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#$Date: 2023-02-20 15:31:21 +0200 (Mon, 20 Feb 2023) $
#$Revision: 281042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246293.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_7246293
loop_
_publ_author_name
'Reddy, Yeruva Pavankumar'
'Srinivasadesikan, V.'
'Balamurugan, Rengarajan'
'Lin, M. C.'
'Anwar, Shaik'
_publ_section_title
;
 Synthesis of tetrahydrochromenes and dihydronaphthofurans via a cascade
 process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight
 for 6-endo-trig and 5-exo-trig cyclisation
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              5796
_journal_page_last               5803
_journal_paper_doi               10.1039/D2RA08163F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0111(10)
_cell_length_b                   11.7592(12)
_cell_length_c                   13.0970(15)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.783
_cell_measurement_theta_min      2.327
_cell_volume                     1541.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28119
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.328
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6725
_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    1.324
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_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)+(0.0528P)²+0.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3158
_reflns_number_total             3504
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra08163f2.cif
_cod_data_source_block           KB100_0m
_cod_database_code               7246293
_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   0.970
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'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
O1 O 0.85416(19) 0.39417(13) 0.42643(16) 0.0542(4) Uani 1 1 d . . . . .
O2 O 1.0303(3) 0.5631(2) 0.64790(18) 0.0946(8) Uani 1 1 d . . . . .
O3 O 1.0937(4) 0.4285(2) 0.5552(3) 0.1292(14) Uani 1 1 d . . . . .
N1 N 1.0351(2) 0.51519(16) 0.56690(18) 0.0521(5) Uani 1 1 d . . . . .
C1 C 0.3995(3) 0.4974(3) 0.6540(2) 0.0640(8) Uani 1 1 d . . . . .
H1 H 0.327976 0.446936 0.652988 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3928(3) 0.5918(3) 0.7151(3) 0.0689(8) Uani 1 1 d . . . . .
H2 H 0.317649 0.604564 0.755211 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4978(3) 0.6678(3) 0.7170(2) 0.0632(7) Uani 1 1 d . . . . .
H3 H 0.493797 0.731807 0.758568 0.076 Uiso 1 1 calc R U . . .
C4 C 0.6092(2) 0.6484(2) 0.65658(19) 0.0493(5) Uani 1 1 d . . . . .
H4 H 0.679329 0.700279 0.657743 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6183(2) 0.55280(18) 0.59421(17) 0.0400(4) Uani 1 1 d . . . . .
C6 C 0.5099(2) 0.4753(2) 0.5936(2) 0.0491(6) Uani 1 1 d . . . . .
C7 C 0.5163(3) 0.3749(2) 0.5232(2) 0.0608(7) Uani 1 1 d . . . . .
H7A H 0.480897 0.396547 0.457091 0.073 Uiso 1 1 calc R U . . .
H7B H 0.460340 0.314621 0.550191 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6571(3) 0.32998(19) 0.5095(2) 0.0557(6) Uani 1 1 d . . . . .
H8A H 0.685197 0.290670 0.571017 0.067 Uiso 1 1 calc R U . . .
H8B H 0.659278 0.276203 0.453398 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7508(2) 0.42680(17) 0.48788(18) 0.0430(5) Uani 1 1 d . . . . .
C10 C 0.7340(2) 0.53064(16) 0.52829(15) 0.0364(4) Uani 1 1 d . . . . .
C11 C 0.83452(19) 0.62410(15) 0.50889(16) 0.0345(4) Uani 1 1 d . . . . .
H11 H 0.850011 0.664340 0.573343 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9665(2) 0.56988(18) 0.47536(18) 0.0409(5) Uani 1 1 d . . . . .
H12 H 1.024827 0.629418 0.447909 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9443(3) 0.4814(2) 0.3940(2) 0.0513(6) Uani 1 1 d . . . . .
H13A H 0.908697 0.517859 0.333356 0.062 Uiso 1 1 calc R U . . .
H13B H 1.029297 0.447237 0.376016 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7896(2) 0.71112(16) 0.42915(16) 0.0347(4) Uani 1 1 d . . . . .
C15 C 0.6914(2) 0.68731(18) 0.35799(18) 0.0447(5) Uani 1 1 d . . . . .
H15 H 0.649259 0.616833 0.358885 0.054 Uiso 1 1 calc R U . . .
C16 C 0.6550(3) 0.7675(2) 0.28518(19) 0.0542(6) Uani 1 1 d . . . . .
H16 H 0.588855 0.750245 0.237757 0.065 Uiso 1 1 calc R U . . .
C17 C 0.7162(3) 0.8723(2) 0.2829(2) 0.0542(6) Uani 1 1 d . . . . .
H17 H 0.692935 0.925395 0.233379 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8116(3) 0.8975(2) 0.3540(3) 0.0580(6) Uani 1 1 d . . . . .
H18 H 0.852357 0.968527 0.353446 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8479(2) 0.81826(18) 0.4268(2) 0.0480(5) Uani 1 1 d . . . . .
H19 H 0.912517 0.836969 0.475026 0.058 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'
O O 0.0106 0.0060 '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'
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
C9 O1 C13 116.84(17) . . ?
O3 N1 O2 122.4(3) . . ?
O3 N1 C12 119.0(3) . . ?
O2 N1 C12 118.60(19) . . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 C10 122.64(19) . . ?
C6 C5 C10 119.1(2) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C7 118.5(2) . . ?
C6 C7 C8 112.8(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 109.8(2) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 O1 125.67(19) . . ?
C10 C9 C8 122.5(2) . . ?
O1 C9 C8 111.80(19) . . ?
C9 C10 C5 119.50(19) . . ?
C9 C10 C11 120.80(19) . . ?
C5 C10 C11 119.68(16) . . ?
C10 C11 C14 113.90(17) . . ?
C10 C11 C12 108.66(16) . . ?
C14 C11 C12 109.66(17) . . ?
C10 C11 H11 108.2 . . ?
C14 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C13 C12 N1 109.38(19) . . ?
C13 C12 C11 111.30(18) . . ?
N1 C12 C11 109.79(19) . . ?
C13 C12 H12 108.8 . . ?
N1 C12 H12 108.8 . . ?
C11 C12 H12 108.8 . . ?
O1 C13 C12 112.2(2) . . ?
O1 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 117.9(2) . . ?
C15 C14 C11 122.25(17) . . ?
C19 C14 C11 119.86(19) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
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
O1 C9 1.366(3) . ?
O1 C13 1.431(3) . ?
O2 N1 1.202(3) . ?
O3 N1 1.186(3) . ?
N1 C12 1.524(3) . ?
C1 C2 1.370(5) . ?
C1 C6 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(3) . ?
C5 C10 1.468(3) . ?
C6 C7 1.500(4) . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.502(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.341(3) . ?
C10 C11 1.512(3) . ?
C11 C14 1.530(3) . ?
C11 C12 1.531(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.506(3) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.383(3) . ?
C14 C19 1.389(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
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
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C10 179.1(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C10 C5 C6 C1 -178.5(2) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
C1 C6 C7 C8 -149.1(2) . . . . ?
C5 C6 C7 C8 34.0(3) . . . . ?
C6 C7 C8 C9 -47.6(3) . . . . ?
C13 O1 C9 C10 -6.9(3) . . . . ?
C13 O1 C9 C8 175.2(2) . . . . ?
C7 C8 C9 C10 33.4(3) . . . . ?
C7 C8 C9 O1 -148.7(2) . . . . ?
O1 C9 C10 C5 -179.3(2) . . . . ?
C8 C9 C10 C5 -1.7(3) . . . . ?
O1 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 176.8(2) . . . . ?
C4 C5 C10 C9 165.3(2) . . . . ?
C6 C5 C10 C9 -15.8(3) . . . . ?
C4 C5 C10 C11 -13.2(3) . . . . ?
C6 C5 C10 C11 165.70(19) . . . . ?
C9 C10 C11 C14 102.4(2) . . . . ?
C5 C10 C11 C14 -79.1(2) . . . . ?
C9 C10 C11 C12 -20.1(3) . . . . ?
C5 C10 C11 C12 158.33(18) . . . . ?
O3 N1 C12 C13 20.6(4) . . . . ?
O2 N1 C12 C13 -161.2(3) . . . . ?
O3 N1 C12 C11 143.0(3) . . . . ?
O2 N1 C12 C11 -38.7(3) . . . . ?
C10 C11 C12 C13 47.4(2) . . . . ?
C14 C11 C12 C13 -77.7(2) . . . . ?
C10 C11 C12 N1 -73.9(2) . . . . ?
C14 C11 C12 N1 161.04(16) . . . . ?
C9 O1 C13 C12 35.8(3) . . . . ?
N1 C12 C13 O1 64.4(3) . . . . ?
C11 C12 C13 O1 -57.1(3) . . . . ?
C10 C11 C14 C15 -20.7(3) . . . . ?
C12 C11 C14 C15 101.3(2) . . . . ?
C10 C11 C14 C19 159.2(2) . . . . ?
C12 C11 C14 C19 -78.8(2) . . . . ?
C19 C14 C15 C16 1.5(3) . . . . ?
C11 C14 C15 C16 -178.6(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C15 C14 C19 C18 -1.7(4) . . . . ?
C11 C14 C19 C18 178.4(2) . . . . ?
