#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:47:47 +0200 (Fri 05 de May de 2023) $
#$Revision: 283361 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/65/7246546.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_7246546
loop_
_publ_author_name
'Bhukta, Swadhapriya'
'Chatterjee, Rana'
'Dandela, Rambabu'
_publ_section_title
;
 Metal-free, 2-MeTHF mediated C(sp)--H functionalization of alkynes with
 anilines to access diaryl 1,2-diketones bearing lower E-factors
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3034
_journal_page_last               3039
_journal_paper_doi               10.1039/D3GC00267E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C14 H10 O2'
_chemical_formula_sum            'C14 H10 O2'
_chemical_formula_weight         210.22
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.415(1)
_cell_length_b                   8.415(1)
_cell_length_c                   13.689(2)
_cell_measurement_reflns_used    576
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      0.985
_cell_measurement_theta_min      0.982
_cell_volume                     839.48(19)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8825
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_min         2.795
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             330.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0494
_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)+(0.1000P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.2289
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                576
_reflns_number_total             1272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00267e2.cif
_cod_data_source_block           SB_N_0m_a
_cod_depositor_comments          'Adding full bibliography for 7246546.cif.'
_cod_original_cell_volume        839.5(2)
_cod_database_code               7246546
_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_res_file
;
TITL SB_N_0m_a.res in P3(2)21
    SB_N_0m_a.res
    created by SHELXL-2018/3 at 15:49:24 on 20-Jan-2023
CELL  0.71073   8.4152   8.4152  13.6891   90.000   90.000  120.000
ZERR   25.000   0.0010   0.0010   0.0020    0.000    0.000    0.000
LATT -1
SYMM -Y, X-Y, 2/3+Z
SYMM -X+Y, -X, 1/3+Z
SYMM Y, X, -Z
SYMM X-Y, -Y, 1/3-Z
SYMM -X, -X+Y, 2/3-Z
SFAC C  H  O
UNIT 25  25  25
REM Old TITL SB_N_0m in P3(2)21
REM SHELXT solution in P3(2)21: R1 0.195, Rweak 0.029, Alpha 0.008
REM <I/s>   0.876 for   10 systematic absences,  Orientation as input
REM Flack x= -1.584 ( 1.808 ) from   194 Parsons' quotients
REM Formula found by SHELXT:  C7 O
L.S. 10
ACTA
BOND
FMAP 2
PLAN 20
TEMP 0
WGHT    0.100000    0.771660
FVAR       2.23311
O1    3    0.741341   -0.310351    0.388322    11.00000    0.14756    0.10786 =
         0.12484   -0.03304   -0.03076    0.08140
C1    1    0.769318   -0.022446    0.424239    11.00000    0.06932    0.07681 =
         0.09109   -0.00323    0.00323    0.04004
C6    1    0.821188    0.115016    0.492734    11.00000    0.08920    0.08204 =
         0.09976   -0.00413    0.01044    0.04404
AFIX  43
H6    2    0.857312    0.101391    0.554913    11.00000   -1.20000
AFIX   0
C7    1    0.773886   -0.190101    0.447755    11.00000    0.07847    0.08339 =
         0.10144   -0.00984   -0.00341    0.04683
C2    1    0.715765   -0.000213    0.331779    11.00000    0.08968    0.10607 =
         0.10434   -0.00194   -0.00294    0.05740
AFIX  43
H2    2    0.680428   -0.092613    0.285399    11.00000   -1.20000
AFIX   0
C3    1    0.714902    0.158246    0.308686    11.00000    0.12470    0.12212 =
         0.13087    0.02720    0.01425    0.08204
AFIX  43
H3    2    0.679587    0.173219    0.246560    11.00000   -1.20000
AFIX   0
C4    1    0.765739    0.293648    0.376699    11.00000    0.13998    0.10237 =
         0.15543    0.03275    0.04176    0.08036
AFIX  43
H4    2    0.764134    0.400267    0.360763    11.00000   -1.20000
AFIX   0
C5    1    0.818968    0.273897    0.467995    11.00000    0.12044    0.08109 =
         0.13846    0.00333    0.03098    0.05111
AFIX  43
H5    2    0.853860    0.367211    0.513769    11.00000   -1.20000
AFIX   0
HKLF 4




REM  SB_N_0m_a.res in P3(2)21
REM wR2 = 0.228941, GooF = S = 0.77129, Restrained GooF = 0.77129 for all data
REM R1 = 0.049369 for 576 Fo > 4sig(Fo) and 0.133550 for all 1272 data
REM 73 parameters refined using 0 restraints

END

WGHT      0.0745      0.0404

REM Highest difference peak  0.107,  deepest hole -0.104,  1-sigma level  0.028
Q1    1   0.7639  0.3223  0.5798  11.00000  0.05    0.11
Q2    1   0.5788 -0.1789  0.4640  11.00000  0.05    0.10
Q3    1   0.5329 -0.0901  0.3936  11.00000  0.05    0.09
Q4    1   0.6143 -0.0669  0.4862  11.00000  0.05    0.09
Q5    1   0.5574 -0.1673  0.3224  11.00000  0.05    0.08
Q6    1   1.0131  0.4176  0.3966  11.00000  0.05    0.08
Q7    1   0.8119  0.4661  0.5900  11.00000  0.05    0.08
Q8    1   0.5542 -0.3230  0.4728  11.00000  0.05    0.08
Q9    1   0.9292  0.2497  0.2787  11.00000  0.05    0.08
Q10   1   0.6648  0.3119  0.5125  11.00000  0.05    0.08
Q11   1   0.8435 -0.3784  0.4619  11.00000  0.05    0.07
Q12   1   0.7792  0.4169  0.4940  11.00000  0.05    0.07
Q13   1   0.6382 -0.5247  0.4505  11.00000  0.05    0.07
Q14   1   0.7982  0.5377  0.4731  11.00000  0.05    0.07
Q15   1   0.9395  0.2590  0.3833  11.00000  0.05    0.07
Q16   1   0.7258  0.4638  0.4850  11.00000  0.05    0.07
Q17   1   0.6268  0.0000  0.1667  10.50000  0.05    0.07
Q18   1   0.7043 -0.0656  0.1646  11.00000  0.05    0.07
Q19   1   0.6776  0.3152  0.2609  11.00000  0.05    0.06
Q20   1   0.6303 -0.1055  0.3165  11.00000  0.05    0.06
;
_shelx_res_checksum              14612
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
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
O1 O 0.7413(7) -0.3104(7) 0.3883(3) 0.1190(17) Uani 1 1 d . . . . .
C1 C 0.7693(7) -0.0224(7) 0.4242(4) 0.0775(13) Uani 1 1 d . . . . .
C6 C 0.8212(8) 0.1150(8) 0.4927(4) 0.0898(17) Uani 1 1 d . . . . .
H6 H 0.857312 0.101391 0.554913 0.108 Uiso 1 1 calc R U . . .
C7 C 0.7739(8) -0.1901(8) 0.4478(4) 0.0849(15) Uani 1 1 d . . . . .
C2 C 0.7158(8) -0.0002(9) 0.3318(4) 0.0963(18) Uani 1 1 d . . . . .
H2 H 0.680428 -0.092613 0.285399 0.116 Uiso 1 1 calc R U . . .
C3 C 0.7149(10) 0.1582(11) 0.3087(6) 0.117(2) Uani 1 1 d . . . . .
H3 H 0.679587 0.173219 0.246560 0.140 Uiso 1 1 calc R U . . .
C4 C 0.7657(12) 0.2936(11) 0.3767(6) 0.124(3) Uani 1 1 d . . . . .
H4 H 0.764134 0.400267 0.360763 0.149 Uiso 1 1 calc R U . . .
C5 C 0.8190(11) 0.2739(10) 0.4680(6) 0.113(2) Uani 1 1 d . . . . .
H5 H 0.853860 0.367211 0.513769 0.136 Uiso 1 1 calc R U . . .
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
O1 0.148(4) 0.108(3) 0.125(3) -0.033(3) -0.031(3) 0.081(3)
C1 0.069(3) 0.077(3) 0.091(3) -0.003(3) 0.003(3) 0.040(3)
C6 0.089(4) 0.082(4) 0.100(4) -0.004(3) 0.010(3) 0.044(3)
C7 0.078(4) 0.083(4) 0.101(4) -0.010(3) -0.003(3) 0.047(3)
C2 0.090(4) 0.106(5) 0.104(4) -0.002(3) -0.003(3) 0.057(4)
C3 0.125(6) 0.122(6) 0.131(5) 0.027(5) 0.014(4) 0.082(5)
C4 0.140(7) 0.102(5) 0.155(7) 0.033(5) 0.042(6) 0.080(5)
C5 0.120(6) 0.081(4) 0.138(6) 0.003(4) 0.031(5) 0.051(4)
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'
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
C6 C1 C2 119.7(6) . . ?
C6 C1 C7 120.5(5) . . ?
C2 C1 C7 119.8(5) . . ?
C1 C6 C5 119.4(6) . . ?
O1 C7 C1 123.3(5) . . ?
O1 C7 C7 116.5(5) . 4_646 ?
C1 C7 C7 120.1(5) . 4_646 ?
C3 C2 C1 120.0(7) . . ?
C4 C3 C2 120.1(7) . . ?
C3 C4 C5 120.5(7) . . ?
C4 C5 C6 120.2(7) . . ?
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
O1 C7 1.218(6) . ?
C1 C6 1.379(7) . ?
C1 C2 1.387(7) . ?
C1 C7 1.466(7) . ?
C6 C5 1.388(9) . ?
C7 C7 1.524(11) 4_646 ?
C2 C3 1.374(9) . ?
C3 C4 1.364(10) . ?
C4 C5 1.366(9) . ?
