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#$Date: 2023-08-05 12:33:29 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285526 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159469.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_7159469
loop_
_publ_author_name
'Dasi, Rajesh'
'Villinger, Alexander'
'Brasholz, Malte'
_publ_section_title
;
 Visible light-induced iridium(III)-sensitized [2 + 2] and [3 + 2]
 photocycloadditions of 2-cyanochromone with alkenes.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6103
_journal_page_last               6106
_journal_paper_doi               10.1039/d3ob00862b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H12 Cl N O2'
_chemical_formula_sum            'C18 H12 Cl N O2'
_chemical_formula_weight         309.74
_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-2014/7
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                114.137(4)
_cell_angle_beta                 98.043(5)
_cell_angle_gamma                97.708(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0634(10)
_cell_length_b                   9.8825(12)
_cell_length_c                   10.1049(13)
_cell_measurement_reflns_used    6564
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.87
_cell_measurement_theta_min      2.31
_cell_volume                     711.10(16)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.991
_diffrn_reflns_theta_min         2.262
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0493P)²+0.2377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3581
_reflns_number_total             4529
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00862b2.cif
_cod_data_source_block           is_rd242cf1
_cod_depositor_comments
'Adding full bibliography for 7159468--7159472.cif.'
_cod_database_code               7159469
_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_min   0.929
_shelx_estimated_absorpt_t_max   0.989
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
Cl1 Cl 0.80286(4) 0.03969(4) 0.91916(4) 0.02718(9) Uani 1 1 d . . . . .
O1 O 0.29088(11) 0.43853(10) 0.58762(10) 0.02110(19) Uani 1 1 d . . . . .
O2 O -0.11553(13) 0.56891(12) 0.78625(13) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.19826(16) 0.06692(13) 0.47441(13) 0.0282(2) Uani 1 1 d . . . . .
C1 C 0.21005(15) 0.35075(13) 0.65169(13) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.28362(15) 0.38983(13) 0.81709(13) 0.0170(2) Uani 1 1 d . . . . .
H2 H 0.3262 0.5021 0.8742 0.020 Uiso 1 1 calc R U . . .
C3 C 0.09707(15) 0.34718(14) 0.83109(14) 0.0197(2) Uani 1 1 d . . . . .
H3A H 0.0690 0.4194 0.9227 0.024 Uiso 1 1 calc R U . . .
H3B H 0.0630 0.2414 0.8171 0.024 Uiso 1 1 calc R U . . .
C4 C 0.03299(15) 0.37088(13) 0.69101(13) 0.0175(2) Uani 1 1 d . . . . .
H4 H -0.0642 0.2882 0.6178 0.021 Uiso 1 1 calc R U . . .
C5 C 0.00172(16) 0.52813(14) 0.72673(14) 0.0199(2) Uani 1 1 d . . . . .
C6 C 0.11792(16) 0.62682(13) 0.68613(13) 0.0188(2) Uani 1 1 d . . . . .
C7 C 0.09157(18) 0.77236(14) 0.71237(14) 0.0233(3) Uani 1 1 d . . . . .
H7 H -0.0042 0.8046 0.7516 0.028 Uiso 1 1 calc R U . . .
C8 C 0.20301(19) 0.86923(14) 0.68194(15) 0.0264(3) Uani 1 1 d . . . . .
H8 H 0.1838 0.9674 0.6999 0.032 Uiso 1 1 calc R U . . .
C9 C 0.34371(19) 0.82241(15) 0.62476(15) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.4212 0.8898 0.6052 0.032 Uiso 1 1 calc R U . . .
C10 C 0.37205(17) 0.67888(15) 0.59604(14) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.4679 0.6474 0.5566 0.028 Uiso 1 1 calc R U . . .
C11 C 0.25790(15) 0.58115(13) 0.62577(13) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.20505(16) 0.19117(14) 0.55040(13) 0.0195(2) Uani 1 1 d . . . . .
C13 C 0.41825(14) 0.31107(13) 0.85203(13) 0.0164(2) Uani 1 1 d . . . . .
C14 C 0.55015(16) 0.28948(15) 0.77438(14) 0.0212(2) Uani 1 1 d . . . . .
H14 H 0.5585 0.3318 0.7058 0.025 Uiso 1 1 calc R U . . .
C15 C 0.66911(15) 0.20718(15) 0.79587(14) 0.0214(2) Uani 1 1 d . . . . .
H15 H 0.7561 0.1900 0.7402 0.026 Uiso 1 1 calc R U . . .
C16 C 0.65893(15) 0.15045(13) 0.89990(14) 0.0195(2) Uani 1 1 d . . . . .
C17 C 0.53513(16) 0.17706(13) 0.98461(13) 0.0193(2) Uani 1 1 d . . . . .
H17 H 0.5334 0.1421 1.0592 0.023 Uiso 1 1 calc R U . . .
C18 C 0.41334(15) 0.25582(13) 0.95850(13) 0.0184(2) Uani 1 1 d . . . . .
H18 H 0.3260 0.2721 1.0139 0.022 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'
Cl Cl 0.1484 0.1585 '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
C11 O1 C1 116.90(9) . . ?
O1 C1 C12 105.27(9) . . ?
O1 C1 C4 120.52(9) . . ?
C12 C1 C4 111.12(10) . . ?
O1 C1 C2 118.36(10) . . ?
C12 C1 C2 112.51(9) . . ?
C4 C1 C2 88.71(9) . . ?
C13 C2 C3 120.85(10) . . ?
C13 C2 C1 118.95(10) . . ?
C3 C2 C1 87.59(9) . . ?
C13 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C2 C3 C4 88.84(9) . . ?
C2 C3 H3A 113.8 . . ?
C4 C3 H3A 113.8 . . ?
C2 C3 H3B 113.8 . . ?
C4 C3 H3B 113.8 . . ?
H3A C3 H3B 111.1 . . ?
C5 C4 C1 113.15(10) . . ?
C5 C4 C3 113.57(10) . . ?
C1 C4 C3 87.54(9) . . ?
C5 C4 H4 113.4 . . ?
C1 C4 H4 113.4 . . ?
C3 C4 H4 113.4 . . ?
O2 C5 C6 122.68(11) . . ?
O2 C5 C4 120.03(11) . . ?
C6 C5 C4 117.29(10) . . ?
C11 C6 C7 118.42(11) . . ?
C11 C6 C5 121.79(11) . . ?
C7 C6 C5 119.77(11) . . ?
C8 C7 C6 120.83(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.73(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.80(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.10(13) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O1 C11 C10 115.34(11) . . ?
O1 C11 C6 123.53(11) . . ?
C10 C11 C6 121.09(11) . . ?
N1 C12 C1 178.10(14) . . ?
C18 C13 C14 118.83(11) . . ?
C18 C13 C2 121.61(10) . . ?
C14 C13 C2 119.55(10) . . ?
C15 C14 C13 121.01(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 118.92(11) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.43(11) . . ?
C15 C16 Cl1 118.32(10) . . ?
C17 C16 Cl1 120.24(10) . . ?
C16 C17 C18 118.93(11) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.74(11) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 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
Cl1 C16 1.7421(12) . ?
O1 C11 1.3750(14) . ?
O1 C1 1.4221(14) . ?
O2 C5 1.2170(15) . ?
N1 C12 1.1399(17) . ?
C1 C12 1.4790(17) . ?
C1 C4 1.5512(16) . ?
C1 C2 1.5581(17) . ?
C2 C13 1.5010(16) . ?
C2 C3 1.5487(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5571(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5102(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.4789(17) . ?
C6 C11 1.3978(17) . ?
C6 C7 1.4035(17) . ?
C7 C8 1.3805(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3847(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3951(17) . ?
C10 H10 0.9500 . ?
C13 C18 1.3942(16) . ?
C13 C14 1.3963(17) . ?
C14 C15 1.3871(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3856(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3871(17) . ?
C17 C18 1.3929(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
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
C11 O1 C1 C12 156.98(10) . . . . ?
C11 O1 C1 C4 30.51(15) . . . . ?
C11 O1 C1 C2 -76.26(13) . . . . ?
O1 C1 C2 C13 -91.01(12) . . . . ?
C12 C1 C2 C13 32.20(14) . . . . ?
C4 C1 C2 C13 144.58(10) . . . . ?
O1 C1 C2 C3 144.72(10) . . . . ?
C12 C1 C2 C3 -92.08(10) . . . . ?
C4 C1 C2 C3 20.30(8) . . . . ?
C13 C2 C3 C4 -142.85(11) . . . . ?
C1 C2 C3 C4 -20.22(8) . . . . ?
O1 C1 C4 C5 -28.13(15) . . . . ?
C12 C1 C4 C5 -151.86(10) . . . . ?
C2 C1 C4 C5 94.44(10) . . . . ?
O1 C1 C4 C3 -142.76(11) . . . . ?
C12 C1 C4 C3 93.50(10) . . . . ?
C2 C1 C4 C3 -20.19(8) . . . . ?
C2 C3 C4 C5 -93.93(11) . . . . ?
C2 C3 C4 C1 20.32(8) . . . . ?
C1 C4 C5 O2 -166.01(11) . . . . ?
C3 C4 C5 O2 -68.22(15) . . . . ?
C1 C4 C5 C6 14.14(15) . . . . ?
C3 C4 C5 C6 111.94(12) . . . . ?
O2 C5 C6 C11 176.19(12) . . . . ?
C4 C5 C6 C11 -3.97(17) . . . . ?
O2 C5 C6 C7 -1.86(19) . . . . ?
C4 C5 C6 C7 177.98(11) . . . . ?
C11 C6 C7 C8 -1.20(18) . . . . ?
C5 C6 C7 C8 176.92(11) . . . . ?
C6 C7 C8 C9 -0.13(19) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -0.29(19) . . . . ?
C1 O1 C11 C10 163.05(10) . . . . ?
C1 O1 C11 C6 -18.83(16) . . . . ?
C9 C10 C11 O1 177.08(11) . . . . ?
C9 C10 C11 C6 -1.10(19) . . . . ?
C7 C6 C11 O1 -176.20(11) . . . . ?
C5 C6 C11 O1 5.72(18) . . . . ?
C7 C6 C11 C10 1.83(18) . . . . ?
C5 C6 C11 C10 -176.25(11) . . . . ?
C3 C2 C13 C18 -30.94(16) . . . . ?
C1 C2 C13 C18 -136.87(11) . . . . ?
C3 C2 C13 C14 147.76(11) . . . . ?
C1 C2 C13 C14 41.83(15) . . . . ?
C18 C13 C14 C15 3.65(18) . . . . ?
C2 C13 C14 C15 -175.08(11) . . . . ?
C13 C14 C15 C16 -2.18(19) . . . . ?
C14 C15 C16 C17 -1.41(19) . . . . ?
C14 C15 C16 Cl1 176.97(10) . . . . ?
C15 C16 C17 C18 3.39(18) . . . . ?
Cl1 C16 C17 C18 -174.95(9) . . . . ?
C16 C17 C18 C13 -1.84(18) . . . . ?
C14 C13 C18 C17 -1.61(18) . . . . ?
C2 C13 C18 C17 177.10(11) . . . . ?
