         434.49

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   8.521(5)
_cell_length_b                   10.998(5)
_cell_length_c                   23.489(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.24(4)
_cell_angle_gamma                90.00
_cell_volume                     2197.8(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8310
_cell_measurement_theta_min      3.7538
_cell_measurement_theta_max      65.2072

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_min  0.82866
_exptl_absorpt_correction_T_max  1.21647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18375
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3813
_reflns_number_gt                2943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0985P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3813
_refine_ls_number_parameters     614
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
N1A N 0.6570(6) 0.9545(4) 0.2068(2) 0.0436(11) Uani 1 1 d . A .
O1A O 0.9063(9) 0.6620(6) 0.3019(3) 0.099(2) Uani 1 1 d . . .
N2A N 0.6991(6) 0.8402(5) 0.1992(2) 0.0500(13) Uani 1 1 d . A .
O2A O 0.8196(5) 0.6135(4) 0.2162(2) 0.0624(11) Uani 1 1 d . . .
N3A N 0.5542(6) 1.2875(5) 0.3054(2) 0.0479(13) Uani 1 1 d . A .
C3A C 0.7637(7) 0.8042(5) 0.2484(3) 0.0466(15) Uani 1 1 d . . .
N4A N 0.7050(6) 1.2942(5) 0.3256(2) 0.0585(15) Uani 1 1 d . A .
C4A C 0.7620(7) 0.8990(6) 0.2891(3) 0.0509(15) Uani 1 1 d . A .
H4AA H 0.8007 0.8964 0.3269 0.061 Uiso 1 1 calc R . .
C5A C 0.6915(6) 0.9951(6) 0.2610(2) 0.0433(14) Uani 1 1 d . . .
C6A C 0.8341(9) 0.6831(6) 0.2588(3) 0.0638(19) Uani 1 1 d . A .
C7B C 0.7881(19) 0.4657(13) 0.2204(7) 0.055(3) Uani 0.25 1 d PU A 1
H7BA H 0.7851 0.4362 0.2593 0.066 Uiso 0.25 1 calc PR A 1
H7BB H 0.6965 0.4384 0.1975 0.066 Uiso 0.25 1 calc PR A 1
C7A C 0.8948(10) 0.4987(7) 0.2240(4) 0.0501(18) Uani 0.75 1 d PU A 2
H7AA H 0.8786 0.4674 0.2618 0.060 Uiso 0.75 1 calc PR A 2
H7AB H 1.0069 0.5066 0.2197 0.060 Uiso 0.75 1 calc PR A 2
C8B C 0.936(2) 0.4408(18) 0.1946(7) 0.065(4) Uani 0.25 1 d PU A 1
H8BA H 0.9502 0.3545 0.1915 0.098 Uiso 0.25 1 calc PR A 1
H8BB H 1.0212 0.4748 0.2179 0.098 Uiso 0.25 1 calc PR A 1
H8BC H 0.9342 0.4768 0.1573 0.098 Uiso 0.25 1 calc PR A 1
C8A C 0.8248(12) 0.4160(8) 0.1803(5) 0.071(2) Uani 0.75 1 d PU A 2
H8AA H 0.8729 0.3373 0.1844 0.107 Uiso 0.75 1 calc PR A 2
H8AB H 0.8420 0.4478 0.1431 0.107 Uiso 0.75 1 calc PR A 2
H8AC H 0.7140 0.4090 0.1849 0.107 Uiso 0.75 1 calc PR A 2
C9A C 0.5918(7) 1.0235(6) 0.1598(3) 0.0463(15) Uani 1 1 d . . .
C10A C 0.4645(8) 0.9777(7) 0.1287(3) 0.0578(17) Uani 1 1 d . A .
H10A H 0.4221 0.9033 0.1388 0.069 Uiso 1 1 calc R . .
C11B C 0.4007(10) 1.0385(8) 0.0843(3) 0.078(2) Uani 1 1 d . . .
H11A H 0.3141 1.0075 0.0632 0.094 Uiso 1 1 calc R A .
C12A C 0.4696(12) 1.1552(7) 0.0693(3) 0.077(2) Uani 1 1 d . A .
H12A H 0.4297 1.1984 0.0377 0.092 Uiso 1 1 calc R . .
C13A C 0.5914(11) 1.1990(7) 0.1018(4) 0.072(2) Uani 1 1 d . . .
H13A H 0.6331 1.2749 0.0939 0.086 Uiso 1 1 calc R A .
C14A C 0.6547(9) 1.1311(7) 0.1471(3) 0.0573(17) Uani 1 1 d . A .
H14A H 0.7413 1.1603 0.1688 0.069 Uiso 1 1 calc R . .
C15A C 0.7663(8) 1.1903(6) 0.3114(3) 0.0577(17) Uani 1 1 d . . .
H15A H 0.8706 1.1696 0.3201 0.069 Uiso 1 1 calc R A .
C16A C 0.6606(7) 1.1141(6) 0.2820(3) 0.0479(15) Uani 1 1 d . A .
C17A C 0.5208(7) 1.1797(5) 0.2789(3) 0.0423(13) Uani 1 1 d . . .
C18A C 0.3700(7) 1.1406(6) 0.2535(3) 0.0445(14) Uani 1 1 d . A .
C19A C 0.3039(8) 1.0367(7) 0.2728(3) 0.0566(17) Uani 1 1 d . . .
H19A H 0.3555 0.9937 0.3024 0.068 Uiso 1 1 calc R A .
C20A C 0.1619(9) 0.9936(9) 0.2495(4) 0.076(2) Uani 1 1 d . A .
H20B H 0.1176 0.9229 0.2633 0.091 Uiso 1 1 calc R . .
C21A C 0.0891(8) 1.0567(10) 0.2062(4) 0.086(3) Uani 1 1 d . . .
H21A H -0.0064 1.0291 0.1899 0.103 Uiso 1 1 calc R A .
C22A C 0.1551(10) 1.1611(9) 0.1862(4) 0.073(2) Uani 1 1 d . A .
H22A H 0.1042 1.2025 0.1559 0.088 Uiso 1 1 calc R . .
C23A C 0.2936(8) 1.2054(7) 0.2097(3) 0.0540(17) Uani 1 1 d . . .
H23A H 0.3358 1.2775 0.1966 0.065 Uiso 1 1 calc R A .
C24A C 0.4566(8) 1.3899(6) 0.3137(3) 0.0512(16) Uani 1 1 d . . .
C25A C 0.3004(8) 1.3759(7) 0.3221(3) 0.0588(18) Uani 1 1 d . A .
H25A H 0.2562 1.2987 0.3232 0.071 Uiso 1 1 calc R . .
C26A C 0.2084(10) 1.4785(8) 0.3289(3) 0.068(2) Uani 1 1 d . . .
H26A H 0.1014 1.4704 0.3339 0.082 Uiso 1 1 calc R A .
C27A C 0.2759(11) 1.5920(7) 0.3283(3) 0.075(2) Uani 1 1 d . A .
H27A H 0.2136 1.6607 0.3318 0.090 Uiso 1 1 calc R . .
C28A C 0.4294(12) 1.6045(7) 0.3226(4) 0.078(2) Uani 1 1 d . . .
H28B H 0.4745 1.6815 0.3233 0.093 Uiso 1 1 calc R A .
C29A C 0.5226(10) 1.5022(7) 0.3157(3) 0.064(2) Uani 1 1 d . A .
H29A H 0.6302 1.5108 0.3124 0.077 Uiso 1 1 calc R . .
N1 N 0.0973(6) 0.4556(4) 0.0370(2) 0.0470(12) Uani 1 1 d . . .
O1 O -0.1451(9) 0.1569(5) -0.0592(2) 0.0910(19) Uani 1 1 d . . .
N2 N 0.0533(6) 0.3384(5) 0.0459(2) 0.0507(13) Uani 1 1 d . . .
O2 O -0.0524(7) 0.1096(4) 0.0289(2) 0.0913(19) Uani 1 1 d . . .
N3 N 0.1991(7) 0.7856(5) -0.0616(2) 0.0518(14) Uani 1 1 d . . .
C3 C -0.0122(8) 0.3074(6) -0.0051(3) 0.0543(17) Uani 1 1 d . . .
N4 N 0.0476(6) 0.7913(5) -0.0825(3) 0.0660(18) Uani 1 1 d . . .
C4 C -0.0098(7) 0.3970(6) -0.0444(3) 0.0492(15) Uani 1 1 d . . .
H4A H -0.0487 0.3937 -0.0822 0.059 Uiso 1 1 calc R . .
C5 C 0.0607(7) 0.4920(6) -0.0175(3) 0.0449(14) Uani 1 1 d . . .
C6 C -0.0817(7) 0.1892(7) -0.0146(3) 0.0563(17) Uani 1 1 d . . .
C7 C -0.1434(11) -0.0052(7) 0.0225(4) 0.082(2) Uani 1 1 d . . .
H7A H -0.2527 0.0088 0.0300 0.098 Uiso 1 1 calc R . .
H7B H -0.1384 -0.0366 -0.0160 0.098 Uiso 1 1 calc R . .
C8 C -0.0763(14) -0.0873(8) 0.0616(5) 0.115(4) Uani 1 1 d . . .
H8A H -0.1324 -0.1629 0.0588 0.173 Uiso 1 1 calc R . .
H8B H -0.0817 -0.0551 0.0994 0.173 Uiso 1 1 calc R . .
H8C H 0.0316 -0.1006 0.0536 0.173 Uiso 1 1 calc R . .
C9 C 0.1637(7) 0.5216(6) 0.0841(3) 0.0465(15) Uani 1 1 d . . .
C10 C 0.2872(9) 0.4754(7) 0.1159(3) 0.0629(19) Uani 1 1 d . . .
H10B H 0.3306 0.4005 0.1073 0.076 Uiso 1 1 calc R . .
C11 C 0.3472(11) 0.5445(8) 0.1621(3) 0.074(2) Uani 1 1 d . . .
H11C H 0.4312 0.5136 0.1846 0.089 Uiso 1 1 calc R . .
C12 C 0.2921(11) 0.6474(9) 0.1746(3) 0.076(2) Uani 1 1 d . . .
H12B H 0.3395 0.6917 0.2045 0.091 Uiso 1 1 calc R . .
C13 C 0.1643(12) 0.6939(7) 0.1447(3) 0.073(2) Uani 1 1 d . . .
H13 H 0.1222 0.7679 0.1554 0.088 Uiso 1 1 calc R . .
C14 C 0.0979(9) 0.6323(7) 0.0989(3) 0.0596(18) Uani 1 1 d . . .
H14B H 0.0108 0.6635 0.0782 0.072 Uiso 1 1 calc R . .
C15 C -0.0144(8) 0.6881(6) -0.0685(3) 0.0583(18) Uani 1 1 d . . .
H15B H -0.1181 0.6660 -0.0777 0.070 Uiso 1 1 calc R . .
C16 C 0.0937(7) 0.6154(5) -0.0381(3) 0.0449(14) Uani 1 1 d . . .
C17 C 0.2286(7) 0.6786(6) -0.0348(3) 0.0436(13) Uani 1 1 d . . .
C18 C 0.3831(7) 0.6407(6) -0.0096(3) 0.0442(13) Uani 1 1 d . . .
C19 C 0.4479(8) 0.5336(7) -0.0298(3) 0.0573(17) Uani 1 1 d . . .
H19B H 0.3960 0.4907 -0.0593 0.069 Uiso 1 1 calc R . .
C20 C 0.5853(10) 0.4928(9) -0.0065(4) 0.076(2) Uani 1 1 d . . .
H20A H 0.6286 0.4220 -0.0206 0.092 Uiso 1 1 calc R . .
C21 C 0.6631(9) 0.5534(8) 0.0378(4) 0.076(2) Uani 1 1 d . . .
H21B H 0.7585 0.5241 0.0533 0.091 Uiso 1 1 calc R . .
C22 C 0.5997(9) 0.6566(8) 0.0587(3) 0.070(2) Uani 1 1 d . . .
H22B H 0.6507 0.6974 0.0891 0.084 Uiso 1 1 calc R . .
C23 C 0.4595(8) 0.7004(7) 0.0346(3) 0.0568(18) Uani 1 1 d . . .
H23B H 0.4167 0.7714 0.0487 0.068 Uiso 1 1 calc R . .
C24 C 0.2963(8) 0.8877(6) -0.0705(3) 0.0513(16) Uani 1 1 d . . .
C25 C 0.2270(10) 1.0020(7) -0.0715(3) 0.067(2) Uani 1 1 d . . .
H25B H 0.1201 1.0102 -0.0663 0.080 Uiso 1 1 calc R . .
C26 C 0.3170(11) 1.1021(7) -0.0800(3) 0.075(2) Uani 1 1 d . . .
H26B H 0.2705 1.1786 -0.0816 0.090 Uiso 1 1 calc R . .
C27 C 0.4763(11) 1.0910(8) -0.0863(3) 0.077(2) Uani 1 1 d . . .
H27B H 0.5377 1.1596 -0.0915 0.092 Uiso 1 1 calc R . .
C28 C 0.5423(10) 0.9786(8) -0.0848(3) 0.068(2) Uani 1 1 d . . .
H28A H 0.6499 0.9712 -0.0887 0.081 Uiso 1 1 calc R . .
C29 C 0.4552(8) 0.8761(7) -0.0775(3) 0.0551(17) Uani 1 1 d . . .
H29B H 0.5023 0.7998 -0.0773 0.066 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A N2A 1.322(7) . ?
N1A C5A 1.366(8) . ?
N1A C9A 1.426(7) . ?
O1A C6A 1.177(9) . ?
N2A C3A 1.313(8) . ?
O2A C6A 1.262(9) . ?
O2A C7A 1.423(8) . ?
O2A C7B 1.652(15) . ?
N3A N4A 1.346(7) . ?
N3A C17A 1.362(8) . ?
N3A C24A 1.420(8) . ?
C3A C4A 1.415(9) . ?
C3A C6A 1.475(9) . ?
N4A C15A 1.308(9) . ?
C4A C5A 1.367(9) . ?
C4A H4AA 0.9300 . ?
C5A C16A 1.429(9) . ?
C7B C8B 1.46(2) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7A C8A 1.471(13) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A C14A 1.340(10) . ?
C9A C10A 1.368(9) . ?
C10A C11B 1.331(10) . ?
C10A H10A 0.9300 . ?
C11B C12A 1.463(12) . ?
C11B H11A 0.9300 . ?
C12A C13A 1.343(12) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.384(11) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A C16A 1.385(9) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.391(9) . ?
C17A C18A 1.451(8) . ?
C18A C19A 1.363(10) . ?
C18A C23A 1.384(9) . ?
C19A C20A 1.384(9) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.353(12) . ?
C20A H20B 0.9300 . ?
C21A C22A 1.374(14) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.365(11) . ?
C22A H22A 0.9300 . ?
C23A H23A 0.9300 . ?
C24A C29A 1.357(10) . ?
C24A C25A 1.365(10) . ?
C25A C26A 1.388(10) . ?
C25A H25A 0.9300 . ?
C26A C27A 1.375(12) . ?
C26A H26A 0.9300 . ?
C27A C28A 1.329(13) . ?
C27A H27A 0.9300 . ?
C28A C29A 1.392(11) . ?
C28A H28B 0.9300 . ?
C29A H29A 0.9300 . ?
N1 C5 1.361(8) . ?
N1 N2 1.362(7) . ?
N1 C9 1.413(8) . ?
O1 C6 1.205(9) . ?
N2 C3 1.337(9) . ?
O2 C6 1.358(9) . ?
O2 C7 1.485(8) . ?
N3 C17 1.352(8) . ?
N3 N4 1.356(7) . ?
N3 C24 1.417(9) . ?
C3 C4 1.352(10) . ?
C3 C6 1.441(10) . ?
N4 C15 1.302(9) . ?
C4 C5 1.346(9) . ?
C4 H4A 0.9300 . ?
C5 C16 1.473(8) . ?
C7 C8 1.387(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.354(9) . ?
C9 C14 1.393(10) . ?
C10 C11 1.398(10) . ?
C10 H10B 0.9300 . ?
C11 C12 1.266(12) . ?
C11 H11C 0.9300 . ?
C12 C13 1.362(13) . ?
C12 H12B 0.9300 . ?
C13 C14 1.366(11) . ?
C13 H13 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.387(8) . ?
C15 H15B 0.9300 . ?
C16 C17 1.341(9) . ?
C17 C18 1.474(8) . ?
C18 C23 1.362(9) . ?
C18 C19 1.395(10) . ?
C19 C20 1.341(10) . ?
C19 H19B 0.9300 . ?
C20 C21 1.374(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.360(13) . ?
C21 H21B 0.9300 . ?
C22 C23 1.380(10) . ?
C22 H22B 0.9300 . ?
C23 H23B 0.9300 . ?
C24 C29 1.380(10) . ?
C24 C25 1.388(11) . ?
C25 C26 1.363(11) . ?
C25 H25B 0.9300 . ?
C26 C27 1.379(13) . ?
C26 H26B 0.9300 . ?
C27 C28 1.358(12) . ?
C27 H27B 0.9300 . ?
C28 C29 1.365(10) . ?
C28 H28A 0.9300 . ?
C29 H29B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2A N1A C5A 112.9(5) . . ?
N2A N1A C9A 119.9(5) . . ?
C5A N1A C9A 127.1(5) . . ?
C3A N2A N1A 105.8(5) . . ?
C6A O2A C7A 114.4(6) . . ?
C6A O2A C7B 123.9(7) . . ?
C7A O2A C7B 36.1(7) . . ?
N4A N3A C17A 112.3(5) . . ?
N4A N3A C24A 117.6(5) . . ?
C17A N3A C24A 130.1(6) . . ?
N2A C3A C4A 110.6(5) . . ?
N2A C3A C6A 124.4(6) . . ?
C4A C3A C6A 124.9(6) . . ?
C15A N4A N3A 104.4(5) . . ?
C5A C4A C3A 105.3(6) . . ?
C5A C4A H4AA 127.3 . . ?
C3A C4A H4AA 127.3 . . ?
N1A C5A C4A 105.3(5) . . ?
N1A C5A C16A 125.9(5) . . ?
C4A C5A C16A 128.8(5) . . ?
O1A C6A O2A 125.8(7) . . ?
O1A C6A C3A 120.6(7) . . ?
O2A C6A C3A 113.3(6) . . ?
C8B C7B O2A 90.7(12) . . ?
C8B C7B H7BA 113.5 . . ?
O2A C7B H7BA 113.5 . . ?
C8B C7B H7BB 113.5 . . ?
O2A C7B H7BB 113.5 . . ?
H7BA C7B H7BB 110.8 . . ?
O2A C7A C8A 107.3(6) . . ?
O2A C7A H7AA 110.3 . . ?
C8A C7A H7AA 110.3 . . ?
O2A C7A H7AB 110.3 . . ?
C8A C7A H7AB 110.3 . . ?
H7AA C7A H7AB 108.5 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C14A C9A C10A 121.5(6) . . ?
C14A C9A N1A 119.9(6) . . ?
C10A C9A N1A 118.6(6) . . ?
C11B C10A C9A 120.6(7) . . ?
C11B C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C10A C11B C12A 118.6(7) . . ?
C10A C11B H11A 120.7 . . ?
C12A C11B H11A 120.7 . . ?
C13A C12A C11B 119.1(7) . . ?
C13A C12A H12A 120.4 . . ?
C11B C12A H12A 120.4 . . ?
C12A C13A C14A 119.9(8) . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A H13A 120.1 . . ?
C9A C14A C13A 120.3(7) . . ?
C9A C14A H14A 119.9 . . ?
C13A C14A H14A 119.9 . . ?
N4A C15A C16A 113.5(6) . . ?
N4A C15A H15A 123.3 . . ?
C16A C15A H15A 123.3 . . ?
C15A C16A C17A 104.1(6) . . ?
C15A C16A C5A 126.8(6) . . ?
C17A C16A C5A 129.1(5) . . ?
N3A C17A C16A 105.7(5) . . ?
N3A C17A C18A 127.1(6) . . ?
C16A C17A C18A 127.2(6) . . ?
C19A C18A C23A 119.6(6) . . ?
C19A C18A C17A 119.0(6) . . ?
C23A C18A C17A 121.4(6) . . ?
C18A C19A C20A 121.7(7) . . ?
C18A C19A H19A 119.2 . . ?
C20A C19A H19A 119.2 . . ?
C21A C20A C19A 118.4(9) . . ?
C21A C20A H20B 120.8 . . ?
C19A C20A H20B 120.8 . . ?
C20A C21A C22A 120.5(7) . . ?
C20A C21A H21A 119.7 . . ?
C22A C21A H21A 119.7 . . ?
C23A C22A C21A 121.4(8) . . ?
C23A C22A H22A 119.3 . . ?
C21A C22A H22A 119.3 . . ?
C22A C23A C18A 118.5(8) . . ?
C22A C23A H23A 120.8 . . ?
C18A C23A H23A 120.8 . . ?
C29A C24A C25A 120.2(7) . . ?
C29A C24A N3A 118.8(7) . . ?
C25A C24A N3A 121.0(6) . . ?
C24A C25A C26A 119.1(7) . . ?
C24A C25A H25A 120.4 . . ?
C26A C25A H25A 120.4 . . ?
C27A C26A C25A 119.9(8) . . ?
C27A C26A H26A 120.1 . . ?
C25A C26A H26A 120.1 . . ?
C28A C27A C26A 120.6(7) . . ?
C28A C27A H27A 119.7 . . ?
C26A C27A H27A 119.7 . . ?
C27A C28A C29A 120.0(8) . . ?
C27A C28A H28B 120.0 . . ?
C29A C28A H28B 120.0 . . ?
C24A C29A C28A 120.1(8) . . ?
C24A C29A H29A 119.9 . . ?
C28A C29A H29A 119.9 . . ?
C5 N1 N2 111.9(5) . . ?
C5 N1 C9 130.1(5) . . ?
N2 N1 C9 117.9(5) . . ?
C3 N2 N1 102.0(6) . . ?
C6 O2 C7 113.5(6) . . ?
C17 N3 N4 110.9(6) . . ?
C17 N3 C24 131.5(6) . . ?
N4 N3 C24 117.5(6) . . ?
N2 C3 C4 113.9(6) . . ?
N2 C3 C6 121.1(7) . . ?
C4 C3 C6 125.0(6) . . ?
C15 N4 N3 105.0(5) . . ?
C5 C4 C3 105.6(6) . . ?
C5 C4 H4A 127.2 . . ?
C3 C4 H4A 127.2 . . ?
C4 C5 N1 106.6(5) . . ?
C4 C5 C16 130.4(6) . . ?
N1 C5 C16 122.9(5) . . ?
O1 C6 O2 121.3(7) . . ?
O1 C6 C3 124.1(7) . . ?
O2 C6 C3 114.1(6) . . ?
C8 C7 O2 107.0(7) . . ?
C8 C7 H7A 110.3 . . ?
O2 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
O2 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.0(6) . . ?
C10 C9 N1 120.2(6) . . ?
C14 C9 N1 119.7(6) . . ?
C9 C10 C11 117.6(8) . . ?
C9 C10 H10B 121.2 . . ?
C11 C10 H10B 121.2 . . ?
C12 C11 C10 122.8(8) . . ?
C12 C11 H11C 118.6 . . ?
C10 C11 H11C 118.6 . . ?
C11 C12 C13 120.9(8) . . ?
C11 C12 H12B 119.6 . . ?
C13 C12 H12B 119.6 . . ?
C12 C13 C14 120.2(8) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 118.4(7) . . ?
C13 C14 H14B 120.8 . . ?
C9 C14 H14B 120.8 . . ?
N4 C15 C16 111.5(6) . . ?
N4 C15 H15B 124.3 . . ?
C16 C15 H15B 124.3 . . ?
C17 C16 C15 105.8(6) . . ?
C17 C16 C5 129.6(6) . . ?
C15 C16 C5 124.5(6) . . ?
C16 C17 N3 106.7(5) . . ?
C16 C17 C18 128.3(6) . . ?
N3 C17 C18 124.9(6) . . ?
C23 C18 C19 119.0(7) . . ?
C23 C18 C17 123.2(7) . . ?
C19 C18 C17 117.6(6) . . ?
C20 C19 C18 119.8(7) . . ?
C20 C19 H19B 120.1 . . ?
C18 C19 H19B 120.1 . . ?
C19 C20 C21 121.2(8) . . ?
C19 C20 H20A 119.4 . . ?
C21 C20 H20A 119.4 . . ?
C22 C21 C20 119.6(7) . . ?
C22 C21 H21B 120.2 . . ?
C20 C21 H21B 120.2 . . ?
C21 C22 C23 119.8(7) . . ?
C21 C22 H22B 120.1 . . ?
C23 C22 H22B 120.1 . . ?
C18 C23 C22 120.6(8) . . ?
C18 C23 H23B 119.7 . . ?
C22 C23 H23B 119.7 . . ?
C29 C24 C25 120.1(6) . . ?
C29 C24 N3 122.0(6) . . ?
C25 C24 N3 117.9(7) . . ?
C26 C25 C24 119.5(8) . . ?
C26 C25 H25B 120.3 . . ?
C24 C25 H25B 120.3 . . ?
C25 C26 C27 120.7(9) . . ?
C25 C26 H26B 119.7 . . ?
C27 C26 H26B 119.7 . . ?
C28 C27 C26 119.1(8) . . ?
C28 C27 H27B 120.5 . . ?
C26 C27 H27B 120.5 . . ?
C27 C28 C29 121.8(8) . . ?
C27 C28 H28A 119.1 . . ?
C29 C28 H28A 119.1 . . ?
C28 C29 C24 118.9(7) . . ?
C28 C29 H29B 120.6 . . ?
C24 C29 H29B 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A N2A C3A -0.6(7) . . . . ?
C9A N1A N2A C3A 175.9(6) . . . . ?
N1A N2A C3A C4A 0.3(7) . . . . ?
N1A N2A C3A C6A -177.3(6) . . . . ?
C17A N3A N4A C15A 0.3(8) . . . . ?
C24A N3A N4A C15A -179.1(6) . . . . ?
N2A C3A C4A C5A 0.1(8) . . . . ?
C6A C3A C4A C5A 177.7(6) . . . . ?
N2A N1A C5A C4A 0.7(7) . . . . ?
C9A N1A C5A C4A -175.5(6) . . . . ?
N2A N1A C5A C16A 179.8(6) . . . . ?
C9A N1A C5A C16A 3.6(10) . . . . ?
C3A C4A C5A N1A -0.5(7) . . . . ?
C3A C4A C5A C16A -179.6(6) . . . . ?
C7A O2A C6A O1A 2.5(12) . . . . ?
C7B O2A C6A O1A 42.7(14) . . . . ?
C7A O2A C6A C3A 176.4(6) . . . . ?
C7B O2A C6A C3A -143.4(8) . . . . ?
N2A C3A C6A O1A 170.9(8) . . . . ?
C4A C3A C6A O1A -6.3(12) . . . . ?
N2A C3A C6A O2A -3.4(10) . . . . ?
C4A C3A C6A O2A 179.4(6) . . . . ?
C6A O2A C7B C8B -118.1(10) . . . . ?
C7A O2A C7B C8B -32.5(10) . . . . ?
C6A O2A C7A C8A 161.3(7) . . . . ?
C7B O2A C7A C8A 46.6(11) . . . . ?
N2A N1A C9A C14A -126.4(7) . . . . ?
C5A N1A C9A C14A 49.5(10) . . . . ?
N2A N1A C9A C10A 54.0(9) . . . . ?
C5A N1A C9A C10A -130.0(7) . . . . ?
C14A C9A C10A C11B 1.0(12) . . . . ?
N1A C9A C10A C11B -179.5(7) . . . . ?
C9A C10A C11B C12A 0.1(13) . . . . ?
C10A C11B C12A C13A -2.2(13) . . . . ?
C11B C12A C13A C14A 3.2(13) . . . . ?
C10A C9A C14A C13A 0.0(11) . . . . ?
N1A C9A C14A C13A -179.5(7) . . . . ?
C12A C13A C14A C9A -2.2(13) . . . . ?
N3A N4A C15A C16A 0.2(8) . . . . ?
N4A C15A C16A C17A -0.6(9) . . . . ?
N4A C15A C16A C5A -179.8(6) . . . . ?
N1A C5A C16A C15A -129.2(8) . . . . ?
C4A C5A C16A C15A 49.7(11) . . . . ?
N1A C5A C16A C17A 51.8(11) . . . . ?
C4A C5A C16A C17A -129.3(8) . . . . ?
N4A N3A C17A C16A -0.7(8) . . . . ?
C24A N3A C17A C16A 178.6(7) . . . . ?
N4A N3A C17A C18A 178.4(6) . . . . ?
C24A N3A C17A C18A -2.3(12) . . . . ?
C15A C16A C17A N3A 0.7(8) . . . . ?
C5A C16A C17A N3A 179.9(6) . . . . ?
C15A C16A C17A C18A -178.4(7) . . . . ?
C5A C16A C17A C18A 0.8(12) . . . . ?
N3A C17A C18A C19A -121.6(8) . . . . ?
C16A C17A C18A C19A 57.3(10) . . . . ?
N3A C17A C18A C23A 59.5(10) . . . . ?
C16A C17A C18A C23A -121.6(8) . . . . ?
C23A C18A C19A C20A 0.3(11) . . . . ?
C17A C18A C19A C20A -178.7(8) . . . . ?
C18A C19A C20A C21A 0.6(13) . . . . ?
C19A C20A C21A C22A -0.1(14) . . . . ?
C20A C21A C22A C23A -1.1(14) . . . . ?
C21A C22A C23A C18A 2.0(12) . . . . ?
C19A C18A C23A C22A -1.5(11) . . . . ?
C17A C18A C23A C22A 177.4(7) . . . . ?
N4A N3A C24A C29A 30.4(9) . . . . ?
C17A N3A C24A C29A -148.9(8) . . . . ?
N4A N3A C24A C25A -146.8(6) . . . . ?
C17A N3A C24A C25A 33.9(11) . . . . ?
C29A C24A C25A C26A 4.2(11) . . . . ?
N3A C24A C25A C26A -178.7(6) . . . . ?
C24A C25A C26A C27A -1.3(10) . . . . ?
C25A C26A C27A C28A -1.7(12) . . . . ?
C26A C27A C28A C29A 1.8(13) . . . . ?
C25A C24A C29A C28A -4.1(12) . . . . ?
N3A C24A C29A C28A 178.7(7) . . . . ?
C27A C28A C29A C24A 1.1(13) . . . . ?
C5 N1 N2 C3 -0.7(7) . . . . ?
C9 N1 N2 C3 176.2(6) . . . . ?
N1 N2 C3 C4 0.6(8) . . . . ?
N1 N2 C3 C6 -177.6(6) . . . . ?
C17 N3 N4 C15 -0.1(9) . . . . ?
C24 N3 N4 C15 -179.7(6) . . . . ?
N2 C3 C4 C5 -0.2(8) . . . . ?
C6 C3 C4 C5 177.9(6) . . . . ?
C3 C4 C5 N1 -0.2(7) . . . . ?
C3 C4 C5 C16 -178.7(6) . . . . ?
N2 N1 C5 C4 0.6(7) . . . . ?
C9 N1 C5 C4 -175.8(6) . . . . ?
N2 N1 C5 C16 179.2(6) . . . . ?
C9 N1 C5 C16 2.8(10) . . . . ?
C7 O2 C6 O1 -16.5(11) . . . . ?
C7 O2 C6 C3 171.5(6) . . . . ?
N2 C3 C6 O1 178.5(8) . . . . ?
C4 C3 C6 O1 0.5(12) . . . . ?
N2 C3 C6 O2 -9.8(9) . . . . ?
C4 C3 C6 O2 172.2(6) . . . . ?
C6 O2 C7 C8 166.3(8) . . . . ?
C5 N1 C9 C10 -131.1(7) . . . . ?
N2 N1 C9 C10 52.7(9) . . . . ?
C5 N1 C9 C14 51.3(10) . . . . ?
N2 N1 C9 C14 -124.9(7) . . . . ?
C14 C9 C10 C11 -2.0(11) . . . . ?
N1 C9 C10 C11 -179.5(7) . . . . ?
C9 C10 C11 C12 -0.8(14) . . . . ?
C10 C11 C12 C13 3.3(15) . . . . ?
C11 C12 C13 C14 -3.0(14) . . . . ?
C12 C13 C14 C9 0.2(13) . . . . ?
C10 C9 C14 C13 2.2(11) . . . . ?
N1 C9 C14 C13 179.8(7) . . . . ?
N3 N4 C15 C16 0.7(9) . . . . ?
N4 C15 C16 C17 -1.1(9) . . . . ?
N4 C15 C16 C5 -178.4(6) . . . . ?
C4 C5 C16 C17 -129.7(8) . . . . ?
N1 C5 C16 C17 52.0(10) . . . . ?
C4 C5 C16 C15 47.0(11) . . . . ?
N1 C5 C16 C15 -131.3(7) . . . . ?
C15 C16 C17 N3 0.9(8) . . . . ?
C5 C16 C17 N3 178.1(6) . . . . ?
C15 C16 C17 C18 -176.5(7) . . . . ?
C5 C16 C17 C18 0.6(12) . . . . ?
N4 N3 C17 C16 -0.5(8) . . . . ?
C24 N3 C17 C16 179.0(7) . . . . ?
N4 N3 C17 C18 177.1(7) . . . . ?
C24 N3 C17 C18 -3.5(12) . . . . ?
C16 C17 C18 C23 -119.7(9) . . . . ?
N3 C17 C18 C23 63.3(10) . . . . ?
C16 C17 C18 C19 55.8(10) . . . . ?
N3 C17 C18 C19 -121.3(8) . . . . ?
C23 C18 C19 C20 -1.6(11) . . . . ?
C17 C18 C19 C20 -177.2(7) . . . . ?
C18 C19 C20 C21 1.1(13) . . . . ?
C19 C20 C21 C22 0.3(14) . . . . ?
C20 C21 C22 C23 -1.1(13) . . . . ?
C19 C18 C23 C22 0.8(11) . . . . ?
C17 C18 C23 C22 176.2(7) . . . . ?
C21 C22 C23 C18 0.6(12) . . . . ?
C17 N3 C24 C29 32.6(12) . . . . ?
N4 N3 C24 C29 -147.9(7) . . . . ?
C17 N3 C24 C25 -146.7(8) . . . . ?
N4 N3 C24 C25 32.8(10) . . . . ?
C29 C24 C25 C26 0.8(12) . . . . ?
N3 C24 C25 C26 -179.9(7) . . . . ?
C24 C25 C26 C27 -1.6(13) . . . . ?
C25 C26 C27 C28 1.0(13) . . . . ?
C26 C27 C28 C29 0.4(12) . . . . ?
C27 C28 C29 C24 -1.2(10) . . . . ?
C25 C24 C29 C28 0.6(11) . . . . ?
N3 C24 C29 C28 -178.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_dc_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1569342'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"Ethyl 5'-(4-chlorophenyl)-1',2-diphenyl-1'H,2H-3,4'-bipyrazole-5-carboxylate "
_chemical_name_common            ?
_chemical_melting_point          406-407
_chemical_formula_moiety         'C27 H21 Cl N4 O2'
_chemical_formula_sum            'C27 H21 Cl N4 O2'
_chemical_formula_weight         468.93

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'
Cl Cl 0.3639 0.7018 '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'

_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                   8.803(6)
_cell_length_b                   10.863(6)
_cell_length_c                   12.961(11)
_cell_angle_alpha                84.40(6)
_cell_angle_beta                 71.46(7)
_cell_angle_gamma                80.99(5)
_cell_volume                     1159.1(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7278
_cell_measurement_theta_min      3.5899
_cell_measurement_theta_max      65.3191

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_min  0.60462
_exptl_absorpt_correction_T_max  1.29544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13646
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         66.09
_reflns_number_total             3935
_reflns_number_gt                3040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1040P)²+0.0000P] where P=(Fo²+2Fc²)/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         3935
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
Cl1 Cl 0.36530(7) 0.80183(5) 0.27094(4) 0.0658(2) Uani 1 1 d . . .
N1 N 1.00359(19) 1.13711(14) -0.20806(12) 0.0450(4) Uani 1 1 d . . .
O1 O 0.7061(4) 1.53978(19) 0.32541(17) 0.1307(11) Uani 1 1 d . . .
C1 C 0.7224(4) 1.3616(3) 0.47568(19) 0.0936(9) Uani 1 1 d . . .
H1A H 0.6579 1.4420 0.4939 0.112 Uiso 1 1 calc R . .
H1B H 0.6655 1.2980 0.5236 0.112 Uiso 1 1 calc R . .
N2 N 0.91796(19) 1.04782(13) -0.14908(12) 0.0454(4) Uani 1 1 d . . .
O2 O 0.7428(3) 1.33845(16) 0.36280(12) 0.0803(5) Uani 1 1 d . . .
C2 C 0.8788(5) 1.3601(4) 0.4923(2) 0.1187(13) Uani 1 1 d . . .
H2A H 0.8630 1.3754 0.5669 0.178 Uiso 1 1 calc R . .
H2B H 0.9344 1.4240 0.4457 0.178 Uiso 1 1 calc R . .
H2C H 0.9420 1.2802 0.4751 0.178 Uiso 1 1 calc R . .
N3 N 0.77125(18) 1.43321(13) 0.02057(12) 0.0429(4) Uani 1 1 d . . .
C3 C 0.8289(2) 1.09926(16) -0.05580(14) 0.0410(4) Uani 1 1 d . . .
N4 N 0.7440(2) 1.49261(14) 0.11265(12) 0.0489(4) Uani 1 1 d . . .
C4 C 0.8592(2) 1.22289(16) -0.05551(14) 0.0423(4) Uani 1 1 d . . .
C5 C 0.9710(2) 1.24300(17) -0.15435(15) 0.0460(4) Uani 1 1 d . . .
C6 C 0.7572(2) 1.40175(18) 0.18623(15) 0.0479(4) Uani 1 1 d . . .
C7 C 0.7931(2) 1.28459(18) 0.14216(15) 0.0474(4) Uani 1 1 d . . .
C8 C 0.8038(2) 1.30671(15) 0.03475(14) 0.0416(4) Uani 1 1 d . . .
C9 C 1.1107(2) 1.11492(18) -0.31496(15) 0.0487(4) Uani 1 1 d . . .
C10 C 1.0931(4) 1.0187(2) -0.3699(2) 0.0794(7) Uani 1 1 d . . .
H10A H 1.0136 0.9676 -0.3374 0.095 Uiso 1 1 calc R . .
C11 C 1.1959(4) 0.9993(3) -0.4745(2) 0.0966(10) Uani 1 1 d . . .
H11A H 1.1841 0.9350 -0.5125 0.116 Uiso 1 1 calc R . .
C12 C 1.3141(3) 1.0725(3) -0.52263(19) 0.0801(8) Uani 1 1 d . . .
H12A H 1.3836 1.0578 -0.5925 0.096 Uiso 1 1 calc R . .
C13 C 1.3289(3) 1.1670(3) -0.46731(19) 0.0791(7) Uani 1 1 d . . .
H13A H 1.4081 1.2183 -0.5001 0.095 Uiso 1 1 calc R . .
C14 C 1.2279(3) 1.1884(2) -0.36273(18) 0.0681(6) Uani 1 1 d . . .
H14A H 1.2403 1.2530 -0.3252 0.082 Uiso 1 1 calc R . .
C15 C 0.7575(2) 1.50511(16) -0.07406(14) 0.0436(4) Uani 1 1 d . . .
C16 C 0.6668(3) 1.4704(2) -0.13290(17) 0.0563(5) Uani 1 1 d . . .
H16A H 0.6135 1.4004 -0.1110 0.068 Uiso 1 1 calc R . .
C17 C 0.6570(3) 1.5420(3) -0.22484(19) 0.0707(6) Uani 1 1 d . . .
H17A H 0.5982 1.5193 -0.2666 0.085 Uiso 1 1 calc R . .
C18 C 0.7332(3) 1.6464(3) -0.2552(2) 0.0770(7) Uani 1 1 d . . .
H18A H 0.7253 1.6945 -0.3172 0.092 Uiso 1 1 calc R . .
C19 C 0.8207(3) 1.6803(2) -0.1952(2) 0.0724(6) Uani 1 1 d . . .
H19A H 0.8718 1.7515 -0.2163 0.087 Uiso 1 1 calc R . .
C20 C 0.8336(3) 1.60970(18) -0.10393(17) 0.0540(5) Uani 1 1 d . . .
H20A H 0.8932 1.6325 -0.0628 0.065 Uiso 1 1 calc R . .
C21 C 0.7162(2) 1.02753(16) 0.02706(14) 0.0405(4) Uani 1 1 d . . .
C27 C 0.7339(3) 1.4362(2) 0.29711(18) 0.0622(6) Uani 1 1 d . . .
C22 C 0.5678(2) 1.08428(17) 0.09164(15) 0.0461(4) Uani 1 1 d . . .
H22A H 0.5409 1.1702 0.0841 0.055 Uiso 1 1 calc R . .
C23 C 0.4607(2) 1.01557(18) 0.16624(15) 0.0490(4) Uani 1 1 d . . .
H23A H 0.3618 1.0542 0.2089 0.059 Uiso 1 1 calc R . .
C24 C 0.5018(2) 0.88864(17) 0.17691(14) 0.0466(4) Uani 1 1 d . . .
C25 C 0.6460(2) 0.82914(17) 0.11405(15) 0.0491(4) Uani 1 1 d . . .
H25A H 0.6715 0.7431 0.1217 0.059 Uiso 1 1 calc R . .
C26 C 0.7525(2) 0.89958(17) 0.03916(15) 0.0465(4) Uani 1 1 d . . .
H26A H 0.8506 0.8601 -0.0039 0.056 Uiso 1 1 calc R . .
H5 H 1.023(3) 1.313(2) -0.1852(17) 0.052(5) Uiso 1 1 d . . .
H7 H 0.812(3) 1.210(2) 0.1788(17) 0.053(6) 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 C24 1.737(2) . ?
N1 N2 1.346(2) . ?
N1 C5 1.348(3) . ?
N1 C9 1.425(3) . ?
O1 C27 1.183(3) . ?
C1 C2 1.457(5) . ?
C1 O2 1.458(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N2 C3 1.334(3) . ?
O2 C27 1.303(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N3 N4 1.348(2) . ?
N3 C8 1.366(2) . ?
N3 C15 1.417(3) . ?
C3 C4 1.410(3) . ?
C3 C21 1.465(3) . ?
N4 C6 1.322(3) . ?
C4 C5 1.367(3) . ?
C4 C8 1.463(3) . ?
C5 H5 0.94(2) . ?
C6 C7 1.395(3) . ?
C6 C27 1.463(3) . ?
C7 C8 1.365(3) . ?
C7 H7 0.92(2) . ?
C9 C14 1.357(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.384(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.352(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.383(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C20 1.370(3) . ?
C15 C16 1.378(3) . ?
C16 C17 1.377(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C26 1.382(3) . ?
C21 C22 1.393(3) . ?
C22 C23 1.372(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.375(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.371(3) . ?
C25 C26 1.381(3) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 111.89(15) . . ?
N2 N1 C9 120.61(15) . . ?
C5 N1 C9 127.48(17) . . ?
C2 C1 O2 110.7(3) . . ?
C2 C1 H1A 109.5 . . ?
O2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C3 N2 N1 105.28(15) . . ?
C27 O2 C1 116.8(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 N3 C8 112.66(15) . . ?
N4 N3 C15 118.48(15) . . ?
C8 N3 C15 128.82(15) . . ?
N2 C3 C4 110.68(17) . . ?
N2 C3 C21 119.66(16) . . ?
C4 C3 C21 129.64(16) . . ?
C6 N4 N3 104.24(15) . . ?
C5 C4 C3 104.79(17) . . ?
C5 C4 C8 126.16(17) . . ?
C3 C4 C8 128.51(17) . . ?
N1 C5 C4 107.36(18) . . ?
N1 C5 H5 121.5(12) . . ?
C4 C5 H5 131.2(12) . . ?
N4 C6 C7 111.88(18) . . ?
N4 C6 C27 117.85(18) . . ?
C7 C6 C27 130.27(19) . . ?
C8 C7 C6 105.67(18) . . ?
C8 C7 H7 128.8(13) . . ?
C6 C7 H7 125.4(13) . . ?
C7 C8 N3 105.53(16) . . ?
C7 C8 C4 130.82(17) . . ?
N3 C8 C4 123.15(16) . . ?
C14 C9 C10 120.2(2) . . ?
C14 C9 N1 120.59(18) . . ?
C10 C9 N1 119.2(2) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C9 C14 C13 119.8(2) . . ?
C9 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C20 C15 C16 121.41(19) . . ?
C20 C15 N3 118.64(18) . . ?
C16 C15 N3 119.94(18) . . ?
C17 C16 C15 118.4(2) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C15 C20 C19 119.2(2) . . ?
C15 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C26 C21 C22 118.31(18) . . ?
C26 C21 C3 120.03(17) . . ?
C22 C21 C3 121.59(16) . . ?
O1 C27 O2 123.4(2) . . ?
O1 C27 C6 124.6(2) . . ?
O2 C27 C6 111.92(19) . . ?
C23 C22 C21 121.12(18) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C22 C23 C24 118.95(18) . . ?
C22 C23 H23A 120.5 . . ?
C24 C23 H23A 120.5 . . ?
C25 C24 C23 121.67(18) . . ?
C25 C24 Cl1 119.50(16) . . ?
C23 C24 Cl1 118.82(16) . . ?
C24 C25 C26 118.70(18) . . ?
C24 C25 H25A 120.7 . . ?
C26 C25 H25A 120.7 . . ?
C25 C26 C21 121.24(18) . . ?
C25 C26 H26A 119.4 . . ?
C21 C26 H26A 119.4 . . ?

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
C5 N1 N2 C3 0.1(2) . . . . ?
C9 N1 N2 C3 -178.65(16) . . . . ?
C2 C1 O2 C27 -94.7(4) . . . . ?
N1 N2 C3 C4 -0.3(2) . . . . ?
N1 N2 C3 C21 178.17(15) . . . . ?
C8 N3 N4 C6 -0.9(2) . . . . ?
C15 N3 N4 C6 176.81(16) . . . . ?
N2 C3 C4 C5 0.4(2) . . . . ?
C21 C3 C4 C5 -177.90(18) . . . . ?
N2 C3 C4 C8 -171.50(17) . . . . ?
C21 C3 C4 C8 10.2(3) . . . . ?
N2 N1 C5 C4 0.1(2) . . . . ?
C9 N1 C5 C4 178.77(18) . . . . ?
C3 C4 C5 N1 -0.3(2) . . . . ?
C8 C4 C5 N1 171.83(17) . . . . ?
N3 N4 C6 C7 0.2(2) . . . . ?
N3 N4 C6 C27 179.93(17) . . . . ?
N4 C6 C7 C8 0.6(2) . . . . ?
C27 C6 C7 C8 -179.1(2) . . . . ?
C6 C7 C8 N3 -1.1(2) . . . . ?
C6 C7 C8 C4 170.70(18) . . . . ?
N4 N3 C8 C7 1.3(2) . . . . ?
C15 N3 C8 C7 -176.11(17) . . . . ?
N4 N3 C8 C4 -171.29(16) . . . . ?
C15 N3 C8 C4 11.3(3) . . . . ?
C5 C4 C8 C7 -128.9(2) . . . . ?
C3 C4 C8 C7 41.4(3) . . . . ?
C5 C4 C8 N3 41.7(3) . . . . ?
C3 C4 C8 N3 -148.05(19) . . . . ?
N2 N1 C9 C14 -161.9(2) . . . . ?
C5 N1 C9 C14 19.5(3) . . . . ?
N2 N1 C9 C10 18.7(3) . . . . ?
C5 N1 C9 C10 -159.8(2) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
N1 C9 C10 C11 178.9(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C10 C9 C14 C13 0.5(4) . . . . ?
N1 C9 C14 C13 -178.8(2) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
N4 N3 C15 C20 48.2(2) . . . . ?
C8 N3 C15 C20 -134.4(2) . . . . ?
N4 N3 C15 C16 -130.69(19) . . . . ?
C8 N3 C15 C16 46.6(3) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
N3 C15 C16 C17 -179.58(18) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
N3 C15 C20 C19 -179.78(18) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
N2 C3 C21 C26 32.7(2) . . . . ?
C4 C3 C21 C26 -149.18(19) . . . . ?
N2 C3 C21 C22 -144.25(18) . . . . ?
C4 C3 C21 C22 33.9(3) . . . . ?
C1 O2 C27 O1 -2.3(4) . . . . ?
C1 O2 C27 C6 179.6(2) . . . . ?
N4 C6 C27 O1 -1.0(4) . . . . ?
C7 C6 C27 O1 178.7(3) . . . . ?
N4 C6 C27 O2 177.1(2) . . . . ?
C7 C6 C27 O2 -3.2(4) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C3 C21 C22 C23 177.61(16) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C22 C23 C24 Cl1 -179.65(14) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
Cl1 C24 C25 C26 179.55(14) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C22 C21 C26 C25 -0.7(3) . . . . ?
C3 C21 C26 C25 -177.75(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        66.09
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.089

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
