#------------------------------------------------------------------------------
#$Date: 2024-10-06 12:18:46 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160124.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_7160124
loop_
_publ_author_name
'Manna, Sabyasachi'
'Sreedhara, Rahul Halanuru'
'Prabhu, Kandikere Ramaiah'
_publ_section_title
;
 Visible light-mediated radical addition cascade cyclization of aryl
 isocyanides with tricarbonyls: rapid access to substituted
 phenanthridines and isoquinolines.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7786
_journal_page_last               7790
_journal_paper_doi               10.1039/d4ob01405g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C24 H25 N O6'
_chemical_formula_weight         423.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-03-30 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.174(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8789(9)
_cell_length_b                   14.2204(13)
_cell_length_c                   10.1298(19)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5421
_cell_measurement_theta_min      2.7526
_cell_volume                     1065.3(3)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37464
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_min         3.105
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 2814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0336
_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)+(0.0591P)²+0.0875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6269
_reflns_number_total             6437
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01405g3.cif
_cod_data_source_block           338_b_reduced1_a
_cod_depositor_comments          'Adding full bibliography for 7160124.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160124
_shelx_shelxl_version_number     2019/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O2 O 0.51079(15) 0.51461(8) -0.04108(11) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.69444(15) 0.67789(8) 0.09810(11) 0.0149(2) Uani 1 1 d . . . . .
O4 O 0.24600(16) 0.49733(9) 0.08434(12) 0.0206(2) Uani 1 1 d . . . . .
O5 O 0.73146(16) 0.44477(8) 0.13429(12) 0.0187(2) Uani 1 1 d . . . . .
O6 O 0.44018(16) 0.72507(8) 0.13397(13) 0.0183(2) Uani 1 1 d . . . . .
O1 O 0.31344(15) 0.57903(9) 0.28530(13) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.76602(17) 0.63442(9) 0.38941(13) 0.0127(2) Uani 1 1 d . . . . .
C1 C 0.88393(19) 0.63725(11) 0.52741(15) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.90653(19) 0.56078(11) 0.62033(16) 0.0142(3) Uani 1 1 d . . . . .
C3 C 1.0261(2) 0.57205(12) 0.75990(16) 0.0189(3) Uani 1 1 d . . . . .
H3 H 1.043760 0.521627 0.824795 0.023 Uiso 1 1 calc R U . . .
C4 C 1.1170(2) 0.65529(13) 0.80278(17) 0.0208(3) Uani 1 1 d . . . . .
H4 H 1.196838 0.661550 0.897151 0.025 Uiso 1 1 calc R U . . .
C5 C 1.0943(2) 0.73105(13) 0.70994(17) 0.0203(3) Uani 1 1 d . . . . .
H5 H 1.157981 0.788202 0.741082 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9785(2) 0.72193(11) 0.57271(17) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.962742 0.772844 0.508856 0.021 Uiso 1 1 calc R U . . .
C7 C 0.80536(19) 0.47566(11) 0.56728(15) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.68692(19) 0.47394(10) 0.42608(15) 0.0124(2) Uani 1 1 d . . . . .
C9 C 0.67465(18) 0.55805(10) 0.34255(14) 0.0115(2) Uani 1 1 d . . . . .
C10 C 0.5857(2) 0.39188(11) 0.37334(16) 0.0145(3) Uani 1 1 d . . . . .
H10 H 0.507152 0.390637 0.278067 0.017 Uiso 1 1 calc R U . . .
C11 C 0.5973(2) 0.31321(11) 0.45621(18) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.7145(2) 0.31618(11) 0.59638(17) 0.0195(3) Uani 1 1 d . . . . .
H12 H 0.723101 0.263066 0.655205 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8171(2) 0.39440(12) 0.65015(16) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.897496 0.393877 0.744862 0.021 Uiso 1 1 calc R U . . .
C14 C 0.54626(18) 0.56405(10) 0.18957(14) 0.0112(2) Uani 1 1 d . . . . .
C15 C 0.3495(2) 0.54213(10) 0.17750(16) 0.0134(3) Uani 1 1 d . . . . .
C16 C 0.1338(2) 0.55911(13) 0.2913(2) 0.0235(3) Uani 1 1 d . . . . .
H16A H 0.042324 0.564042 0.195804 0.028 Uiso 1 1 calc R U . . .
H16B H 0.104100 0.606220 0.351974 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1277(2) 0.46206(14) 0.34893(17) 0.0219(3) Uani 1 1 d . . . . .
H17A H 0.012139 0.453141 0.363648 0.033 Uiso 1 1 calc R U . . .
H17B H 0.227199 0.454817 0.438682 0.033 Uiso 1 1 calc R U . . .
H17C H 0.139643 0.415049 0.281945 0.033 Uiso 1 1 calc R U . . .
C18 C 0.4883(3) 0.22665(12) 0.3961(2) 0.0240(3) Uani 1 1 d . . . . .
H18A H 0.512568 0.178252 0.469123 0.036 Uiso 1 1 calc R U . . .
H18B H 0.522124 0.202923 0.317704 0.036 Uiso 1 1 calc R U . . .
H18C H 0.359312 0.242366 0.362143 0.036 Uiso 1 1 calc R U . . .
C19 C 0.60802(19) 0.49916(10) 0.09274(15) 0.0124(2) Uani 1 1 d . . . . .
C20 C 0.5721(2) 0.46623(12) -0.14340(16) 0.0180(3) Uani 1 1 d . . . . .
H20A H 0.599809 0.399634 -0.115903 0.022 Uiso 1 1 calc R U . . .
H20B H 0.682811 0.496486 -0.148551 0.022 Uiso 1 1 calc R U . . .
C21 C 0.4219(2) 0.47237(13) -0.28331(16) 0.0208(3) Uani 1 1 d . . . . .
H21A H 0.463027 0.446077 -0.356532 0.031 Uiso 1 1 calc R U . . .
H21B H 0.387638 0.538345 -0.304978 0.031 Uiso 1 1 calc R U . . .
H21C H 0.317225 0.436700 -0.279649 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5517(2) 0.66642(10) 0.13843(14) 0.0131(3) Uani 1 1 d . . . . .
C23 C 0.7222(2) 0.77235(11) 0.05443(19) 0.0211(3) Uani 1 1 d . . . . .
H23A H 0.746688 0.816694 0.134177 0.025 Uiso 1 1 calc R U . . .
H23B H 0.613372 0.794005 -0.022821 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8818(3) 0.76779(13) 0.0054(2) 0.0243(3) Uani 1 1 d . . . . .
H24A H 0.904707 0.830323 -0.025557 0.036 Uiso 1 1 calc R U . . .
H24B H 0.856084 0.723465 -0.073181 0.036 Uiso 1 1 calc R U . . .
H24C H 0.988694 0.746611 0.082929 0.036 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'
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
C19 O2 C20 115.63(12) . . ?
C22 O3 C23 115.98(12) . . ?
C15 O1 C16 116.21(13) . . ?
C9 N1 C1 119.13(13) . . ?
N1 C1 C6 116.67(13) . . ?
N1 C1 C2 122.51(13) . . ?
C6 C1 C2 120.80(13) . . ?
C1 C2 C3 117.93(14) . . ?
C1 C2 C7 118.10(13) . . ?
C3 C2 C7 123.96(14) . . ?
C4 C3 C2 120.62(15) . . ?
C3 C4 C5 121.22(14) . . ?
C6 C5 C4 119.40(15) . . ?
C5 C6 C1 120.02(15) . . ?
C13 C7 C8 118.19(14) . . ?
C13 C7 C2 123.29(13) . . ?
C8 C7 C2 118.51(13) . . ?
C10 C8 C7 119.18(13) . . ?
C10 C8 C9 123.13(13) . . ?
C7 C8 C9 117.68(12) . . ?
N1 C9 C8 124.04(13) . . ?
N1 C9 C14 114.34(12) . . ?
C8 C9 C14 121.60(12) . . ?
C11 C10 C8 121.94(14) . . ?
C10 C11 C12 118.22(14) . . ?
C10 C11 C18 120.47(15) . . ?
C12 C11 C18 121.30(15) . . ?
C13 C12 C11 121.23(14) . . ?
C12 C13 C7 121.21(14) . . ?
C9 C14 C19 111.50(11) . . ?
C9 C14 C15 111.29(11) . . ?
C19 C14 C15 110.92(11) . . ?
C9 C14 C22 107.77(11) . . ?
C19 C14 C22 107.34(11) . . ?
C15 C14 C22 107.80(11) . . ?
O4 C15 O1 125.35(14) . . ?
O4 C15 C14 124.23(14) . . ?
O1 C15 C14 110.41(12) . . ?
O1 C16 C17 110.74(14) . . ?
O5 C19 O2 125.34(13) . . ?
O5 C19 C14 123.92(13) . . ?
O2 C19 C14 110.69(12) . . ?
O2 C20 C21 107.26(12) . . ?
O6 C22 O3 125.98(14) . . ?
O6 C22 C14 124.08(13) . . ?
O3 C22 C14 109.93(12) . . ?
O3 C23 C24 106.95(13) . . ?
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
O2 C19 1.3253(17) . ?
O2 C20 1.4582(18) . ?
O3 C22 1.3323(18) . ?
O3 C23 1.4542(18) . ?
O4 C15 1.1961(19) . ?
O5 C19 1.1995(18) . ?
O6 C22 1.2010(19) . ?
O1 C15 1.3275(19) . ?
O1 C16 1.4650(19) . ?
N1 C9 1.2989(19) . ?
N1 C1 1.3867(18) . ?
C1 C6 1.407(2) . ?
C1 C2 1.409(2) . ?
C2 C3 1.412(2) . ?
C2 C7 1.447(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.400(3) . ?
C5 C6 1.381(2) . ?
C7 C13 1.412(2) . ?
C7 C8 1.4130(19) . ?
C8 C10 1.411(2) . ?
C8 C9 1.449(2) . ?
C9 C14 1.5333(19) . ?
C10 C11 1.383(2) . ?
C11 C12 1.402(2) . ?
C11 C18 1.504(2) . ?
C12 C13 1.372(2) . ?
C14 C19 1.543(2) . ?
C14 C15 1.544(2) . ?
C14 C22 1.5507(19) . ?
C16 C17 1.506(3) . ?
C20 C21 1.503(2) . ?
C23 C24 1.504(2) . ?
