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#$Date: 2020-09-26 02:17:57 +0300 (Sat, 26 Sep 2020) $
#$Revision: 256779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038841.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_4038841
loop_
_publ_author_name
'Huang, Yange'
'Choy, Pui Ying'
'Wang, Junya'
'Tse, Man Kin'
'Sun, Raymond Wai-Yin'
'Chan, Albert Sun Chi'
'Kwong, Fuk Yee'
_publ_section_title
;
 Palladium-catalyzed Monoarylation of Arylhydrazines with Aryl Tosylates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01599
_journal_year                    2020
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.781(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.327(4)
_cell_length_b                   15.647(9)
_cell_length_c                   7.711(4)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     877.8(8)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15674
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_min         2.603
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       0.10(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0662
_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)+(0.0597P)²+0.4627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2249
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01599_si_005.cif
_cod_data_source_block           HYG18101
_cod_original_cell_volume        877.9(8)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4038841
_shelx_shelxl_version_number     2018/3
_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   0.968
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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
N1 N -0.3970(6) -0.6551(3) -0.6391(6) 0.0503(13) Uani 1 1 d . . . . .
N2 N -0.4100(6) -0.7428(4) -0.6320(7) 0.0588(14) Uani 1 1 d . . . . .
O1 O -0.9635(6) -0.3755(3) -0.5872(9) 0.098(2) Uani 1 1 d . . . . .
H1B H -1.041430 -0.413267 -0.601360 0.148 Uiso 1 1 calc R U . . .
O2 O -0.2618(5) -0.4985(3) -0.6328(7) 0.0756(16) Uani 1 1 d . . . . .
H2A H -0.189804 -0.458321 -0.617578 0.113 Uiso 1 1 calc R U . . .
C1 C -0.7904(8) -0.4104(5) -0.6005(9) 0.0594(17) Uani 1 1 d . . . . .
C2 C -0.6477(8) -0.3534(5) -0.6061(10) 0.069(2) Uani 1 1 d . . . . .
H2B H -0.669285 -0.294945 -0.602345 0.082 Uiso 1 1 calc R U . . .
C3 C -0.4715(8) -0.3840(5) -0.6174(9) 0.0621(18) Uani 1 1 d . . . . .
H3A H -0.375219 -0.345625 -0.622349 0.075 Uiso 1 1 calc R U . . .
C4 C -0.4385(7) -0.4697(5) -0.6214(8) 0.0526(16) Uani 1 1 d . . . . .
C5 C -0.5817(7) -0.5290(5) -0.6151(8) 0.0470(15) Uani 1 1 d . . . . .
C6 C -0.7601(8) -0.4957(5) -0.6043(8) 0.0526(16) Uani 1 1 d . . . . .
H6A H -0.857975 -0.533135 -0.599730 0.063 Uiso 1 1 calc R U . . .
C7 C -0.5541(6) -0.6199(4) -0.6191(7) 0.0476(16) Uani 1 1 d . . . . .
C8 C -0.7030(8) -0.6848(4) -0.6085(9) 0.0610(18) Uani 1 1 d . . . . .
H8A H -0.794913 -0.681352 -0.709658 0.073 Uiso 1 1 calc R U . . .
H8B H -0.762406 -0.676746 -0.503690 0.073 Uiso 1 1 calc R U . . .
C9 C -0.5998(7) -0.7713(4) -0.6036(8) 0.0566(16) Uani 1 1 d . . . . .
H9A H -0.651152 -0.806482 -0.702543 0.068 Uiso 1 1 calc R U . . .
C10 C -0.6062(7) -0.8205(4) -0.4362(8) 0.0509(15) Uani 1 1 d . . . . .
C11 C -0.7710(8) -0.8570(5) -0.4029(8) 0.0660(19) Uani 1 1 d . . . . .
H11A H -0.874135 -0.851396 -0.484863 0.079 Uiso 1 1 calc R U . . .
C12 C -0.7847(11) -0.9010(6) -0.2515(10) 0.084(3) Uani 1 1 d . . . . .
H12A H -0.896375 -0.925270 -0.232286 0.101 Uiso 1 1 calc R U . . .
C13 C -0.6353(12) -0.9096(6) -0.1279(10) 0.081(2) Uani 1 1 d . . . . .
H13A H -0.645526 -0.939308 -0.025059 0.097 Uiso 1 1 calc R U . . .
C14 C -0.4707(10) -0.8742(5) -0.1571(9) 0.077(2) Uani 1 1 d . . . . .
H14A H -0.368540 -0.880143 -0.074186 0.092 Uiso 1 1 calc R U . . .
C15 C -0.4559(8) -0.8293(5) -0.3104(9) 0.0651(19) Uani 1 1 d . . . . .
H15A H -0.344095 -0.804863 -0.328713 0.078 Uiso 1 1 calc R U . . .
C16 C -0.2895(7) -0.7958(4) -0.7101(8) 0.0501(15) Uani 1 1 d . . . . .
C17 C -0.2991(8) -0.8843(4) -0.6962(8) 0.0573(17) Uani 1 1 d . . . . .
H17A H -0.388529 -0.908351 -0.635257 0.069 Uiso 1 1 calc R U . . .
C18 C -0.1792(8) -0.9375(5) -0.7705(8) 0.0609(18) Uani 1 1 d . . . . .
H18A H -0.188047 -0.996475 -0.759598 0.073 Uiso 1 1 calc R U . . .
C19 C -0.0439(8) -0.9015(5) -0.8625(9) 0.0614(18) Uani 1 1 d . . . . .
H19A H 0.038464 -0.936286 -0.912595 0.074 Uiso 1 1 calc R U . . .
C20 C -0.0348(8) -0.8143(5) -0.8775(9) 0.0586(16) Uani 1 1 d . . . . .
H20A H 0.054067 -0.790697 -0.939684 0.070 Uiso 1 1 calc R U . . .
C21 C -0.1535(7) -0.7604(5) -0.8033(8) 0.0549(16) Uani 1 1 d . . . . .
H21A H -0.143606 -0.701476 -0.814823 0.066 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 110.5(5) . . ?
N1 N2 C16 121.6(4) . . ?
N1 N2 C9 111.8(4) . . ?
C16 N2 C9 122.0(5) . . ?
C1 O1 H1B 109.5 . . ?
C4 O2 H2A 109.5 . . ?
C6 C1 C2 120.7(6) . . ?
C6 C1 O1 122.7(6) . . ?
C2 C1 O1 116.6(6) . . ?
C1 C2 C3 119.6(7) . . ?
C1 C2 H2B 120.2 . . ?
C3 C2 H2B 120.2 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 O2 119.4(6) . . ?
C3 C4 C5 120.9(5) . . ?
O2 C4 C5 119.8(5) . . ?
C4 C5 C6 117.2(6) . . ?
C4 C5 C7 123.0(5) . . ?
C6 C5 C7 119.8(5) . . ?
C1 C6 C5 121.2(6) . . ?
C1 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
N1 C7 C5 123.4(6) . . ?
N1 C7 C8 112.3(6) . . ?
C5 C7 C8 124.3(5) . . ?
C7 C8 C9 103.7(5) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N2 C9 C10 113.6(5) . . ?
N2 C9 C8 101.3(5) . . ?
C10 C9 C8 113.8(5) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C15 C10 C11 117.8(6) . . ?
C15 C10 C9 123.2(5) . . ?
C11 C10 C9 119.0(5) . . ?
C12 C11 C10 121.2(7) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 120.6(7) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C13 C14 119.5(7) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C10 C15 C14 120.7(6) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 N2 121.1(5) . . ?
C17 C16 C21 118.4(5) . . ?
N2 C16 C21 120.5(6) . . ?
C18 C17 C16 121.8(6) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C19 119.3(7) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
C20 C19 C18 119.1(6) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C19 C20 C21 122.2(6) . . ?
C19 C20 H20A 118.9 . . ?
C21 C20 H20A 118.9 . . ?
C20 C21 C16 119.2(6) . . ?
C20 C21 H21A 120.4 . . ?
C16 C21 H21A 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.302(7) . ?
N1 N2 1.377(7) . ?
N2 C16 1.398(7) . ?
N2 C9 1.501(7) . ?
O1 C1 1.396(7) . ?
O1 H1B 0.8200 . ?
O2 C4 1.383(7) . ?
O2 H2A 0.8200 . ?
C1 C6 1.353(9) . ?
C1 C2 1.379(9) . ?
C2 C3 1.389(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.365(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.405(8) . ?
C5 C6 1.418(8) . ?
C5 C7 1.438(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.500(9) . ?
C8 C9 1.549(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.509(9) . ?
C9 H9A 0.9800 . ?
C10 C15 1.385(8) . ?
C10 C11 1.387(8) . ?
C11 C12 1.370(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(11) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.390(10) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.392(8) . ?
C16 C21 1.409(7) . ?
C17 C18 1.382(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.403(8) . ?
C18 H18A 0.9300 . ?
C19 C20 1.371(9) . ?
C19 H19A 0.9300 . ?
C20 C21 1.383(9) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
