#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:58:40 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033008.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033008
loop_
_publ_author_name
'Chandrasekhar, Attoor'
'Sankararaman, Sethuraman'
_publ_section_title
;
 Selective Synthesis of 3-Arylbenzo-1,2,3-triazin-4(3H)-ones and
 1-Aryl-(1H)-benzo-1,2,3-triazoles from 1,3-Diaryltriazenes through Pd(0)
 Catalyzed Annulation Reactions.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11487
_journal_page_last               11493
_journal_paper_doi               10.1021/acs.joc.7b02023
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8573(6)
_cell_length_b                   11.8742(10)
_cell_length_c                   19.7672(19)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.91
_cell_measurement_theta_min      2.68
_cell_volume                     1609.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        23.063
_diffrn_reflns_theta_max         23.063
_diffrn_reflns_theta_min         2.061
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 583 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1724
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02023_si_002.cif
_cod_data_source_block           784
_cod_depositor_comments
'Adding full bibliography for 4033007--4033008.cif.'
_cod_database_code               4033008
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1483(8) -0.1523(3) 0.5362(2) 0.0742(13) Uani 1 1 d . . . . .
H1 H -0.0783 -0.2193 0.5373 0.089 Uiso 1 1 calc R U . . .
C2 C -0.3189(7) -0.1416(4) 0.5714(2) 0.0734(13) Uani 1 1 d . . . . .
H2 H -0.3644 -0.2026 0.5964 0.088 Uiso 1 1 calc R U . . .
C3 C -0.4263(6) -0.0424(4) 0.5710(2) 0.0598(11) Uani 1 1 d . . . . .
C4 C -0.3589(6) 0.0465(3) 0.53338(19) 0.0536(10) Uani 1 1 d . . . . .
H4 H -0.4296 0.1133 0.5324 0.064 Uiso 1 1 calc R U . . .
C5 C -0.1862(6) 0.0384(3) 0.49655(18) 0.0464(9) Uani 1 1 d . . . . .
C6 C -0.1156(5) 0.1299(3) 0.45476(18) 0.0476(10) Uani 1 1 d . . . . .
C7 C -0.0806(6) -0.0606(3) 0.4982(2) 0.0577(11) Uani 1 1 d . . . . .
C8 C -0.6119(7) -0.0334(4) 0.6118(2) 0.0897(15) Uani 1 1 d . . . . .
H8A H -0.6945 -0.0966 0.6019 0.135 Uiso 1 1 calc R U . . .
H8B H -0.6784 0.0351 0.6003 0.135 Uiso 1 1 calc R U . . .
H8C H -0.5807 -0.0331 0.6592 0.135 Uiso 1 1 calc R U . . .
C9 C 0.1460(6) 0.1821(3) 0.37413(17) 0.0467(9) Uani 1 1 d . . . . .
C10 C 0.0439(6) 0.2192(4) 0.3188(2) 0.0626(11) Uani 1 1 d . . . . .
H10 H -0.0848 0.1970 0.3123 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1334(6) 0.2898(4) 0.2727(2) 0.0638(11) Uani 1 1 d . . . . .
H11 H 0.0637 0.3139 0.2350 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3238(5) 0.3254(3) 0.28104(18) 0.0497(10) Uani 1 1 d . . . . .
C13 C 0.4213(6) 0.2865(3) 0.33766(19) 0.0539(10) Uani 1 1 d . . . . .
H13 H 0.5495 0.3090 0.3447 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3348(5) 0.2155(3) 0.38404(19) 0.0522(10) Uani 1 1 d . . . . .
H14 H 0.4041 0.1907 0.4216 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4206(6) 0.4043(4) 0.2303(2) 0.0637(11) Uani 1 1 d . . . . .
C16 C 0.3188(13) 0.4128(9) 0.1654(3) 0.133(4) Uani 0.790(8) 1 d . . P A 1
H16A H 0.3864 0.4649 0.1366 0.200 Uiso 0.790(8) 1 calc R U P A 1
H16B H 0.1881 0.4389 0.1728 0.200 Uiso 0.790(8) 1 calc R U P A 1
H16C H 0.3152 0.3401 0.1441 0.200 Uiso 0.790(8) 1 calc R U P A 1
C17 C 0.4297(14) 0.5222(6) 0.2644(4) 0.118(3) Uani 0.790(8) 1 d . . P A 1
H17A H 0.5007 0.5732 0.2359 0.178 Uiso 0.790(8) 1 calc R U P A 1
H17B H 0.4944 0.5160 0.3074 0.178 Uiso 0.790(8) 1 calc R U P A 1
H17C H 0.2998 0.5501 0.2711 0.178 Uiso 0.790(8) 1 calc R U P A 1
C18 C 0.6315(9) 0.3694(8) 0.2192(4) 0.116(4) Uani 0.790(8) 1 d . . P A 1
H18A H 0.6353 0.2950 0.2002 0.173 Uiso 0.790(8) 1 calc R U P A 1
H18B H 0.6993 0.3698 0.2616 0.173 Uiso 0.790(8) 1 calc R U P A 1
H18C H 0.6929 0.4213 0.1886 0.173 Uiso 0.790(8) 1 calc R U P A 1
C16A C 0.277(3) 0.504(2) 0.2148(13) 0.074(8) Uani 0.210(8) 1 d . U P A 2
H16D H 0.2313 0.5360 0.2566 0.111 Uiso 0.210(8) 1 calc R U P A 2
H16E H 0.1677 0.4767 0.1893 0.111 Uiso 0.210(8) 1 calc R U P A 2
H16F H 0.3436 0.5610 0.1892 0.111 Uiso 0.210(8) 1 calc R U P A 2
C17A C 0.460(5) 0.331(3) 0.1621(14) 0.110(10) Uani 0.210(8) 1 d . U P A 2
H17D H 0.5158 0.3793 0.1280 0.164 Uiso 0.210(8) 1 calc R U P A 2
H17E H 0.3389 0.3011 0.1459 0.164 Uiso 0.210(8) 1 calc R U P A 2
H17F H 0.5483 0.2710 0.1720 0.164 Uiso 0.210(8) 1 calc R U P A 2
C18A C 0.603(4) 0.459(3) 0.2508(13) 0.086(9) Uani 0.210(8) 1 d . U P A 2
H18D H 0.5964 0.4776 0.2981 0.128 Uiso 0.210(8) 1 calc R U P A 2
H18E H 0.6206 0.5268 0.2250 0.128 Uiso 0.210(8) 1 calc R U P A 2
H18F H 0.7102 0.4091 0.2429 0.128 Uiso 0.210(8) 1 calc R U P A 2
N1 N 0.0563(4) 0.1043(2) 0.42105(15) 0.0506(9) Uani 1 1 d . . . . .
N2 N 0.1599(5) 0.0048(3) 0.42615(18) 0.0703(10) Uani 1 1 d . . . . .
N3 N 0.0944(6) -0.0740(3) 0.4633(2) 0.0736(11) Uani 1 1 d . . . . .
O1 O -0.1943(4) 0.2217(2) 0.44807(13) 0.0588(8) Uani 1 1 d . . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C7 119.0(4)
C2 C1 H1 120.5
C7 C1 H1 120.5
C1 C2 C3 121.9(4)
C1 C2 H2 119.0
C3 C2 H2 119.0
C4 C3 C2 118.5(4)
C4 C3 C8 121.3(4)
C2 C3 C8 120.2(4)
C3 C4 C5 121.1(4)
C3 C4 H4 119.5
C5 C4 H4 119.5
C7 C5 C4 119.5(4)
C7 C5 C6 118.5(3)
C4 C5 C6 122.0(3)
O1 C6 N1 121.2(3)
O1 C6 C5 125.6(3)
N1 C6 C5 113.2(3)
C5 C7 N3 122.5(4)
C5 C7 C1 120.0(4)
N3 C7 C1 117.5(4)
C3 C8 H8A 109.5
C3 C8 H8B 109.5
H8A C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 C10 120.2(3)
C14 C9 N1 119.7(3)
C10 C9 N1 120.0(3)
C9 C10 C11 119.6(4)
C9 C10 H10 120.2
C11 C10 H10 120.2
C10 C11 C12 121.7(4)
C10 C11 H11 119.1
C12 C11 H11 119.1
C13 C12 C11 116.8(3)
C13 C12 C15 121.8(3)
C11 C12 C15 121.4(3)
C14 C13 C12 122.3(4)
C14 C13 H13 118.8
C12 C13 H13 118.8
C9 C14 C13 119.3(4)
C9 C14 H14 120.4
C13 C14 H14 120.4
C16 C15 C18 110.2(6)
C16 C15 C12 114.3(4)
C18A C15 C12 117.5(11)
C18 C15 C12 110.0(4)
C16 C15 C17 109.7(6)
C18 C15 C17 105.7(6)
C12 C15 C17 106.5(4)
C18A C15 C16A 104.6(15)
C12 C15 C16A 108.5(9)
C18A C15 C17A 109.0(16)
C12 C15 C17A 107.0(11)
C16A C15 C17A 110.2(15)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C15 C16A H16D 109.5
C15 C16A H16E 109.5
H16D C16A H16E 109.5
C15 C16A H16F 109.5
H16D C16A H16F 109.5
H16E C16A H16F 109.5
C15 C17A H17D 109.5
C15 C17A H17E 109.5
H17D C17A H17E 109.5
C15 C17A H17F 109.5
H17D C17A H17F 109.5
H17E C17A H17F 109.5
C15 C18A H18D 109.5
C15 C18A H18E 109.5
H18D C18A H18E 109.5
C15 C18A H18F 109.5
H18D C18A H18F 109.5
H18E C18A H18F 109.5
N2 N1 C6 126.0(3)
N2 N1 C9 112.0(3)
C6 N1 C9 122.0(3)
N3 N2 N1 119.3(3)
N2 N3 C7 120.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.367(6)
C1 C7 1.401(5)
C1 H1 0.9300
C2 C3 1.390(6)
C2 H2 0.9300
C3 C4 1.372(5)
C3 C8 1.510(6)
C4 C5 1.394(5)
C4 H4 0.9300
C5 C7 1.381(5)
C5 C6 1.448(5)
C6 O1 1.224(4)
C6 N1 1.387(5)
C7 N3 1.393(5)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C14 1.369(5)
C9 C10 1.372(5)
C9 N1 1.446(4)
C10 C11 1.381(5)
C10 H10 0.9300
C11 C12 1.383(5)
C11 H11 0.9300
C12 C13 1.383(5)
C12 C15 1.525(5)
C13 C14 1.379(5)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.464(7)
C15 C18A 1.47(2)
C15 C18 1.520(8)
C15 C17 1.556(8)
C15 C16A 1.57(2)
C15 C17A 1.62(3)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C16A H16D 0.9600
C16A H16E 0.9600
C16A H16F 0.9600
C17A H17D 0.9600
C17A H17E 0.9600
C17A H17F 0.9600
C18A H18D 0.9600
C18A H18E 0.9600
C18A H18F 0.9600
N1 N2 1.382(4)
N2 N3 1.272(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
C7 C1 C2 C3 -0.4(7)
C1 C2 C3 C4 0.7(6)
C1 C2 C3 C8 -178.8(4)
C2 C3 C4 C5 -0.3(6)
C8 C3 C4 C5 179.1(4)
C3 C4 C5 C7 -0.3(5)
C3 C4 C5 C6 178.0(3)
C7 C5 C6 O1 179.5(4)
C4 C5 C6 O1 1.2(6)
C7 C5 C6 N1 -0.3(5)
C4 C5 C6 N1 -178.6(3)
C4 C5 C7 N3 -179.2(4)
C6 C5 C7 N3 2.5(6)
C4 C5 C7 C1 0.6(6)
C6 C5 C7 C1 -177.7(4)
C2 C1 C7 C5 -0.3(6)
C2 C1 C7 N3 179.5(4)
C14 C9 C10 C11 0.6(6)
N1 C9 C10 C11 -177.3(4)
C9 C10 C11 C12 -0.7(6)
C10 C11 C12 C13 0.4(6)
C10 C11 C12 C15 -179.3(4)
C11 C12 C13 C14 0.0(6)
C15 C12 C13 C14 179.7(4)
C10 C9 C14 C13 -0.2(6)
N1 C9 C14 C13 177.7(3)
C12 C13 C14 C9 -0.1(6)
C13 C12 C15 C16 164.3(6)
C11 C12 C15 C16 -16.0(7)
C13 C12 C15 C18A -14.2(15)
C11 C12 C15 C18A 165.5(15)
C13 C12 C15 C18 39.7(7)
C11 C12 C15 C18 -140.6(6)
C13 C12 C15 C17 -74.3(6)
C11 C12 C15 C17 105.4(5)
C13 C12 C15 C16A -132.5(11)
C11 C12 C15 C16A 47.2(12)
C13 C12 C15 C17A 108.7(14)
C11 C12 C15 C17A -71.6(14)
O1 C6 N1 N2 178.3(4)
C5 C6 N1 N2 -1.9(5)
O1 C6 N1 C9 -3.0(5)
C5 C6 N1 C9 176.9(3)
C14 C9 N1 N2 -57.4(4)
C10 C9 N1 N2 120.5(4)
C14 C9 N1 C6 123.7(4)
C10 C9 N1 C6 -58.4(5)
C6 N1 N2 N3 1.9(6)
C9 N1 N2 N3 -177.0(3)
N1 N2 N3 C7 0.4(6)
C5 C7 N3 N2 -2.6(6)
C1 C7 N3 N2 177.6(4)
