#------------------------------------------------------------------------------
#$Date: 2023-06-05 05:39:55 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284182 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/16/7131608.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_7131608
loop_
_publ_author_name
'Luo, Xian'
'Xu, Meng-Meng'
'Xu, Xiao-Ping'
'Ji, Shun-Jun'
_publ_section_title
;
 NBS-induced intramolecular annulation reactions for the divergent
 synthesis of fused- and spirocyclic indolines.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6576
_journal_page_last               6579
_journal_paper_doi               10.1039/d3cc01920a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C18 H15 F N2 O2'
_chemical_formula_sum            'C18 H15 F N2 O2'
_chemical_formula_weight         310.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.533(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1831(13)
_cell_length_b                   11.7646(14)
_cell_length_c                   12.1011(15)
_cell_measurement_reflns_used    4739
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.45
_cell_volume                     1547.9(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.448
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.7389.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0583
_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)+(0.0655P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1428
_reflns_number_total             3165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01920a2.cif
_cod_data_source_block           b220530a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7131607--7131608.cif.'
_cod_database_code               7131608
_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_max   0.995
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C12(H12), C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.55551(17) 0.36519(16) 0.48864(17) 0.0736(6) Uani 1 1 d . . . . .
O2 O 0.46144(15) 0.26496(16) 0.65992(15) 0.0688(6) Uani 1 1 d . . . . .
N2 N 0.39380(17) 0.31214(18) 0.55992(16) 0.0535(6) Uani 1 1 d . . . . .
F1 F 0.14890(19) 0.67503(16) 0.68810(17) 0.1125(7) Uani 1 1 d . . . . .
N1 N 0.12485(19) 0.2150(2) 0.62728(18) 0.0650(6) Uani 1 1 d . . . . .
C17 C 0.4458(3) 0.3553(2) 0.4800(2) 0.0545(7) Uani 1 1 d . . . . .
C8 C 0.2609(2) 0.3085(2) 0.5357(2) 0.0550(7) Uani 1 1 d . . . . .
C9 C 0.2019(2) 0.3939(2) 0.6012(2) 0.0576(7) Uani 1 1 d . . . . .
C10 C 0.1204(2) 0.3340(2) 0.6477(2) 0.0588(7) Uani 1 1 d . . . . .
C7 C 0.2047(2) 0.1983(2) 0.5681(2) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.2305(2) 0.0845(2) 0.5324(2) 0.0596(7) Uani 1 1 d . . . . .
C16 C 0.3415(2) 0.3873(2) 0.3828(2) 0.0664(8) Uani 1 1 d . . . . .
H16A H 0.356530 0.360377 0.311471 0.080 Uiso 1 1 calc R U . . .
H16B H 0.331237 0.469173 0.378614 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2293(2) 0.3313(2) 0.4063(2) 0.0656(8) Uani 1 1 d . . . . .
H15A H 0.211662 0.260650 0.364279 0.079 Uiso 1 1 calc R U . . .
H15B H 0.158367 0.380860 0.384956 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2143(3) 0.5083(3) 0.6129(2) 0.0691(8) Uani 1 1 d . . . . .
H14 H 0.269811 0.549178 0.582039 0.083 Uiso 1 1 calc R U . . .
C11 C 0.0453(2) 0.3879(3) 0.7068(2) 0.0719(8) Uani 1 1 d . . . . .
H11 H -0.011170 0.347063 0.736478 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1391(3) 0.5603(3) 0.6737(2) 0.0746(9) Uani 1 1 d . . . . .
C12 C 0.0564(3) 0.5044(3) 0.7208(2) 0.0768(9) Uani 1 1 d . . . . .
H12 H 0.008573 0.543726 0.761359 0.092 Uiso 1 1 calc R U . . .
C6 C 0.3225(3) 0.0611(3) 0.4754(3) 0.0759(8) Uani 1 1 d . . . . .
H6 H 0.371409 0.119999 0.459547 0.091 Uiso 1 1 calc R U . . .
C5 C 0.3421(3) -0.0473(3) 0.4423(3) 0.0831(9) Uani 1 1 d . . . . .
H5 H 0.403896 -0.061176 0.404261 0.100 Uiso 1 1 calc R U . . .
C2 C 0.1610(3) -0.0074(3) 0.5530(3) 0.0809(9) Uani 1 1 d . . . . .
H2 H 0.098953 0.004450 0.591141 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2725(4) -0.1342(3) 0.4646(3) 0.0898(10) Uani 1 1 d . . . . .
H4 H 0.287162 -0.207664 0.442658 0.108 Uiso 1 1 calc R U . . .
C18 C 0.5140(3) 0.3477(3) 0.7415(3) 0.0954(11) Uani 1 1 d . . . . .
H18A H 0.572558 0.392039 0.713413 0.143 Uiso 1 1 calc R U . . .
H18B H 0.554679 0.310672 0.810873 0.143 Uiso 1 1 calc R U . . .
H18C H 0.450475 0.396475 0.755805 0.143 Uiso 1 1 calc R U . . .
C3 C 0.1813(4) -0.1148(3) 0.5187(3) 0.0992(11) Uani 1 1 d . . . . .
H3 H 0.132479 -0.174609 0.532458 0.119 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'
F F 0.0171 0.0103 '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
N2 O2 C18 112.8(2) . . ?
O2 N2 C8 119.37(18) . . ?
C17 N2 O2 122.82(19) . . ?
C17 N2 C8 117.7(2) . . ?
C7 N1 C10 107.7(2) . . ?
O1 C17 N2 125.2(3) . . ?
O1 C17 C16 129.0(2) . . ?
N2 C17 C16 105.8(2) . . ?
N2 C8 C9 115.1(2) . . ?
N2 C8 C7 115.9(2) . . ?
N2 C8 C15 100.39(18) . . ?
C9 C8 C7 99.9(2) . . ?
C9 C8 C15 112.9(2) . . ?
C7 C8 C15 113.3(2) . . ?
C10 C9 C8 106.6(2) . . ?
C14 C9 C8 131.5(2) . . ?
C14 C9 C10 121.8(3) . . ?
C9 C10 N1 112.3(2) . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 N1 126.3(3) . . ?
N1 C7 C8 113.2(2) . . ?
N1 C7 C1 121.2(2) . . ?
C1 C7 C8 125.5(2) . . ?
C6 C1 C7 123.3(3) . . ?
C2 C1 C7 120.3(3) . . ?
C2 C1 C6 116.4(3) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C17 C16 C15 105.8(2) . . ?
H16A C16 H16B 108.7 . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C8 C15 H15A 110.7 . . ?
C8 C15 H15B 110.7 . . ?
C16 C15 C8 105.4(2) . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C9 C14 H14 122.1 . . ?
C9 C14 C13 115.8(3) . . ?
C13 C14 H14 122.1 . . ?
C10 C11 H11 120.9 . . ?
C10 C11 C12 118.1(3) . . ?
C12 C11 H11 120.9 . . ?
F1 C13 C14 117.8(3) . . ?
F1 C13 C12 117.8(3) . . ?
C12 C13 C14 124.4(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.8 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
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 C17 1.212(3) . ?
O2 N2 1.384(2) . ?
O2 C18 1.413(3) . ?
N2 C17 1.339(3) . ?
N2 C8 1.447(3) . ?
F1 C13 1.362(3) . ?
N1 C10 1.425(3) . ?
N1 C7 1.284(3) . ?
C17 C16 1.499(4) . ?
C8 C9 1.522(4) . ?
C8 C7 1.531(3) . ?
C8 C15 1.546(3) . ?
C9 C10 1.372(3) . ?
C9 C14 1.358(4) . ?
C10 C11 1.378(4) . ?
C7 C1 1.456(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.388(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C13 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(4) . ?
C13 C12 1.364(4) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.350(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.353(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 H3 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
O1 C17 C16 C15 166.8(3) . . . . ?
O2 N2 C17 O1 -5.3(4) . . . . ?
O2 N2 C17 C16 175.0(2) . . . . ?
O2 N2 C8 C9 76.5(3) . . . . ?
O2 N2 C8 C7 -39.5(3) . . . . ?
O2 N2 C8 C15 -162.0(2) . . . . ?
N2 C17 C16 C15 -13.5(3) . . . . ?
N2 C8 C9 C10 -130.2(2) . . . . ?
N2 C8 C9 C14 53.1(4) . . . . ?
N2 C8 C7 N1 129.5(2) . . . . ?
N2 C8 C7 C1 -53.8(3) . . . . ?
N2 C8 C15 C16 -20.8(3) . . . . ?
F1 C13 C12 C11 179.9(2) . . . . ?
N1 C10 C11 C12 178.2(2) . . . . ?
N1 C7 C1 C6 -175.1(2) . . . . ?
N1 C7 C1 C2 5.9(4) . . . . ?
C17 N2 C8 C9 -107.6(2) . . . . ?
C17 N2 C8 C7 136.3(2) . . . . ?
C17 N2 C8 C15 13.9(3) . . . . ?
C17 C16 C15 C8 21.6(3) . . . . ?
C8 N2 C17 O1 179.0(2) . . . . ?
C8 N2 C17 C16 -0.7(3) . . . . ?
C8 C9 C10 N1 4.4(3) . . . . ?
C8 C9 C10 C11 -175.8(2) . . . . ?
C8 C9 C14 C13 175.8(3) . . . . ?
C8 C7 C1 C6 8.5(4) . . . . ?
C8 C7 C1 C2 -170.5(2) . . . . ?
C9 C8 C7 N1 5.2(3) . . . . ?
C9 C8 C7 C1 -178.2(2) . . . . ?
C9 C8 C15 C16 102.3(2) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C9 C14 C13 F1 179.7(2) . . . . ?
C9 C14 C13 C12 0.1(4) . . . . ?
C10 N1 C7 C8 -2.8(3) . . . . ?
C10 N1 C7 C1 -179.7(2) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C7 N1 C10 C9 -1.1(3) . . . . ?
C7 N1 C10 C11 179.1(3) . . . . ?
C7 C8 C9 C10 -5.4(2) . . . . ?
C7 C8 C9 C14 178.0(3) . . . . ?
C7 C8 C15 C16 -145.1(2) . . . . ?
C7 C1 C6 C5 -179.1(3) . . . . ?
C7 C1 C2 C3 178.7(3) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C15 C8 C9 C10 115.3(2) . . . . ?
C15 C8 C9 C14 -61.4(4) . . . . ?
C15 C8 C7 N1 -115.2(2) . . . . ?
C15 C8 C7 C1 61.5(3) . . . . ?
C14 C9 C10 N1 -178.6(2) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C14 C13 C12 C11 -0.5(5) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C18 O2 N2 C17 79.1(3) . . . . ?
C18 O2 N2 C8 -105.3(3) . . . . ?
