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#$Date: 2023-07-20 00:54:54 +0300 (Thu, 20 Jul 2023) $
#$Revision: 285274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/19/7131901.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_7131901
loop_
_publ_author_name
'Kotipalli, Ramesh'
'Undamatla, Suribabu'
'Nanubolu, Jagadesh Babu'
'Maddi, Sridhar Reddy'
_publ_section_title
;
 Rh-Catalyzed Chemo-, Stereo- and Regioselective C-H Cascade Annulation of
 indolyloxopropanenitriles for Pyranoindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02762G
_journal_year                    2023
_chemical_formula_moiety         'C22 H14 N2 O3'
_chemical_formula_sum            'C22 H14 N2 O3'
_chemical_formula_weight         354.35
_chemical_name_systematic
(Z)-2-(1-methyl-3-oxo-1-phenyl-3,10-dihydrofuro[3',4':5,6]pyrano[4,3-b]indol-5(1H)-ylidene)acetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.143(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8625(12)
_cell_length_b                   24.973(3)
_cell_length_c                   7.5384(10)
_cell_measurement_reflns_used    6240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.916
_cell_measurement_theta_min      2.359
_cell_volume                     1731.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22582
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.055
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0394
_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)+(0.0436P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                2359
_reflns_number_total             3617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02762g2.cif
_cod_data_source_block           KB658_0m_a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7131901
_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   0.969
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
O1 O 0.58891(19) 0.57657(8) 0.5502(3) 0.0420(6) Uani 1 1 d . . . . .
O2 O 0.1486(2) 0.65966(8) 0.1876(3) 0.0589(7) Uani 1 1 d . . . . .
O3 O 0.3744(2) 0.69091(8) 0.3416(3) 0.0504(6) Uani 1 1 d . . . . .
N1 N 0.1845(3) 0.52010(10) 0.2164(4) 0.0408(7) Uani 1 1 d . . . . .
N2 N 0.8993(3) 0.52910(14) 0.8980(5) 0.0725(10) Uani 1 1 d . . . . .
C1 C 0.2038(3) 0.46504(12) 0.2381(4) 0.0379(7) Uani 1 1 d . . . . .
C2 C 0.1061(3) 0.42421(13) 0.1578(5) 0.0506(9) Uani 1 1 d . . . . .
H2 H 0.012516 0.431547 0.073674 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1516(4) 0.37261(13) 0.2063(5) 0.0574(10) Uani 1 1 d . . . . .
H3 H 0.087237 0.344538 0.156020 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2925(4) 0.36139(14) 0.3292(5) 0.0551(9) Uani 1 1 d . . . . .
H4 H 0.320909 0.325951 0.357938 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3900(3) 0.40171(12) 0.4087(5) 0.0461(8) Uani 1 1 d . . . . .
H5 H 0.483783 0.393705 0.490592 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3469(3) 0.45497(11) 0.3654(4) 0.0360(7) Uani 1 1 d . . . . .
C7 C 0.4127(3) 0.50660(11) 0.4190(4) 0.0336(7) Uani 1 1 d . . . . .
C8 C 0.3092(3) 0.54433(12) 0.3234(4) 0.0339(7) Uani 1 1 d . . . . .
C9 C 0.5538(3) 0.52217(11) 0.5451(4) 0.0364(7) Uani 1 1 d . . . . .
C10 C 0.6604(3) 0.49146(12) 0.6649(5) 0.0448(8) Uani 1 1 d . . . . .
H10 H 0.646295 0.454624 0.663898 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7918(4) 0.51280(14) 0.7911(5) 0.0526(9) Uani 1 1 d . . . . .
C12 C 0.4859(3) 0.61165(12) 0.4502(4) 0.0381(7) Uani 1 1 d . . . . .
C13 C 0.3487(3) 0.59964(11) 0.3446(4) 0.0358(7) Uani 1 1 d . . . . .
C14 C 0.2736(3) 0.65013(12) 0.2778(4) 0.0440(8) Uani 1 1 d . . . . .
C15 C 0.5196(3) 0.67002(12) 0.4461(4) 0.0427(8) Uani 1 1 d . . . . .
C16 C 0.5795(4) 0.69517(14) 0.6405(5) 0.0591(9) Uani 1 1 d . . . . .
H16A H 0.591758 0.732939 0.627995 0.089 Uiso 1 1 calc R U . . .
H16B H 0.671696 0.679286 0.711978 0.089 Uiso 1 1 calc R U . . .
H16C H 0.513065 0.689314 0.705492 0.089 Uiso 1 1 calc R U . . .
C17 C 0.6173(3) 0.68125(12) 0.3322(4) 0.0426(7) Uani 1 1 d . . . . .
C18 C 0.7448(3) 0.65249(14) 0.3692(5) 0.0600(10) Uani 1 1 d . . . . .
H18 H 0.770500 0.626200 0.462847 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8340(4) 0.66273(16) 0.2671(6) 0.0656(10) Uani 1 1 d . . . . .
H19 H 0.918548 0.642847 0.291844 0.079 Uiso 1 1 calc R U . . .
C20 C 0.7995(4) 0.70148(16) 0.1313(5) 0.0618(10) Uani 1 1 d . . . . .
H20 H 0.859495 0.707961 0.062633 0.074 Uiso 1 1 calc R U . . .
C21 C 0.6745(5) 0.73101(14) 0.0966(5) 0.0615(10) Uani 1 1 d . . . . .
H21 H 0.651783 0.758210 0.006283 0.074 Uiso 1 1 calc R U . . .
C22 C 0.5822(4) 0.72081(12) 0.1942(5) 0.0522(9) Uani 1 1 d . . . . .
H22 H 0.497024 0.740445 0.167165 0.063 Uiso 1 1 calc R U . . .
H1N H 0.100(5) 0.5346(17) 0.134(7) 0.102(15) Uiso 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
C12 O1 C9 119.1(2) . . ?
C14 O3 C15 111.5(2) . . ?
C8 N1 C1 108.5(3) . . ?
C2 C1 N1 129.3(3) . . ?
C2 C1 C6 122.2(3) . . ?
N1 C1 C6 108.5(3) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 136.1(3) . . ?
C1 C6 C7 105.7(2) . . ?
C8 C7 C9 121.3(2) . . ?
C8 C7 C6 106.9(2) . . ?
C9 C7 C6 131.8(3) . . ?
N1 C8 C7 110.4(2) . . ?
N1 C8 C13 130.9(3) . . ?
C7 C8 C13 118.7(2) . . ?
C10 C9 O1 114.0(3) . . ?
C10 C9 C7 128.9(3) . . ?
O1 C9 C7 117.1(2) . . ?
C9 C10 C11 122.8(3) . . ?
N2 C11 C10 178.0(4) . . ?
C13 C12 O1 125.9(3) . . ?
C13 C12 C15 113.1(3) . . ?
O1 C12 C15 121.1(3) . . ?
C12 C13 C8 117.5(2) . . ?
C12 C13 C14 106.9(3) . . ?
C8 C13 C14 135.6(3) . . ?
O2 C14 O3 121.0(3) . . ?
O2 C14 C13 131.2(3) . . ?
O3 C14 C13 107.8(3) . . ?
O3 C15 C12 100.2(2) . . ?
O3 C15 C16 109.9(3) . . ?
C12 C15 C16 113.4(3) . . ?
O3 C15 C17 109.0(2) . . ?
C12 C15 C17 112.3(3) . . ?
C16 C15 C17 111.4(2) . . ?
C22 C17 C18 118.9(3) . . ?
C22 C17 C15 121.0(3) . . ?
C18 C17 C15 120.1(3) . . ?
C19 C18 C17 120.3(3) . . ?
C20 C19 C18 120.9(3) . . ?
C19 C20 C21 119.2(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 C17 119.8(3) . . ?
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 C12 1.347(3) . ?
O1 C9 1.399(3) . ?
O2 C14 1.198(4) . ?
O3 C14 1.382(4) . ?
O3 C15 1.460(3) . ?
N1 C8 1.347(4) . ?
N1 C1 1.390(4) . ?
N2 C11 1.150(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.413(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.392(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.399(4) . ?
C6 C7 1.435(4) . ?
C7 C8 1.385(4) . ?
C7 C9 1.427(4) . ?
C8 C13 1.428(4) . ?
C9 C10 1.351(4) . ?
C10 C11 1.407(5) . ?
C12 C13 1.333(4) . ?
C12 C15 1.498(4) . ?
C13 C14 1.457(4) . ?
C15 C16 1.505(5) . ?
C15 C17 1.530(4) . ?
C17 C22 1.385(4) . ?
C17 C18 1.386(4) . ?
C18 C19 1.386(5) . ?
C19 C20 1.360(5) . ?
C20 C21 1.378(5) . ?
C21 C22 1.385(5) . ?
