#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/50/4035062.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_4035062
loop_
_publ_author_name
'Ghosh, Koushik'
'Shankar, Majji'
'Rit, Raja K.'
'Dubey, Gurudutt'
'Bharatam, Prasad V.'
'Sahoo, Akhila K.'
_publ_section_title
;
 Sulfoximine-Assisted One-Pot Unsymmetrical Multiple Annulation of Arenes:
 A Combined Experimental and Computational Study.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9667
_journal_page_last               9681
_journal_paper_doi               10.1021/acs.joc.8b01077
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C26 H23 N O2'
_chemical_formula_weight         381.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.372(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6257(12)
_cell_length_b                   15.9625(15)
_cell_length_c                   20.5960(19)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.37
_cell_volume                     4116.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47151
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         9916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0884P)²+0.4486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1954
_reflns_number_gt                4973
_reflns_number_total             9916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01077_si_002.cif
_cod_data_source_block           raja
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O4 O 0.80074(13) 0.93567(9) -0.05268(7) 0.0657(5) Uani 1 1 d .
N1 N 0.18089(14) 0.89419(10) 0.01537(8) 0.0501(4) Uani 1 1 d .
H1 H 0.1787 0.9460 0.0265 0.060 Uiso 1 1 calc R
N2 N 0.69920(14) 0.89853(10) 0.02439(8) 0.0528(5) Uani 1 1 d .
H2 H 0.7023 0.9495 0.0380 0.063 Uiso 1 1 calc R
O2 O 0.28095(13) 0.93117(9) -0.06265(8) 0.0647(4) Uani 1 1 d .
C5 C 0.12849(15) 0.83754(13) 0.05016(10) 0.0452(5) Uani 1 1 d .
C6 C 0.23591(15) 0.78657(12) -0.05473(9) 0.0421(5) Uani 1 1 d .
C7 C 0.21375(19) 0.62260(14) -0.10163(11) 0.0598(6) Uani 1 1 d .
H7 H 0.2065 0.5688 -0.1190 0.072 Uiso 1 1 calc R
C8 C 0.64290(16) 0.84231(13) 0.05733(10) 0.0476(5) Uani 1 1 d .
C9 C 0.63973(16) 0.75993(13) 0.04047(10) 0.0479(5) Uani 1 1 d .
C10 C 0.17162(15) 0.72802(12) -0.02416(9) 0.0439(5) Uani 1 1 d .
C11 C 0.69518(16) 0.73146(12) -0.01327(10) 0.0469(5) Uani 1 1 d .
C12 C 0.29334(16) 0.76074(13) -0.10544(10) 0.0464(5) Uani 1 1 d .
C13 C 0.12186(15) 0.75562(13) 0.03254(9) 0.0450(5) Uani 1 1 d .
C14 C 0.23588(16) 0.87475(13) -0.03521(10) 0.0460(5) Uani 1 1 d .
C15 C 0.74452(15) 0.79266(12) -0.05039(9) 0.0451(5) Uani 1 1 d .
C16 C 0.58593(18) 0.87861(13) 0.10977(11) 0.0519(5) Uani 1 1 d .
O3 O 0.83564(15) 0.66739(10) -0.17761(8) 0.0785(5) Uani 1 1 d .
O1 O 0.33808(16) 0.65765(10) -0.17602(9) 0.0818(6) Uani 1 1 d .
C19 C 0.56928(16) 0.70435(12) 0.07469(10) 0.0467(5) Uani 1 1 d .
C20 C 0.79026(16) 0.76971(13) -0.10675(10) 0.0503(5) Uani 1 1 d .
C21 C 0.75021(17) 0.87991(13) -0.02789(10) 0.0479(5) Uani 1 1 d .
C22 C 0.28164(19) 0.67879(14) -0.12589(11) 0.0569(6) Uani 1 1 d .
C23 C 0.06928(16) 0.69826(12) 0.07588(10) 0.0459(5) Uani 1 1 d .
C24 C 0.15663(17) 0.64547(13) -0.05186(10) 0.0517(5) Uani 1 1 d .
C25 C 0.7518(2) 0.62455(15) -0.08464(12) 0.0671(7) Uani 1 1 d .
H25 H 0.7579 0.5686 -0.0961 0.080 Uiso 1 1 calc R
C26 C 0.84649(18) 0.81626(14) -0.15777(11) 0.0559(6) Uani 1 1 d .
C27 C 0.07958(17) 0.87266(13) 0.10611(10) 0.0498(5) Uani 1 1 d .
C28 C 0.59708(18) 0.67863(14) 0.13890(11) 0.0597(6) Uani 1 1 d .
H28 H 0.6613 0.6964 0.1619 0.072 Uiso 1 1 calc R
C29 C 0.36552(18) 0.80458(14) -0.14974(11) 0.0571(6) Uani 1 1 d .
C30 C 0.70430(18) 0.64489(14) -0.03021(12) 0.0589(6) Uani 1 1 d .
C31 C 0.79028(19) 0.68558(15) -0.12228(12) 0.0619(6) Uani 1 1 d .
C32 C 0.47187(18) 0.67871(14) 0.04299(12) 0.0640(6) Uani 1 1 d .
H32 H 0.4503 0.6967 0.0004 0.077 Uiso 1 1 calc R
C33 C -0.01166(19) 0.92122(15) 0.09434(12) 0.0644(6) Uani 1 1 d .
H33 H -0.0383 0.9356 0.0516 0.077 Uiso 1 1 calc R
C34 C -0.03934(17) 0.69926(15) 0.07722(12) 0.0644(6) Uani 1 1 d .
H34 H -0.0821 0.7338 0.0484 0.077 Uiso 1 1 calc R
C35 C -0.0252(2) 0.59771(17) 0.16266(13) 0.0758(8) Uani 1 1 d .
H35 H -0.0570 0.5637 0.1913 0.091 Uiso 1 1 calc R
C36 C 0.12974(19) 0.64634(15) 0.11969(12) 0.0643(6) Uani 1 1 d .
H36 H 0.2035 0.6453 0.1205 0.077 Uiso 1 1 calc R
C37 C 0.1204(2) 0.85458(16) 0.17017(11) 0.0677(7) Uani 1 1 d .
H37 H 0.1833 0.8241 0.1790 0.081 Uiso 1 1 calc R
C38 C 0.0769(2) 0.58275(15) -0.03296(14) 0.0801(8) Uani 1 1 d .
H38A H 0.0663 0.5396 -0.0656 0.120 Uiso 1 1 calc R
H38B H 0.0102 0.6104 -0.0297 0.120 Uiso 1 1 calc R
H38C H 0.1033 0.5582 0.0085 0.120 Uiso 1 1 calc R
C39 C 0.5308(2) 0.62706(16) 0.16902(12) 0.0750(7) Uani 1 1 d .
H39 H 0.5508 0.6100 0.2120 0.090 Uiso 1 1 calc R
C40 C 0.4353(2) 0.60070(17) 0.13589(14) 0.0763(8) Uani 1 1 d .
H40 H 0.3910 0.5652 0.1560 0.092 Uiso 1 1 calc R
C41 C 0.2989(2) 0.85723(19) -0.20073(12) 0.0850(8) Uani 1 1 d .
H41A H 0.2697 0.9041 -0.1799 0.127 Uiso 1 1 calc R
H41B H 0.2418 0.8239 -0.2225 0.127 Uiso 1 1 calc R
H41C H 0.3430 0.8771 -0.2322 0.127 Uiso 1 1 calc R
C42 C -0.0244(3) 0.92714(18) 0.20848(15) 0.0848(9) Uani 1 1 d .
H42 H -0.0609 0.9437 0.2428 0.102 Uiso 1 1 calc R
C43 C 0.46051(19) 0.85355(18) -0.11615(14) 0.0791(8) Uani 1 1 d .
H43A H 0.5115 0.8620 -0.1463 0.119 Uiso 1 1 calc R
H43B H 0.4933 0.8227 -0.0789 0.119 Uiso 1 1 calc R
H43C H 0.4367 0.9069 -0.1021 0.119 Uiso 1 1 calc R
C44 C 0.0831(2) 0.59617(16) 0.16215(13) 0.0763(8) Uani 1 1 d .
H44 H 0.1252 0.5610 0.1907 0.092 Uiso 1 1 calc R
C45 C 0.0676(3) 0.88184(19) 0.22105(13) 0.0844(8) Uani 1 1 d .
H45 H 0.0949 0.8692 0.2640 0.101 Uiso 1 1 calc R
C46 C 0.6374(2) 0.88908(16) 0.17249(12) 0.0718(7) Uani 1 1 d .
H46 H 0.7097 0.8768 0.1818 0.086 Uiso 1 1 calc R
C47 C 0.40610(19) 0.62708(16) 0.07321(14) 0.0733(7) Uani 1 1 d .
H47 H 0.3411 0.6100 0.0507 0.088 Uiso 1 1 calc R
C48 C 0.7863(2) 0.89068(19) -0.19114(12) 0.0818(8) Uani 1 1 d .
H48A H 0.7957 0.9387 -0.1629 0.123 Uiso 1 1 calc R
H48B H 0.7117 0.8774 -0.2000 0.123 Uiso 1 1 calc R
H48C H 0.8138 0.9028 -0.2315 0.123 Uiso 1 1 calc R
C49 C 0.4796(2) 0.89989(18) 0.09692(14) 0.0789(8) Uani 1 1 d .
H49 H 0.4444 0.8947 0.0546 0.095 Uiso 1 1 calc R
C50 C 0.4094(3) 0.72648(17) -0.18154(16) 0.0987(10) Uani 1 1 d .
H50A H 0.4150 0.7375 -0.2273 0.118 Uiso 1 1 calc R
H50B H 0.4799 0.7129 -0.1596 0.118 Uiso 1 1 calc R
C51 C -0.0857(2) 0.64978(17) 0.12057(15) 0.0773(8) Uani 1 1 d .
H51 H -0.1592 0.6520 0.1211 0.093 Uiso 1 1 calc R
C52 C -0.0634(2) 0.94839(17) 0.14542(16) 0.0805(8) Uani 1 1 d .
H52 H -0.1246 0.9811 0.1371 0.097 Uiso 1 1 calc R
C53 C 0.4748(3) 0.93646(17) 0.20824(17) 0.0922(10) Uani 1 1 d .
H53 H 0.4370 0.9543 0.2416 0.111 Uiso 1 1 calc R
C54 C 0.5812(3) 0.91784(18) 0.22152(13) 0.0902(9) Uani 1 1 d .
H54 H 0.6161 0.9246 0.2638 0.108 Uiso 1 1 calc R
C55 C 0.6706(3) 0.57141(15) 0.00924(14) 0.0886(9) Uani 1 1 d .
H55A H 0.7090 0.5222 -0.0008 0.133 Uiso 1 1 calc R
H55B H 0.5953 0.5620 -0.0016 0.133 Uiso 1 1 calc R
H55C H 0.6863 0.5836 0.0551 0.133 Uiso 1 1 calc R
C56 C 0.95942(19) 0.8405(2) -0.13026(14) 0.0854(9) Uani 1 1 d .
H56A H 0.9946 0.8652 -0.1642 0.128 Uiso 1 1 calc R
H56B H 0.9979 0.7915 -0.1137 0.128 Uiso 1 1 calc R
H56C H 0.9574 0.8801 -0.0954 0.128 Uiso 1 1 calc R
C57 C 0.8470(3) 0.74613(18) -0.20926(14) 0.0977(10) Uani 1 1 d .
H57A H 0.7885 0.7542 -0.2441 0.117 Uiso 1 1 calc R
H57B H 0.9135 0.7473 -0.2282 0.117 Uiso 1 1 calc R
C58 C 0.4247(3) 0.9288(2) 0.14607(18) 0.0972(10) Uani 1 1 d .
H58 H 0.3529 0.9431 0.1367 0.117 Uiso 1 1 calc R
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
C14 N1 C5 125.18(17)
C21 N2 C8 125.18(17)
C13 C5 N1 120.79(18)
C13 C5 C27 123.63(18)
N1 C5 C27 115.58(17)
C12 C6 C10 120.60(18)
C12 C6 C14 120.26(18)
C10 C6 C14 119.04(17)
C24 C7 C22 120.5(2)
C9 C8 N2 120.32(18)
C9 C8 C16 124.08(19)
N2 C8 C16 115.58(17)
C8 C9 C11 119.66(18)
C8 C9 C19 116.96(18)
C11 C9 C19 123.10(18)
C6 C10 C24 118.38(18)
C6 C10 C13 118.62(17)
C24 C10 C13 122.97(18)
C15 C11 C30 118.28(19)
C15 C11 C9 118.52(18)
C30 C11 C9 123.19(19)
C22 C12 C6 117.40(19)
C22 C12 C29 107.43(18)
C6 C12 C29 135.05(19)
C5 C13 C10 119.05(18)
C5 C13 C23 116.62(18)
C10 C13 C23 124.20(18)
O2 C14 N1 119.53(18)
O2 C14 C6 123.85(18)
N1 C14 C6 116.62(17)
C20 C15 C11 120.98(18)
C20 C15 C21 119.89(19)
C11 C15 C21 119.10(18)
C49 C16 C46 118.7(2)
C49 C16 C8 120.4(2)
C46 C16 C8 120.9(2)
C31 O3 C57 105.64(18)
C22 O1 C50 105.29(18)
C32 C19 C28 117.7(2)
C32 C19 C9 120.09(19)
C28 C19 C9 122.16(18)
C31 C20 C15 117.1(2)
C31 C20 C26 107.38(19)
C15 C20 C26 135.46(19)
O4 C21 N2 119.36(18)
O4 C21 C15 123.88(19)
N2 C21 C15 116.73(18)
O1 C22 C12 114.8(2)
O1 C22 C7 121.4(2)
C12 C22 C7 123.7(2)
C34 C23 C36 117.6(2)
C34 C23 C13 121.74(19)
C36 C23 C13 120.52(18)
C7 C24 C10 118.91(19)
C7 C24 C38 116.60(19)
C10 C24 C38 124.38(19)
C31 C25 C30 121.0(2)
C56 C26 C48 111.1(2)
C56 C26 C20 111.32(19)
C48 C26 C20 116.02(19)
C56 C26 C57 110.8(2)
C48 C26 C57 107.5(2)
C20 C26 C57 99.35(19)
C37 C27 C33 118.9(2)
C37 C27 C5 121.3(2)
C33 C27 C5 119.7(2)
C39 C28 C19 120.9(2)
C41 C29 C43 111.4(2)
C41 C29 C12 110.23(19)
C43 C29 C12 117.16(19)
C41 C29 C50 110.6(2)
C43 C29 C50 107.6(2)
C12 C29 C50 98.99(18)
C25 C30 C11 118.9(2)
C25 C30 C55 115.8(2)
C11 C30 C55 125.3(2)
O3 C31 C25 122.4(2)
O3 C31 C20 114.3(2)
C25 C31 C20 123.3(2)
C47 C32 C19 121.2(2)
C52 C33 C27 120.5(2)
C23 C34 C51 120.9(2)
C51 C35 C44 119.0(2)
C44 C36 C23 121.3(2)
C45 C37 C27 120.0(3)
C40 C39 C28 120.3(2)
C47 C40 C39 119.3(2)
C45 C42 C52 120.2(3)
C35 C44 C36 120.3(2)
C42 C45 C37 120.3(3)
C16 C46 C54 120.0(3)
C40 C47 C32 120.6(2)
C16 C49 C58 120.8(3)
O1 C50 C29 108.8(2)
C35 C51 C34 120.8(2)
C42 C52 C33 119.9(3)
C58 C53 C54 119.7(3)
C53 C54 C46 120.5(3)
O3 C57 C26 108.3(2)
C53 C58 C49 120.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C21 1.242(2)
N1 C14 1.360(2)
N1 C5 1.375(2)
N2 C21 1.357(2)
N2 C8 1.376(2)
O2 C14 1.240(2)
C5 C13 1.357(3)
C5 C27 1.485(3)
C6 C12 1.408(3)
C6 C10 1.435(3)
C6 C14 1.464(3)
C7 C24 1.376(3)
C7 C22 1.378(3)
C8 C9 1.359(3)
C8 C16 1.490(3)
C9 C11 1.456(3)
C9 C19 1.495(3)
C10 C24 1.439(3)
C10 C13 1.463(3)
C11 C15 1.432(3)
C11 C30 1.433(3)
C12 C22 1.376(3)
C12 C29 1.538(3)
C13 C23 1.493(3)
C15 C20 1.410(3)
C15 C21 1.467(3)
C16 C49 1.377(3)
C16 C46 1.380(3)
O3 C31 1.370(3)
O3 C57 1.432(3)
O1 C22 1.370(3)
O1 C50 1.434(3)
C19 C32 1.379(3)
C19 C28 1.386(3)
C20 C31 1.380(3)
C20 C26 1.534(3)
C23 C34 1.375(3)
C23 C36 1.381(3)
C24 C38 1.506(3)
C25 C31 1.372(3)
C25 C30 1.376(3)
C26 C56 1.515(3)
C26 C48 1.525(3)
C26 C57 1.543(3)
C27 C37 1.384(3)
C27 C33 1.384(3)
C28 C39 1.377(3)
C29 C41 1.513(3)
C29 C43 1.522(3)
C29 C50 1.544(3)
C30 C55 1.518(3)
C32 C47 1.374(3)
C33 C52 1.377(3)
C34 C51 1.378(3)
C35 C51 1.362(4)
C35 C44 1.369(4)
C36 C44 1.373(3)
C37 C45 1.382(3)
C39 C40 1.373(3)
C40 C47 1.363(4)
C42 C45 1.365(4)
C42 C52 1.371(4)
C46 C54 1.384(4)
C49 C58 1.378(4)
C53 C58 1.359(4)
C53 C54 1.368(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328867
