# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Chune Dong'
_publ_contact_author_email       cdong@whu.edu.cn

_publ_section_title              
;
Facile Synthesis of 1,3,4-Benzotriazepines
and 1-Arylamide-1H-indazoles via Palladium Catalyzed Cyclization
of Aryl Isocyanates and Aryl Hydrazones under Microwave Irradiation
;
_publ_author_name                'Chune Dong.'

# Attachment '- 91223xll_0m.cif'

data_91223xll_0m
_database_code_depnum_ccdc_archive 'CCDC 773012'
#TrackingRef '- 91223xll_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Cl N3 O'
_chemical_formula_weight         285.73

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   C2/c

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

_cell_length_a                   23.441(6)
_cell_length_b                   6.2204(15)
_cell_length_c                   18.816(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.452(4)
_cell_angle_gamma                90.00
_cell_volume                     2713.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_T_max  0.9258
_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  ?
_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            7436
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2666
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_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^)+(0.0450P)^2^+1.1296P] 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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2666
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.40753(7) 0.7412(3) 0.60456(8) 0.0626(4) Uani 1 1 d . . .
H1 H 0.3865 0.8656 0.6095 0.075 Uiso 1 1 calc R . .
C2 C 0.45187(8) 0.6777(3) 0.65642(9) 0.0755(5) Uani 1 1 d . . .
H2 H 0.4605 0.7609 0.6977 0.091 Uiso 1 1 calc R . .
C3 C 0.48416(8) 0.4939(4) 0.64943(10) 0.0772(6) Uani 1 1 d . . .
H3 H 0.5140 0.4575 0.6857 0.093 Uiso 1 1 calc R . .
C4 C 0.47280(7) 0.3662(3) 0.59026(10) 0.0675(5) Uani 1 1 d . . .
H4 H 0.4945 0.2433 0.5857 0.081 Uiso 1 1 calc R . .
C5 C 0.42761(6) 0.4246(3) 0.53647(8) 0.0531(4) Uani 1 1 d . . .
C6 C 0.39584(6) 0.6103(2) 0.54456(8) 0.0501(3) Uani 1 1 d . . .
C8 C 0.40376(7) 0.3369(2) 0.46842(9) 0.0567(4) Uani 1 1 d . . .
C9 C 0.42266(9) 0.1394(3) 0.43401(12) 0.0796(5) Uani 1 1 d . . .
H9A H 0.3958 0.1070 0.3918 0.119 Uiso 1 1 calc R . .
H9B H 0.4241 0.0215 0.4671 0.119 Uiso 1 1 calc R . .
H9C H 0.4603 0.1622 0.4209 0.119 Uiso 1 1 calc R . .
C10 C 0.31471(6) 0.7869(2) 0.46481(7) 0.0494(3) Uani 1 1 d . . .
C11 C 0.24399(6) 0.9085(2) 0.36236(7) 0.0464(3) Uani 1 1 d . . .
C12 C 0.23258(7) 1.1089(3) 0.38964(8) 0.0552(4) Uani 1 1 d . . .
H12 H 0.2527 1.1544 0.4333 0.066 Uiso 1 1 calc R . .
C13 C 0.19145(7) 1.2403(3) 0.35195(8) 0.0560(4) Uani 1 1 d . . .
H13 H 0.1837 1.3742 0.3703 0.067 Uiso 1 1 calc R . .
C14 C 0.16190(6) 1.1731(2) 0.28710(8) 0.0504(4) Uani 1 1 d . . .
C15 C 0.17270(6) 0.9756(3) 0.25915(8) 0.0521(4) Uani 1 1 d . . .
H15 H 0.1525 0.9313 0.2153 0.062 Uiso 1 1 calc R . .
C16 C 0.21381(6) 0.8440(2) 0.29682(7) 0.0499(3) Uani 1 1 d . . .
H16 H 0.2214 0.7104 0.2781 0.060 Uiso 1 1 calc R . .
Cl1 Cl 0.110845(19) 1.34338(7) 0.23948(2) 0.07335(18) Uani 1 1 d . . .
N1 N 0.35558(5) 0.6248(2) 0.48283(6) 0.0518(3) Uani 1 1 d . . .
N2 N 0.28603(5) 0.7672(2) 0.39741(6) 0.0525(3) Uani 1 1 d . . .
H2A H 0.2943 0.6569 0.3733 0.063 Uiso 1 1 calc R . .
N3 N 0.36151(5) 0.4559(2) 0.43662(7) 0.0563(3) Uani 1 1 d . . .
O2 O 0.30865(5) 0.92784(19) 0.50746(5) 0.0641(3) Uani 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 0.0575(9) 0.0808(11) 0.0480(8) -0.0012(8) 0.0023(7) 0.0207(8)
C2 0.0675(11) 0.1042(15) 0.0509(9) -0.0019(9) -0.0041(8) 0.0221(10)
C3 0.0638(10) 0.1027(15) 0.0615(10) 0.0152(10) -0.0025(8) 0.0274(10)
C4 0.0592(10) 0.0734(11) 0.0701(11) 0.0181(9) 0.0101(8) 0.0227(8)
C5 0.0510(8) 0.0543(8) 0.0556(8) 0.0123(7) 0.0126(6) 0.0086(7)
C6 0.0452(7) 0.0595(9) 0.0456(7) 0.0089(7) 0.0071(6) 0.0086(7)
C8 0.0590(9) 0.0482(8) 0.0640(10) 0.0063(7) 0.0131(7) 0.0070(7)
C9 0.0892(13) 0.0570(10) 0.0929(14) -0.0056(10) 0.0145(11) 0.0149(10)
C10 0.0481(8) 0.0565(8) 0.0434(7) 0.0017(7) 0.0058(6) 0.0080(6)
C11 0.0437(7) 0.0520(8) 0.0428(7) 0.0009(6) 0.0044(5) 0.0031(6)
C12 0.0569(9) 0.0589(9) 0.0457(8) -0.0067(7) -0.0059(6) 0.0074(7)
C13 0.0602(9) 0.0519(9) 0.0532(8) -0.0039(7) -0.0010(7) 0.0092(7)
C14 0.0458(8) 0.0537(8) 0.0494(8) 0.0084(6) 0.0001(6) 0.0007(6)
C15 0.0513(8) 0.0591(9) 0.0430(7) 0.0014(7) -0.0024(6) -0.0067(7)
C16 0.0539(8) 0.0497(8) 0.0452(8) -0.0030(6) 0.0044(6) -0.0004(6)
Cl1 0.0703(3) 0.0683(3) 0.0731(3) 0.0124(2) -0.0169(2) 0.0106(2)
N1 0.0535(7) 0.0548(7) 0.0454(6) 0.0003(5) 0.0021(5) 0.0120(6)
N2 0.0553(7) 0.0554(7) 0.0447(6) -0.0051(6) -0.0001(5) 0.0128(6)
N3 0.0615(8) 0.0505(7) 0.0562(7) -0.0029(6) 0.0062(6) 0.0060(6)
O2 0.0693(7) 0.0728(7) 0.0461(6) -0.0083(5) -0.0046(5) 0.0255(6)

_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 C2 1.375(2) . ?
C1 C6 1.386(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 C8 1.428(2) . ?
C6 N1 1.3876(19) . ?
C8 N3 1.3086(19) . ?
C8 C9 1.486(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O2 1.2108(17) . ?
C10 N2 1.3508(19) . ?
C10 N1 1.3983(18) . ?
C11 C16 1.388(2) . ?
C11 C12 1.389(2) . ?
C11 N2 1.4097(18) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 Cl1 1.7441(15) . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N1 N3 1.3836(17) . ?
N2 H2A 0.8600 . ?

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 C1 C6 116.59(16) . . ?
C2 C1 H1 121.7 . . ?
C6 C1 H1 121.7 . . ?
C1 C2 C3 122.35(18) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 120.95(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.41(16) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 119.65(15) . . ?
C6 C5 C8 105.61(13) . . ?
C4 C5 C8 134.73(15) . . ?
C1 C6 N1 132.23(14) . . ?
C1 C6 C5 122.05(14) . . ?
N1 C6 C5 105.71(13) . . ?
N3 C8 C5 111.37(13) . . ?
N3 C8 C9 121.48(16) . . ?
C5 C8 C9 127.14(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N2 126.67(14) . . ?
O2 C10 N1 120.30(13) . . ?
N2 C10 N1 113.02(13) . . ?
C16 C11 C12 119.16(13) . . ?
C16 C11 N2 117.75(13) . . ?
C12 C11 N2 123.08(13) . . ?
C13 C12 C11 120.01(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.93(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.91(14) . . ?
C15 C14 Cl1 119.82(11) . . ?
C13 C14 Cl1 119.27(12) . . ?
C14 C15 C16 119.22(13) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 120.78(14) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N3 N1 C6 110.97(12) . . ?
N3 N1 C10 121.59(12) . . ?
C6 N1 C10 127.40(13) . . ?
C10 N2 C11 126.87(12) . . ?
C10 N2 H2A 116.6 . . ?
C11 N2 H2A 116.6 . . ?
C8 N3 N1 106.32(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C5 C8 179.02(18) . . . . ?
C2 C1 C6 N1 -179.36(16) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C8 C5 C6 C1 -178.97(15) . . . . ?
C4 C5 C6 N1 179.14(14) . . . . ?
C8 C5 C6 N1 0.04(15) . . . . ?
C6 C5 C8 N3 0.38(18) . . . . ?
C4 C5 C8 N3 -178.52(17) . . . . ?
C6 C5 C8 C9 179.41(16) . . . . ?
C4 C5 C8 C9 0.5(3) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
N2 C11 C12 C13 179.00(14) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 Cl1 -178.96(12) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
Cl1 C14 C15 C16 178.98(11) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
N2 C11 C16 C15 -179.05(13) . . . . ?
C1 C6 N1 N3 178.44(16) . . . . ?
C5 C6 N1 N3 -0.43(16) . . . . ?
C1 C6 N1 C10 0.7(3) . . . . ?
C5 C6 N1 C10 -178.19(14) . . . . ?
O2 C10 N1 N3 176.74(14) . . . . ?
N2 C10 N1 N3 -4.5(2) . . . . ?
O2 C10 N1 C6 -5.7(2) . . . . ?
N2 C10 N1 C6 173.09(14) . . . . ?
O2 C10 N2 C11 1.3(3) . . . . ?
N1 C10 N2 C11 -177.39(13) . . . . ?
C16 C11 N2 C10 -171.15(14) . . . . ?
C12 C11 N2 C10 10.3(2) . . . . ?
C5 C8 N3 N1 -0.63(17) . . . . ?
C9 C8 N3 N1 -179.73(15) . . . . ?
C6 N1 N3 C8 0.66(17) . . . . ?
C10 N1 N3 C8 178.58(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A N3 0.86 2.22 2.6537(18) 111.4 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.029