#------------------------------------------------------------------------------
#$Date: 2025-07-06 15:12:50 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300463 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/44/7134498.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_7134498
loop_
_publ_author_name
'Gowda, Punith S.'
'Sharada, Duddu S.'
'Satyanarayana, Gedu'
_publ_section_title
;
 A TBADT-enabled photo-induced radical cyclization pathway: concise access
 to functionalized oxindoles
;
_journal_issue                   46
_journal_name_full               'Chemical Communications'
_journal_page_first              8391
_journal_page_last               8394
_journal_paper_doi               10.1039/D5CC01590A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H21 N O'
_chemical_formula_sum            'C16 H21 N O'
_chemical_formula_weight         243.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-23
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-12 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.577(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.461(3)
_cell_length_b                   7.0742(11)
_cell_length_c                   10.8476(15)
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.695
_cell_measurement_theta_min      2.153
_cell_volume                     1451.7(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16148
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.089
_diffrn_reflns_theta_min         2.533
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.7038.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0530
_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)+(0.0666P)²+0.4089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1035
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc01590a2.cif
_cod_data_source_block           mo_gs_ps_p4_141
_cod_depositor_comments
'Adding full bibliography for 7134498--7134500.cif.'
_cod_database_code               7134498
_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.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H16A(0.5) H16B(0.5) H16C(0.5) H2A(0.5) H2B(0.5) H2C(0.5) H1A(0.5)
 H1B(0.5) H1C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C3(H3)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O001 O 0.92999(9) 0.500000 0.84440(18) 0.0756(7) Uani 1 2 d S T P . .
N002 N 0.84541(9) 0.500000 0.95969(17) 0.0499(6) Uani 1 2 d S T P . .
C10 C 0.80279(11) 0.500000 0.7423(2) 0.0454(6) Uani 1 2 d S T P . .
C7 C 0.74348(11) 0.500000 0.8045(2) 0.0453(6) Uani 1 2 d S T P . .
C8 C 0.77153(11) 0.500000 0.9343(2) 0.0451(6) Uani 1 2 d S T P . .
C9 C 0.86779(12) 0.500000 0.8488(2) 0.0510(6) Uani 1 2 d S T P . .
C6 C 0.67087(12) 0.500000 0.7590(2) 0.0537(7) Uani 1 2 d S T P . .
H6 H 0.651659 0.500000 0.671974 0.064 Uiso 1 2 calc R U P . .
C11 C 0.79790(12) 0.500000 0.6172(2) 0.0507(6) Uani 1 2 d S T P . .
H11 H 0.751682 0.500000 0.568539 0.061 Uiso 1 2 calc R U P . .
C3 C 0.72877(13) 0.500000 1.0194(2) 0.0551(7) Uani 1 2 d S T P . .
H3 H 0.748482 0.500000 1.106258 0.066 Uiso 1 2 calc R U P . .
C4 C 0.65539(13) 0.500000 0.9731(3) 0.0570(7) Uani 1 2 d S T P . .
C5 C 0.62627(13) 0.500000 0.8425(3) 0.0570(7) Uani 1 2 d S T P . .
C12 C 0.85313(13) 0.500000 0.5401(2) 0.0589(7) Uani 1 2 d S T P . .
C16 C 0.89201(14) 0.500000 1.0847(2) 0.0631(8) Uani 1 2 d S T P . .
H16A H 0.878020 0.598111 1.134862 0.095 Uiso 0.5 1 calc R U P A -1
H16B H 0.939659 0.522063 1.077931 0.095 Uiso 0.5 1 calc R U P A -1
H16C H 0.889337 0.379826 1.124410 0.095 Uiso 0.5 1 calc R U P A -1
C13 C 0.8144(2) 0.500000 0.3992(3) 0.0818(10) Uani 1 2 d S T P . .
C15 C 0.89832(15) 0.6783(5) 0.5675(3) 0.0880(9) Uani 1 1 d . . . . .
C2 C 0.54748(13) 0.500000 0.7889(3) 0.0821(10) Uani 1 2 d S T P . .
H2A H 0.537553 0.467420 0.700553 0.123 Uiso 0.5 1 calc R U P B -1
H2B H 0.528894 0.623440 0.798419 0.123 Uiso 0.5 1 calc R U P B -1
H2C H 0.525789 0.409141 0.833512 0.123 Uiso 0.5 1 calc R U P B -1
C1 C 0.60928(16) 0.500000 1.0669(3) 0.0827(10) Uani 1 2 d S T P . .
H1A H 0.637987 0.479852 1.150728 0.124 Uiso 0.5 1 calc R U P C -1
H1B H 0.574904 0.400654 1.045959 0.124 Uiso 0.5 1 calc R U P C -1
H1C H 0.585541 0.619493 1.063624 0.124 Uiso 0.5 1 calc R U P C -1
H13A H 0.8527(17) 0.500000 0.348(3) 0.098(10) Uiso 1 2 d S . P . .
H15A H 0.9267(12) 0.677(3) 0.655(2) 0.105(8) Uiso 1 1 d . . . . .
H13B H 0.7790(12) 0.618(4) 0.375(2) 0.114(8) Uiso 1 1 d . . . . .
H15B H 0.9309(13) 0.682(4) 0.513(2) 0.123(9) Uiso 1 1 d . . . . .
H15C H 0.8657(14) 0.803(4) 0.553(3) 0.132(11) 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
C8 N002 C16 125.1(2) . . ?
C9 N002 C8 110.54(19) . . ?
C9 N002 C16 124.4(2) . . ?
C7 C10 C9 104.91(19) . . ?
C11 C10 C7 126.2(2) . . ?
C11 C10 C9 128.9(2) . . ?
C8 C7 C10 107.64(19) . . ?
C6 C7 C10 133.1(2) . . ?
C6 C7 C8 119.3(2) . . ?
C7 C8 N002 109.95(19) . . ?
C3 C8 N002 128.4(2) . . ?
C3 C8 C7 121.6(2) . . ?
O001 C9 N002 123.7(2) . . ?
O001 C9 C10 129.3(2) . . ?
N002 C9 C10 106.96(19) . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C10 C11 H11 113.9 . . ?
C10 C11 C12 132.2(2) . . ?
C12 C11 H11 113.9 . . ?
C8 C3 H3 120.5 . . ?
C8 C3 C4 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C1 118.6(3) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 C1 121.4(3) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C2 118.8(3) . . ?
C4 C5 C2 121.7(2) . . ?
C11 C12 C13 107.7(2) . . ?
C11 C12 C15 110.15(16) . 6_565 ?
C11 C12 C15 110.15(15) . . ?
C15 C12 C13 108.65(17) . . ?
C15 C12 C13 108.65(17) 6_565 . ?
C15 C12 C15 111.4(3) . 6_565 ?
N002 C16 H16A 109.5 . . ?
N002 C16 H16B 109.5 . . ?
N002 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13A 106.6(18) . . ?
C12 C13 H13B 112.1(13) . . ?
H13A C13 H13B 112.0(16) . . ?
C12 C15 H15A 110.4(14) . . ?
C12 C15 H15B 109.6(16) . . ?
C12 C15 H15C 110.8(14) . . ?
H15A C15 H15B 107(2) . . ?
H15A C15 H15C 109(2) . . ?
H15B C15 H15C 110(2) . . ?
C5 C2 H2A 109.5 . . ?
C5 C2 H2B 109.5 . . ?
C5 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
O001 C9 1.223(3) . ?
N002 C8 1.399(3) . ?
N002 C9 1.372(3) . ?
N002 C16 1.443(3) . ?
C10 C7 1.468(3) . ?
C10 C9 1.500(3) . ?
C10 C11 1.337(3) . ?
C7 C8 1.386(3) . ?
C7 C6 1.383(3) . ?
C8 C3 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.394(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.509(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.397(4) . ?
C4 C1 1.506(4) . ?
C5 C2 1.507(4) . ?
C12 C13 1.537(4) . ?
C12 C15 1.526(3) 6_565 ?
C12 C15 1.526(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13A 1.03(3) . ?
C13 H13B 1.07(2) . ?
C15 H15A 0.98(2) . ?
C15 H15B 0.96(2) . ?
C15 H15C 1.08(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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
N002 C8 C3 C4 180.000(1) . . . . ?
C10 C7 C8 N002 0.000(1) . . . . ?
C10 C7 C8 C3 180.000(1) . . . . ?
C10 C7 C6 C5 180.000(1) . . . . ?
C10 C11 C12 C13 180.000(1) . . . . ?
C10 C11 C12 C15 61.67(18) . . . 6_565 ?
C10 C11 C12 C15 -61.67(18) . . . . ?
C7 C10 C9 O001 180.000(1) . . . . ?
C7 C10 C9 N002 0.000(1) . . . . ?
C7 C10 C11 C12 180.000(1) . . . . ?
C7 C8 C3 C4 0.000(1) . . . . ?
C7 C6 C5 C4 0.000(1) . . . . ?
C7 C6 C5 C2 180.000(1) . . . . ?
C8 N002 C9 O001 180.000(1) . . . . ?
C8 N002 C9 C10 0.000(1) . . . . ?
C8 C7 C6 C5 0.000(1) . . . . ?
C8 C3 C4 C5 0.000(1) . . . . ?
C8 C3 C4 C1 180.000(1) . . . . ?
C9 N002 C8 C7 0.000(1) . . . . ?
C9 N002 C8 C3 180.000(1) . . . . ?
C9 C10 C7 C8 0.000(1) . . . . ?
C9 C10 C7 C6 180.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C6 C7 C8 N002 180.000(1) . . . . ?
C6 C7 C8 C3 0.000(1) . . . . ?
C11 C10 C7 C8 180.000(1) . . . . ?
C11 C10 C7 C6 0.000(1) . . . . ?
C11 C10 C9 O001 0.000(1) . . . . ?
C11 C10 C9 N002 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C5 C2 180.000(1) . . . . ?
C16 N002 C8 C7 180.000(1) . . . . ?
C16 N002 C8 C3 0.000(1) . . . . ?
C16 N002 C9 O001 0.000(1) . . . . ?
C16 N002 C9 C10 180.000(1) . . . . ?
C1 C4 C5 C6 180.000(1) . . . . ?
C1 C4 C5 C2 0.000(1) . . . . ?
