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#$Date: 2022-07-08 10:10:17 +0300 (Fri, 08 Jul 2022) $
#$Revision: 276736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105665.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_8105665
loop_
_publ_author_name
'Bai, Yunli'
'Wang, Yanhong'
'Li, Xingyi'
'Xun, Miao-Miao'
'Yuan, Changchun'
_publ_section_title
;
 Crystal structure of
 rac-3,6-dimethyl-5-(prop-1-en-2-yl)-6-vinyl-1,4,5,6-tetrahydro-2H-indol-2-one,
 C15H19NO
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              419
_journal_page_last               420
_journal_paper_doi               10.1515/ncrs-2018-0425
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                97.879(4)
_cell_angle_beta                 93.543(5)
_cell_angle_gamma                116.785(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9535(5)
_cell_length_b                   7.4037(6)
_cell_length_c                   14.5179(9)
_cell_measurement_reflns_used    4028
_cell_measurement_temperature    173
_cell_measurement_theta_max      66.218
_cell_measurement_theta_min      3.104
_cell_volume                     654.43(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9746
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        63.638
_diffrn_reflns_theta_max         63.638
_diffrn_reflns_theta_min         3.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.1254 before and 0.0632 after correction. The 
Ratio of minimum to maximum transmission is 0.7654. The λ/2 
correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0520
_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)+(0.0787P)²+0.2534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1768
_reflns_number_total             2069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0425_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105665
_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   0.936
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C14(H14)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.6563(3) 0.2502(2) 0.59104(10) 0.0403(4) Uani 1 1 d . . . . .
N1 N 0.5548(3) 0.1902(2) 0.43052(12) 0.0345(5) Uani 1 1 d . . . . .
H1 H 0.4728 0.0559 0.4208 0.041 Uiso 1 1 calc R . . . .
C2 C 0.7725(3) 0.5273(3) 0.50022(14) 0.0305(5) Uani 1 1 d . . . . .
C1 C 0.6576(3) 0.3111(3) 0.51614(14) 0.0317(5) Uani 1 1 d . . . . .
C3 C 0.7387(3) 0.5225(3) 0.40802(14) 0.0301(5) Uani 1 1 d . . . . .
C7 C 0.5897(3) 0.4090(3) 0.20427(14) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.8984(4) 0.7053(3) 0.57884(15) 0.0381(5) Uani 1 1 d . . . . .
H4A H 0.7985 0.7456 0.6096 0.057 Uiso 1 1 calc GR . . . .
H4B H 1.0044 0.8215 0.5540 0.057 Uiso 1 1 calc GR . . . .
H4C H 0.9748 0.6655 0.6245 0.057 Uiso 1 1 calc GR . . . .
C9 C 0.8114(3) 0.6876(3) 0.35023(14) 0.0344(5) Uani 1 1 d . . . . .
H9A H 0.9591 0.7970 0.3776 0.041 Uiso 1 1 calc R . . . .
H9B H 0.7118 0.7499 0.3511 0.041 Uiso 1 1 calc R . . . .
C8 C 0.8141(3) 0.5995(3) 0.24824(14) 0.0328(5) Uani 1 1 d . . . . .
H8 H 0.9227 0.5460 0.2511 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5272(3) 0.2536(3) 0.26954(15) 0.0348(5) Uani 1 1 d . . . . .
H6 H 0.4345 0.1123 0.2442 0.042 Uiso 1 1 calc R . . . .
C13 C 0.4078(4) 0.4691(3) 0.19024(16) 0.0408(6) Uani 1 1 d . . . . .
H13A H 0.3955 0.5388 0.2503 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.2699 0.3451 0.1665 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.4416 0.5620 0.1449 0.061 Uiso 1 1 calc GR . . . .
C5 C 0.5983(3) 0.3099(3) 0.36066(14) 0.0311(5) Uani 1 1 d . . . . .
C14 C 0.6172(4) 0.3029(3) 0.11268(15) 0.0404(6) Uani 1 1 d . . . . .
H14 H 0.7327 0.2676 0.1154 0.048 Uiso 1 1 calc R . . . .
C10 C 0.8959(3) 0.7649(3) 0.18803(15) 0.0397(6) Uani 1 1 d . . . . .
C11 C 0.8490(4) 0.9225(4) 0.19745(18) 0.0534(7) Uani 1 1 d . . . . .
H11A H 0.9075 1.0251 0.1599 0.064 Uiso 1 1 calc R . . . .
H11B H 0.7572 0.9318 0.2417 0.064 Uiso 1 1 calc R . . . .
C15 C 0.5008(5) 0.2542(4) 0.03036(17) 0.0536(7) Uani 1 1 d . . . . .
H15A H 0.3831 0.2856 0.0232 0.064 Uiso 1 1 calc R . . . .
H15B H 0.5341 0.1875 -0.0223 0.064 Uiso 1 1 calc R . . . .
C12 C 1.0387(5) 0.7477(4) 0.1194(2) 0.0636(8) Uani 1 1 d . . . . .
H12A H 1.1599 0.7368 0.1517 0.095 Uiso 1 1 calc GR . . . .
H12B H 1.0959 0.8702 0.0902 0.095 Uiso 1 1 calc GR . . . .
H12C H 0.9549 0.6249 0.0708 0.095 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 H1 124.8 . .
C1 N1 C5 110.39(16) . .
C5 N1 H1 124.8 . .
C1 C2 C4 122.17(18) . .
C3 C2 C1 107.57(17) . .
C3 C2 C4 130.26(19) . .
O1 C1 N1 125.90(19) . .
O1 C1 C2 127.48(19) . .
N1 C1 C2 106.62(17) . .
C2 C3 C9 132.46(18) . .
C2 C3 C5 109.12(18) . .
C5 C3 C9 118.41(18) . .
C6 C7 C8 108.72(16) . .
C6 C7 C13 108.69(17) . .
C13 C7 C8 112.31(16) . .
C14 C7 C8 109.08(16) . .
C14 C7 C6 106.36(16) . .
C14 C7 C13 111.47(18) . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C9 H9A 109.5 . .
C3 C9 H9B 109.5 . .
C3 C9 C8 110.73(16) . .
H9A C9 H9B 108.1 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C7 C8 H8 106.1 . .
C9 C8 C7 111.92(16) . .
C9 C8 H8 106.1 . .
C10 C8 C7 113.58(17) . .
C10 C8 C9 112.26(16) . .
C10 C8 H8 106.1 . .
C7 C6 H6 119.1 . .
C5 C6 C7 121.77(18) . .
C5 C6 H6 119.1 . .
C7 C13 H13A 109.5 . .
C7 C13 H13B 109.5 . .
C7 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N1 C5 C3 106.27(17) . .
C6 C5 N1 129.46(18) . .
C6 C5 C3 124.24(19) . .
C7 C14 H14 116.1 . .
C15 C14 C7 127.7(2) . .
C15 C14 H14 116.1 . .
C11 C10 C8 122.7(2) . .
C11 C10 C12 120.8(2) . .
C12 C10 C8 116.5(2) . .
C10 C11 H11A 120.0 . .
C10 C11 H11B 120.0 . .
H11A C11 H11B 120.0 . .
C14 C15 H15A 120.0 . .
C14 C15 H15B 120.0 . .
H15A C15 H15B 120.0 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.232(2) .
N1 H1 0.8800 .
N1 C1 1.366(3) .
N1 C5 1.396(3) .
C2 C1 1.492(3) .
C2 C3 1.337(3) .
C2 C4 1.493(3) .
C3 C9 1.493(3) .
C3 C5 1.462(3) .
C7 C8 1.574(3) .
C7 C6 1.519(3) .
C7 C13 1.530(3) .
C7 C14 1.517(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C8 1.539(3) .
C8 H8 1.0000 .
C8 C10 1.522(3) .
C6 H6 0.9500 .
C6 C5 1.323(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14 0.9500 .
C14 C15 1.309(3) .
C10 C11 1.338(3) .
C10 C12 1.483(3) .
C11 H11A 0.9500 .
C11 H11B 0.9500 .
C15 H15A 0.9500 .
C15 H15B 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
