#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:16:43 +0300 (Fri, 05 May 2023) $
#$Revision: 283450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159085.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_7159085
loop_
_publ_author_name
'Padmavathi, Rayavarapu'
'Babu, Srinivasarao Arulananda'
_publ_section_title
;
 Pd(II)-catalyzed selective β-C-H functionalization of azobenzene
 carboxamides.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2689
_journal_page_last               2694
_journal_paper_doi               10.1039/d2ob02261c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33
_chemical_name_systematic        C20H14N2O3
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-13 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.588(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6384(9)
_cell_length_b                   19.8168(19)
_cell_length_c                   9.4404(11)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.3850
_cell_measurement_theta_min      2.9830
_cell_volume                     1593.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00 114.00   0.50   20.00    --   29.89  54.00-120.00  362
  2  ω     79.00 104.00   0.50   20.00    --   29.89  54.00  30.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047301000
_diffrn_orient_matrix_UB_12      0.0080228000
_diffrn_orient_matrix_UB_13      0.0724192000
_diffrn_orient_matrix_UB_21      0.0419391000
_diffrn_orient_matrix_UB_22      -0.0298990000
_diffrn_orient_matrix_UB_23      0.0229929000
_diffrn_orient_matrix_UB_31      0.0717388000
_diffrn_orient_matrix_UB_32      0.0179729000
_diffrn_orient_matrix_UB_33      0.0059658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5199
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.603
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0507
_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)+(0.0767P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1782
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02261c2.cif
_cod_data_source_block           rp1338
_cod_depositor_comments          'Adding full bibliography for 7159085.cif.'
_cod_database_code               7159085
_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_max   0.972
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C7(H7), C4(H4), C13(H13), C14(H14), C3(H3), C16(H16),
 C17(H17), C19(H19), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_original_sample_id 'rp 1338'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.943
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O3 O 0.73864(17) 0.53246(7) 0.63711(15) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.81753(19) 0.59596(8) 0.16726(18) 0.0770(5) Uani 1 1 d . . . . .
O2 O 0.7178(2) 0.50267(9) 0.85725(17) 0.0808(6) Uani 1 1 d . . . . .
N2 N 0.0647(2) 0.66227(9) 0.6743(2) 0.0631(5) Uani 1 1 d . . . . .
N3 N -0.0087(2) 0.65941(9) 0.7757(2) 0.0619(5) Uani 1 1 d . . . . .
C5 C 0.5353(2) 0.59545(9) 0.4851(2) 0.0488(5) Uani 1 1 d . . . . .
C8 C 0.4428(2) 0.59606(9) 0.5999(2) 0.0493(5) Uani 1 1 d . . . . .
C15 C -0.1553(2) 0.69485(10) 0.7510(2) 0.0537(5) Uani 1 1 d . . . . .
C9 C 0.5044(2) 0.56562(10) 0.7308(2) 0.0515(5) Uani 1 1 d . . . . .
C6 C 0.6823(2) 0.56445(9) 0.5086(2) 0.0512(5) Uani 1 1 d . . . . .
C11 C 0.2950(2) 0.62696(10) 0.5886(2) 0.0546(5) Uani 1 1 d . . . . .
H11 H 0.2507 0.6474 0.5027 0.065 Uiso 1 1 calc R U . . .
C10 C 0.6573(3) 0.53167(11) 0.7503(2) 0.0577(6) Uani 1 1 d . . . . .
C20 C -0.2372(3) 0.69409(11) 0.8636(2) 0.0624(6) Uani 1 1 d . . . . .
H20 H -0.1976 0.6706 0.9472 0.075 Uiso 1 1 calc R U . . .
C12 C 0.2150(2) 0.62741(10) 0.7029(2) 0.0559(6) Uani 1 1 d . . . . .
C7 C 0.7804(2) 0.56305(10) 0.4066(2) 0.0565(6) Uani 1 1 d . . . . .
H7 H 0.8772 0.5415 0.4258 0.068 Uiso 1 1 calc R U . . .
C2 C 0.7324(3) 0.59407(10) 0.2764(2) 0.0592(6) Uani 1 1 d . . . . .
C4 C 0.4921(3) 0.62663(11) 0.3513(2) 0.0602(6) Uani 1 1 d . . . . .
H4 H 0.3954 0.6483 0.3312 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2780(3) 0.59808(11) 0.8336(3) 0.0646(6) Uani 1 1 d . . . . .
H13 H 0.2238 0.5992 0.9107 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4222(3) 0.56735(11) 0.8462(2) 0.0637(6) Uani 1 1 d . . . . .
H14 H 0.4657 0.5474 0.9329 0.076 Uiso 1 1 calc R U . . .
C3 C 0.5872(3) 0.62632(11) 0.2492(3) 0.0650(6) Uani 1 1 d . . . . .
H3 H 0.5549 0.6477 0.1615 0.078 Uiso 1 1 calc R U . . .
C16 C -0.2151(3) 0.72893(11) 0.6254(2) 0.0642(6) Uani 1 1 d . . . . .
H16 H -0.1608 0.7290 0.5482 0.077 Uiso 1 1 calc R U . . .
C17 C -0.3557(3) 0.76266(12) 0.6162(3) 0.0729(7) Uani 1 1 d . . . . .
H17 H -0.3961 0.7861 0.5329 0.087 Uiso 1 1 calc R U . . .
C19 C -0.3777(3) 0.72794(12) 0.8534(3) 0.0706(7) Uani 1 1 d . . . . .
H19 H -0.4325 0.7277 0.9303 0.085 Uiso 1 1 calc R U . . .
C18 C -0.4369(3) 0.76184(12) 0.7303(3) 0.0706(7) Uani 1 1 d . . . . .
H18 H -0.5322 0.7844 0.7233 0.085 Uiso 1 1 calc R U . . .
C1 C 0.9626(3) 0.55985(14) 0.1830(3) 0.0834(8) Uani 1 1 d . . . . .
H1A H 1.0066 0.5640 0.0964 0.125 Uiso 1 1 calc R U . . .
H1B H 0.9442 0.5131 0.2009 0.125 Uiso 1 1 calc R U . . .
H1C H 1.0345 0.5782 0.2621 0.125 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
C10 O3 C6 122.43(16) . . ?
C2 O1 C1 118.82(19) . . ?
N3 N2 C12 113.04(19) . . ?
N2 N3 C15 113.93(18) . . ?
C6 C5 C8 119.03(18) . . ?
C6 C5 C4 115.92(19) . . ?
C4 C5 C8 124.98(18) . . ?
C9 C8 C5 118.71(18) . . ?
C9 C8 C11 117.62(19) . . ?
C11 C8 C5 123.65(18) . . ?
C20 C15 N3 115.10(19) . . ?
C20 C15 C16 120.1(2) . . ?
C16 C15 N3 124.8(2) . . ?
C8 C9 C10 120.78(19) . . ?
C14 C9 C8 120.67(19) . . ?
C14 C9 C10 118.55(19) . . ?
O3 C6 C5 121.32(18) . . ?
O3 C6 C7 115.70(18) . . ?
C7 C6 C5 122.98(19) . . ?
C8 C11 H11 119.6 . . ?
C12 C11 C8 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
O3 C10 C9 117.66(18) . . ?
O2 C10 O3 116.84(19) . . ?
O2 C10 C9 125.5(2) . . ?
C15 C20 H20 119.9 . . ?
C15 C20 C19 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C11 C12 N2 114.0(2) . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 N2 124.7(2) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 H7 120.5 . . ?
O1 C2 C7 124.6(2) . . ?
O1 C2 C3 115.5(2) . . ?
C7 C2 C3 119.9(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
O3 C6 1.383(2) . ?
O3 C10 1.373(2) . ?
O1 C2 1.362(2) . ?
O1 C1 1.429(3) . ?
O2 C10 1.203(2) . ?
N2 N3 1.235(2) . ?
N2 C12 1.455(3) . ?
N3 C15 1.433(3) . ?
C5 C8 1.450(3) . ?
C5 C6 1.394(3) . ?
C5 C4 1.400(3) . ?
C8 C9 1.398(3) . ?
C8 C11 1.403(3) . ?
C15 C20 1.372(3) . ?
C15 C16 1.388(3) . ?
C9 C10 1.466(3) . ?
C9 C14 1.397(3) . ?
C6 C7 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.377(3) . ?
C12 C13 1.390(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.375(3) . ?
C2 C3 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.367(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.366(3) . ?
C18 H18 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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
O3 C6 C7 C2 -179.74(17) . . . . ?
O1 C2 C3 C4 179.3(2) . . . . ?
N2 N3 C15 C20 -178.23(19) . . . . ?
N2 N3 C15 C16 1.1(3) . . . . ?
N2 C12 C13 C14 -179.29(19) . . . . ?
N3 N2 C12 C11 176.79(18) . . . . ?
N3 N2 C12 C13 -4.8(3) . . . . ?
N3 C15 C20 C19 178.36(19) . . . . ?
N3 C15 C16 C17 -178.25(19) . . . . ?
C5 C8 C9 C10 -2.1(3) . . . . ?
C5 C8 C9 C14 177.44(19) . . . . ?
C5 C8 C11 C12 -178.17(19) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C8 C5 C6 O3 2.2(3) . . . . ?
C8 C5 C6 C7 -178.21(18) . . . . ?
C8 C5 C4 C3 177.6(2) . . . . ?
C8 C9 C10 O3 1.6(3) . . . . ?
C8 C9 C10 O2 -178.0(2) . . . . ?
C8 C9 C14 C13 0.9(3) . . . . ?
C8 C11 C12 N2 179.18(17) . . . . ?
C8 C11 C12 C13 0.7(3) . . . . ?
C15 C20 C19 C18 0.7(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C9 C8 C11 C12 0.4(3) . . . . ?
C6 O3 C10 O2 -179.58(18) . . . . ?
C6 O3 C10 C9 0.8(3) . . . . ?
C6 C5 C8 C9 0.2(3) . . . . ?
C6 C5 C8 C11 178.71(18) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C6 C7 C2 O1 -179.69(19) . . . . ?
C6 C7 C2 C3 0.1(3) . . . . ?
C11 C8 C9 C10 179.29(18) . . . . ?
C11 C8 C9 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C10 O3 C6 C5 -2.8(3) . . . . ?
C10 O3 C6 C7 177.66(18) . . . . ?
C10 C9 C14 C13 -179.6(2) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C20 C19 C18 C17 -0.4(3) . . . . ?
C12 N2 N3 C15 178.55(16) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C4 C5 C8 C9 -176.78(19) . . . . ?
C4 C5 C8 C11 1.8(3) . . . . ?
C4 C5 C6 O3 179.45(17) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C14 C9 C10 O3 -177.88(19) . . . . ?
C14 C9 C10 O2 2.5(3) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C1 O1 C2 C7 4.3(3) . . . . ?
C1 O1 C2 C3 -175.5(2) . . . . ?
