#------------------------------------------------------------------------------
#$Date: 2023-03-01 09:37:38 +0200 (Wed, 01 Mar 2023) $
#$Revision: 281179 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/13/7131339.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_7131339
loop_
_publ_author_name
'Dhanaji, Jadhav Rahul'
'Samatha, Polasani'
'Raju, Silver'
'Mainkar, Prathama S.'
'Adepu, Raju'
'Chandrasekhar, Srivari'
_publ_section_title
;
 Substitution controlled aryne insertion: synthesis of
 diarylmethane/chromones.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2648
_journal_page_last               2651
_journal_paper_doi               10.1039/d2cc05992d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C24 H18 N2 O5'
_chemical_formula_weight         414.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-10 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                81.178(2)
_cell_angle_beta                 89.732(3)
_cell_angle_gamma                83.318(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1443(5)
_cell_length_b                   9.6794(6)
_cell_length_c                   13.0717(8)
_cell_measurement_reflns_used    6140
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.5
_cell_volume                     1011.27(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III-C7'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.482
_diffrn_reflns_theta_min         2.458
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       Plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0558
_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)+(0.0708P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             6140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc05992d2.cif
_cod_data_source_block           datam
_cod_database_code               7131339
_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   0.970
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.4388(2) 0.15890(18) 0.74730(13) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.5161(3) 0.0277(2) 0.78985(15) 0.0551(5) Uani 1 1 d . . . . .
H2 H 0.503735 -0.004451 0.859925 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6111(3) -0.0564(2) 0.73029(17) 0.0606(6) Uani 1 1 d . . . . .
H3 H 0.662146 -0.144001 0.760603 0.073 Uiso 1 1 calc R U . . .
C4 C 0.6304(3) -0.0117(2) 0.62729(17) 0.0615(6) Uani 1 1 d . . . . .
H4 H 0.696532 -0.067225 0.587554 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5508(3) 0.1165(2) 0.58280(15) 0.0566(5) Uani 1 1 d . . . . .
H5 H 0.562242 0.145913 0.512246 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4537(2) 0.20350(18) 0.64066(13) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.3670(2) 0.3395(2) 0.58650(14) 0.0495(5) Uani 1 1 d . . . . .
C8 C 0.2836(3) 0.4688(2) 0.41923(17) 0.0737(7) Uani 1 1 d . . . . .
H8A H 0.350638 0.502981 0.361405 0.088 Uiso 1 1 calc R U . . .
H8B H 0.256202 0.544423 0.459417 0.088 Uiso 1 1 calc R U . . .
C9 C 0.1311(3) 0.4257(3) 0.38052(19) 0.0829(7) Uani 1 1 d . . . . .
H9A H 0.072382 0.503661 0.335962 0.124 Uiso 1 1 calc R U . . .
H9B H 0.062718 0.396121 0.437889 0.124 Uiso 1 1 calc R U . . .
H9C H 0.158643 0.349043 0.342427 0.124 Uiso 1 1 calc R U . . .
C10 C 0.3507(2) 0.25504(18) 0.81810(13) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.253187 0.307818 0.781016 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2958(3) 0.1748(2) 0.91367(16) 0.0567(5) Uani 1 1 d . . . . .
C12 C 0.4642(2) 0.36111(18) 0.84496(12) 0.0432(4) Uani 1 1 d . . . . .
C13 C 0.4042(2) 0.50124(19) 0.85053(13) 0.0435(4) Uani 1 1 d . . . . .
C14 C 0.5144(2) 0.5941(2) 0.87054(14) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.475151 0.687705 0.872718 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6807(2) 0.5497(2) 0.88716(15) 0.0565(5) Uani 1 1 d . . . . .
H15 H 0.752623 0.612297 0.901635 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7386(2) 0.4117(2) 0.88205(15) 0.0583(5) Uani 1 1 d . . . . .
H16 H 0.850484 0.380752 0.893113 0.070 Uiso 1 1 calc R U . . .
C17 C 0.6323(2) 0.3192(2) 0.86070(14) 0.0519(5) Uani 1 1 d . . . . .
H17 H 0.673780 0.226571 0.856698 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2248(2) 0.5535(2) 0.84479(14) 0.0493(5) Uani 1 1 d . . . . .
C19 C 0.1735(2) 0.7036(2) 0.79849(14) 0.0493(5) Uani 1 1 d . . . . .
C20 C 0.2226(3) 0.7573(2) 0.70054(16) 0.0631(6) Uani 1 1 d . . . . .
H20 H 0.294127 0.701279 0.663974 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1666(3) 0.8927(2) 0.65675(16) 0.0645(6) Uani 1 1 d . . . . .
H21 H 0.194875 0.927425 0.589485 0.077 Uiso 1 1 calc R U . . .
C22 C 0.0678(2) 0.9758(2) 0.71434(16) 0.0550(5) Uani 1 1 d . . . . .
C23 C 0.0197(3) 0.9272(2) 0.81257(16) 0.0618(6) Uani 1 1 d . . . . .
H23 H -0.045335 0.985768 0.850672 0.074 Uiso 1 1 calc R U . . .
C24 C 0.0706(2) 0.7888(2) 0.85340(15) 0.0594(5) Uani 1 1 d . . . . .
H24 H 0.035182 0.752331 0.918691 0.071 Uiso 1 1 calc R U . . .
N1 N 0.2535(3) 0.1129(2) 0.98909(15) 0.0847(6) Uani 1 1 d . . . . .
N2 N 0.0109(2) 1.12189(19) 0.66849(18) 0.0730(5) Uani 1 1 d . . . . .
O1 O 0.29686(19) 0.43057(14) 0.62838(11) 0.0720(5) Uani 1 1 d . . . . .
O2 O 0.37666(19) 0.34796(14) 0.48420(10) 0.0699(4) Uani 1 1 d . . . . .
O3 O 0.12078(17) 0.47909(14) 0.87948(11) 0.0637(4) Uani 1 1 d . . . . .
O4 O -0.0536(3) 1.20041(17) 0.72485(16) 0.1131(7) Uani 1 1 d . . . . .
O5 O 0.0320(3) 1.15744(18) 0.57711(16) 0.1076(7) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.56(15) . . ?
C2 C1 C10 119.53(16) . . ?
C6 C1 C10 121.77(16) . . ?
C3 C2 C1 121.34(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 120.34(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.28(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.73(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.69(17) . . ?
C5 C6 C7 118.76(17) . . ?
C1 C6 C7 122.54(15) . . ?
O1 C7 O2 123.27(18) . . ?
O1 C7 C6 125.21(17) . . ?
O2 C7 C6 111.53(15) . . ?
O2 C8 C9 109.51(18) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 111.84(15) . . ?
C11 C10 C12 109.46(14) . . ?
C1 C10 C12 110.66(14) . . ?
C11 C10 H10 108.3 . . ?
C1 C10 H10 108.3 . . ?
C12 C10 H10 108.3 . . ?
N1 C11 C10 179.2(2) . . ?
C17 C12 C13 118.49(16) . . ?
C17 C12 C10 119.59(16) . . ?
C13 C12 C10 121.88(16) . . ?
C14 C13 C12 119.23(17) . . ?
C14 C13 C18 117.84(16) . . ?
C12 C13 C18 122.73(16) . . ?
C15 C14 C13 121.28(18) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.13(18) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.42(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.44(18) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O3 C18 C13 121.75(18) . . ?
O3 C18 C19 119.78(17) . . ?
C13 C18 C19 118.43(17) . . ?
C20 C19 C24 119.35(19) . . ?
C20 C19 C18 121.23(16) . . ?
C24 C19 C18 119.39(17) . . ?
C21 C20 C19 120.51(18) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 118.67(19) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 122.37(19) . . ?
C23 C22 N2 118.86(18) . . ?
C21 C22 N2 118.77(19) . . ?
C22 C23 C24 118.13(17) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C23 C24 C19 120.85(19) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O5 N2 O4 123.6(2) . . ?
O5 N2 C22 118.33(19) . . ?
O4 N2 C22 118.0(2) . . ?
C7 O2 C8 118.40(15) . . ?
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
C1 C2 1.385(2) . ?
C1 C6 1.404(2) . ?
C1 C10 1.530(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(3) . ?
C7 O1 1.196(2) . ?
C7 O2 1.330(2) . ?
C8 O2 1.469(2) . ?
C8 C9 1.471(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.464(3) . ?
C10 C12 1.538(2) . ?
C10 H10 0.9800 . ?
C11 N1 1.146(2) . ?
C12 C17 1.388(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.487(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.217(2) . ?
C18 C19 1.498(3) . ?
C19 C20 1.381(3) . ?
C19 C24 1.383(2) . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 N2 1.471(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N2 O5 1.209(2) . ?
N2 O4 1.213(2) . ?
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
C6 C1 C2 C3 2.4(3) . . . . ?
C10 C1 C2 C3 -173.34(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -178.24(18) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C10 C1 C6 C5 173.04(16) . . . . ?
C2 C1 C6 C7 176.38(16) . . . . ?
C10 C1 C6 C7 -8.0(3) . . . . ?
C5 C6 C7 O1 -170.49(19) . . . . ?
C1 C6 C7 O1 10.6(3) . . . . ?
C5 C6 C7 O2 9.6(2) . . . . ?
C1 C6 C7 O2 -169.35(17) . . . . ?
C2 C1 C10 C11 -25.9(2) . . . . ?
C6 C1 C10 C11 158.59(17) . . . . ?
C2 C1 C10 C12 96.47(19) . . . . ?
C6 C1 C10 C12 -79.1(2) . . . . ?
C11 C10 C12 C17 86.69(19) . . . . ?
C1 C10 C12 C17 -37.0(2) . . . . ?
C11 C10 C12 C13 -95.64(19) . . . . ?
C1 C10 C12 C13 140.65(16) . . . . ?
C17 C12 C13 C14 0.6(2) . . . . ?
C10 C12 C13 C14 -177.06(15) . . . . ?
C17 C12 C13 C18 -174.07(16) . . . . ?
C10 C12 C13 C18 8.2(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C18 C13 C14 C15 173.52(17) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C10 C12 C17 C16 178.21(16) . . . . ?
C14 C13 C18 O3 -141.76(18) . . . . ?
C12 C13 C18 O3 33.0(3) . . . . ?
C14 C13 C18 C19 35.9(2) . . . . ?
C12 C13 C18 C19 -149.33(16) . . . . ?
O3 C18 C19 C20 -127.6(2) . . . . ?
C13 C18 C19 C20 54.7(2) . . . . ?
O3 C18 C19 C24 50.2(3) . . . . ?
C13 C18 C19 C24 -127.48(18) . . . . ?
C24 C19 C20 C21 -1.7(3) . . . . ?
C18 C19 C20 C21 176.15(18) . . . . ?
C19 C20 C21 C22 3.3(3) . . . . ?
C20 C21 C22 C23 -1.8(3) . . . . ?
C20 C21 C22 N2 178.55(19) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
N2 C22 C23 C24 178.33(19) . . . . ?
C22 C23 C24 C19 3.0(3) . . . . ?
C20 C19 C24 C23 -1.5(3) . . . . ?
C18 C19 C24 C23 -179.40(18) . . . . ?
C23 C22 N2 O5 -168.8(2) . . . . ?
C21 C22 N2 O5 10.8(3) . . . . ?
C23 C22 N2 O4 11.8(3) . . . . ?
C21 C22 N2 O4 -168.6(2) . . . . ?
O1 C7 O2 C8 -6.0(3) . . . . ?
C6 C7 O2 C8 173.90(17) . . . . ?
C9 C8 O2 C7 -100.8(2) . . . . ?
