#------------------------------------------------------------------------------
#$Date: 2020-07-07 02:20:15 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254034 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038551.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_4038551
loop_
_publ_author_name
'Dhiman, Ankit Kumar'
'Thakur, Ankita'
'Kumar, Inder'
'Kumar, Rakesh'
'Sharma, Upendra'
_publ_section_title
;
 Co(III)-Catalyzed C-H Amidation of Nitrogen Containing Heterocycles with
 Dioxazolones under Mild Condition.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01237
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.400(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1128(9)
_cell_length_b                   9.3254(11)
_cell_length_c                   17.1572(18)
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.4300
_cell_measurement_theta_min      5.2330
_cell_volume                     1276.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -49.00   1.00   1.00    1.00    --   25.69 -57.00-180.00   50
  2  ω      4.00  75.00   1.00    1.00    --   25.69 -99.00 -60.00   71
  3  ω      4.00  63.00   1.00    1.00    --   25.69 -57.00-180.00   59
  4  ω     31.00 124.00   1.00    8.00    --   66.85  63.00 -60.00   93
  5  ω    100.00 143.00   1.00    8.00    --   66.85 111.00-120.00   43
  6  ω     -6.00  19.00   1.00    8.00    --   66.85 -91.00 -90.00   25
  7  ω    122.00 148.00   1.00    8.00    --   66.85 178.00   0.00   26
  8  ω     45.00 150.00   1.00    8.00    --   66.85  77.00 150.00  105
  9  ω     47.00 103.00   1.00    8.00    --   66.85 -91.00 -90.00   56
 10  ω     76.00 103.00   1.00   30.00    --  108.00-104.00 -60.00   27
 11  ω     24.00  64.00   1.00   30.00    --  108.00-104.00 -60.00   40
 12  ω     32.00 103.00   1.00   30.00    --  108.00-104.00-180.00   71
 13  ω     42.00  80.00   1.00   30.00    --  108.00 -43.00  60.00   38
 14  ω     25.00  82.00   1.00   30.00    --  108.00 -32.00-180.00   57
 15  ω    111.00 175.00   1.00   30.00    --  108.00 104.00 120.00   64
 16  ω     74.00 104.00   1.00   30.00    --  108.00-104.00  90.00   30
 17  ω     24.00  58.00   1.00   30.00    --  108.00-104.00  90.00   34
 18  ω    144.00 173.00   1.00   30.00    --  108.00 -32.00-180.00   29
 19  ω     86.00 118.00   1.00   30.00    --  108.00 -32.00-180.00   32
 20  ω     94.00 144.00   1.00   30.00    --  108.00 -43.00  60.00   50
 21  ω     25.00  64.00   1.00   30.00    --  108.00-104.00 120.00   39
 22  ω     75.00 103.00   1.00   30.00    --  108.00-104.00   0.00   28
 23  ω    117.00 176.00   1.00   30.00    --  108.00 104.00  90.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1915883000
_diffrn_orient_matrix_UB_12      -0.0091723000
_diffrn_orient_matrix_UB_13      -0.0268452000
_diffrn_orient_matrix_UB_21      0.0070004000
_diffrn_orient_matrix_UB_22      -0.1630108000
_diffrn_orient_matrix_UB_23      0.0148585000
_diffrn_orient_matrix_UB_31      -0.0240655000
_diffrn_orient_matrix_UB_32      0.0253815000
_diffrn_orient_matrix_UB_33      0.0858835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3874
_diffrn_reflns_theta_full        66.84
_diffrn_reflns_theta_max         66.84
_diffrn_reflns_theta_min         5.24
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Square
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+0.1128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                1775
_reflns_number_total             2204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c01237_si_003.cif
_cod_data_source_block           usanb3_rt_cu
_cod_original_cell_volume        1276.7(2)
_cod_database_code               4038551
_chemical_oxdiff_formula         'C64 H48 N8 O8'
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C5(H5), C11(H11), C15(H15), C4(H4), C13(H13), C10(H10),
 C14(H14), C1(H1A), C3(H3), C2(H2)
;
_olex2_date_sample_data_collection 2019-12-10
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.803
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.49587(16) 0.38469(16) 0.58705(8) 0.0573(4) Uani 1 d . . .
H1 H 0.3914 0.3747 0.5670 0.069 Uiso 1 calc . . R
O2 O 0.25685(15) 0.26910(19) 0.49135(9) 0.0819(5) Uani 1 d . . .
N2 N 0.36800(17) 0.20180(16) 0.45706(8) 0.0581(4) Uani 1 d . . .
O1 O 0.67159(18) 0.5066(2) 0.68195(10) 0.0963(6) Uani 1 d . . .
C16 C 0.53942(18) 0.21095(17) 0.48750(9) 0.0501(4) Uani 1 d . . .
C8 C 0.60662(19) 0.29945(18) 0.55331(9) 0.0517(4) Uani 1 d . . .
C12 C 0.6484(2) 0.12691(18) 0.45000(9) 0.0557(4) Uani 1 d . . .
C6 C 0.3806(2) 0.55496(18) 0.66814(9) 0.0554(4) Uani 1 d . . .
C7 C 0.5308(2) 0.48037(19) 0.64669(10) 0.0579(4) Uani 1 d . . .
C9 C 0.7781(2) 0.2983(2) 0.58027(11) 0.0633(4) Uani 1 d . . .
H9 H 0.8237 0.3548 0.6235 0.076 Uiso 1 calc . . R
C5 C 0.2189(2) 0.54434(19) 0.62489(10) 0.0614(4) Uani 1 d . . .
H5 H 0.1987 0.4888 0.5791 0.074 Uiso 1 calc . . R
C11 C 0.8223(2) 0.1310(2) 0.48020(11) 0.0669(5) Uani 1 d . . .
H11 H 0.8950 0.0763 0.4562 0.080 Uiso 1 calc . . R
C15 C 0.3106(2) 0.1234(2) 0.39305(11) 0.0670(5) Uani 1 d . . .
H15 H 0.1960 0.1219 0.3735 0.080 Uiso 1 calc . . R
C4 C 0.0875(3) 0.6159(2) 0.64943(12) 0.0711(5) Uani 1 d . . .
H4 H -0.0206 0.6076 0.6205 0.085 Uiso 1 calc . . R
C13 C 0.5827(3) 0.0441(2) 0.38321(11) 0.0669(5) Uani 1 d . . .
H13 H 0.6540 -0.0108 0.3585 0.080 Uiso 1 calc . . R
C10 C 0.8842(2) 0.2132(2) 0.54343(12) 0.0693(5) Uani 1 d . . .
H10 H 0.9989 0.2135 0.5629 0.083 Uiso 1 calc . . R
C14 C 0.4161(3) 0.0441(2) 0.35469(11) 0.0722(5) Uani 1 d . . .
H14 H 0.3727 -0.0088 0.3097 0.087 Uiso 1 calc . . R
C1 C 0.4077(3) 0.6400(2) 0.73553(11) 0.0706(5) Uani 1 d . . .
H1A H 0.5153 0.6488 0.7650 0.085 Uiso 1 calc . . R
C3 C 0.1174(3) 0.6994(2) 0.71707(13) 0.0781(6) Uani 1 d . . .
H3 H 0.0295 0.7472 0.7339 0.094 Uiso 1 calc . . R
C2 C 0.2768(3) 0.7115(3) 0.75916(13) 0.0835(6) Uani 1 d . . .
H2 H 0.2969 0.7686 0.8043 0.100 Uiso 1 calc . . R
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 1 0 0.0444
-5 -1 0 0.0444
1 0 -11 0.0563
0 0 11 0.0581
-4 2 -3 0.0628
-5 0 6 0.0469
3 0 -10 0.0561
-5 -3 0 0.0656
-1 -4 8 0.0951
1 -4 8 0.0850
3 -2 8 0.0577
3 1 8 0.0410
4 3 1 0.0625
0 6 -1 0.1082
-2 0 -9 0.0500
-4 0 -4 0.0374
-1 -6 3 0.1119
5 0 3 0.0331
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
C8 N1 H1 115.6 . . ?
C7 N1 H1 115.6 . . ?
C7 N1 C8 128.80(14) . . ?
O2 N2 C16 121.20(14) . . ?
O2 N2 C15 117.60(14) . . ?
C15 N2 C16 121.20(15) . . ?
N2 C16 C8 122.97(14) . . ?
N2 C16 C12 117.15(15) . . ?
C12 C16 C8 119.88(14) . . ?
N1 C8 C16 118.28(13) . . ?
C9 C8 N1 123.18(16) . . ?
C9 C8 C16 118.53(15) . . ?
C11 C12 C16 118.77(16) . . ?
C13 C12 C16 119.82(16) . . ?
C13 C12 C11 121.39(16) . . ?
C5 C6 C7 124.36(15) . . ?
C1 C6 C7 117.02(16) . . ?
C1 C6 C5 118.62(17) . . ?
N1 C7 C6 115.02(14) . . ?
O1 C7 N1 124.02(17) . . ?
O1 C7 C6 120.96(16) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.03(17) . . ?
C10 C9 H9 119.5 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.49(18) . . ?
C4 C5 H5 119.8 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.82(17) . . ?
C10 C11 H11 119.6 . . ?
N2 C15 H15 118.9 . . ?
N2 C15 C14 122.13(17) . . ?
C14 C15 H15 118.9 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.20(17) . . ?
C14 C13 H13 119.9 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.95(16) . . ?
C11 C10 H10 119.5 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.42(18) . . ?
C13 C14 H14 120.3 . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 C6 120.51(19) . . ?
C2 C1 H1A 119.7 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.73(19) . . ?
C2 C3 H3 120.1 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
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 H1 0.8600 . ?
N1 C8 1.401(2) . ?
N1 C7 1.349(2) . ?
O2 N2 1.3208(19) . ?
N2 C16 1.397(2) . ?
N2 C15 1.332(2) . ?
O1 C7 1.217(2) . ?
C16 C8 1.425(2) . ?
C16 C12 1.420(2) . ?
C8 C9 1.385(2) . ?
C12 C11 1.413(3) . ?
C12 C13 1.405(3) . ?
C6 C7 1.505(2) . ?
C6 C5 1.389(2) . ?
C6 C1 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.349(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.352(3) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.367(4) . ?
C2 H2 0.9300 . ?
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
N1 H1 O2 0.86 1.83 2.5433(18) 139.7 .
C9 H9 O1 0.93 2.23 2.847(3) 123.1 .
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
N1 C8 C9 C10 -178.65(17) . . . . ?
O2 N2 C16 C8 -4.3(2) . . . . ?
O2 N2 C16 C12 175.65(16) . . . . ?
O2 N2 C15 C14 -177.31(19) . . . . ?
N2 C16 C8 N1 -2.3(2) . . . . ?
N2 C16 C8 C9 178.39(15) . . . . ?
N2 C16 C12 C11 -178.66(15) . . . . ?
N2 C16 C12 C13 2.6(2) . . . . ?
N2 C15 C14 C13 0.8(3) . . . . ?
C16 N2 C15 C14 1.8(3) . . . . ?
C16 C8 C9 C10 0.6(3) . . . . ?
C16 C12 C11 C10 -0.1(3) . . . . ?
C16 C12 C13 C14 -0.1(3) . . . . ?
C8 N1 C7 O1 -0.6(3) . . . . ?
C8 N1 C7 C6 179.62(15) . . . . ?
C8 C16 C12 C11 1.3(2) . . . . ?
C8 C16 C12 C13 -177.48(15) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C12 C16 C8 N1 177.78(14) . . . . ?
C12 C16 C8 C9 -1.5(2) . . . . ?
C12 C11 C10 C9 -0.8(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 N1 C8 C16 -176.85(16) . . . . ?
C7 N1 C8 C9 2.4(3) . . . . ?
C7 C6 C5 C4 179.41(17) . . . . ?
C7 C6 C1 C2 -179.85(19) . . . . ?
C5 C6 C7 N1 -8.5(2) . . . . ?
C5 C6 C7 O1 171.77(19) . . . . ?
C5 C6 C1 C2 0.4(3) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C11 C12 C13 C14 -178.85(18) . . . . ?
C15 N2 C16 C8 176.64(16) . . . . ?
C15 N2 C16 C12 -3.4(2) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?
C13 C12 C11 C10 178.65(18) . . . . ?
C1 C6 C7 N1 171.83(16) . . . . ?
C1 C6 C7 O1 -7.9(3) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0010 1.0022 -0.0066 -0.9671 -0.1285 -0.0955
-5.0010 -1.0022 0.0066 0.9671 0.1285 0.0955
0.9968 0.0034 -11.0022 0.1044 -0.1571 -0.9688
0.0036 -0.0029 11.0011 -0.2960 0.1640 0.9447
-4.0042 1.9970 -2.9979 0.8293 -0.3981 -0.1104
-4.9999 -0.0045 6.0062 0.7967 0.0550 0.6360
2.9979 0.0044 -10.0043 -0.3058 -0.1284 -0.9312
-4.9992 -3.0007 0.0086 0.9851 0.4543 0.0449
-0.9943 -3.9997 8.0060 0.0123 0.7640 0.6100
1.0065 -3.9986 8.0037 -0.3710 0.7778 0.5617
3.0055 -1.9989 7.9995 -0.7722 0.4657 0.5640
3.0028 0.9989 7.9964 -0.7991 -0.0230 0.6398
3.9992 2.9999 0.9926 -0.8204 -0.4463 0.0651
-0.0056 5.9958 -1.0062 -0.0269 -0.9924 0.0659
-2.0037 0.0012 -8.9986 0.6254 -0.1479 -0.7246
-4.0028 -0.0013 -3.9959 0.8742 -0.0872 -0.2469
-0.9942 -5.9970 3.0075 0.1647 1.0153 0.1300
5.0028 0.0021 2.9947 -1.0389 0.0792 0.1369
