#------------------------------------------------------------------------------
#$Date: 2020-04-07 02:28:49 +0300 (Tue, 07 Apr 2020) $
#$Revision: 250425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038200.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_4038200
loop_
_publ_author_name
'Rahman, Md Mahbubur'
'Liu, Chengwei'
'Bisz, Elwira'
'Dziuk, Błażej'
'Lalancette, Roger A.'
'Wang, Qi'
'Chen, Hao'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 N-Acyl-Glutarimides: Effect of Glutarimide Ring on the Structures of
 Fully Perpendicular Twisted Amides and N-C Bond Cross-Coupling.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00227
_journal_year                    2020
_chemical_formula_sum            'C19 H11 N O3'
_chemical_formula_weight         301.29
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.524(5)
_cell_angle_beta                 79.007(6)
_cell_angle_gamma                69.240(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2903(5)
_cell_length_b                   9.2896(5)
_cell_length_c                   11.4353(7)
_cell_measurement_reflns_used    4802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.994
_cell_measurement_theta_min      3.012
_cell_volume                     701.52(8)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4802
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99542
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0361
_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)+(0.0485P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1700
_reflns_number_total             2705
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00227_si_002.cif
_cod_data_source_block           BD362_a
_cod_database_code               4038200
_shelx_shelxl_version_number     2014/7
_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.
;
_exptl_absorpt_special_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
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 0.72674(15) 0.43892(11) 0.43532(9) 0.0567(3) Uani 1 1 d . . . . .
N1 N 0.83649(16) 0.29294(12) 0.28668(10) 0.0411(3) Uani 1 1 d . . . . .
C1 C 0.75908(19) 0.31318(15) 0.40648(12) 0.0409(3) Uani 1 1 d . . . . .
C2 C 0.72503(18) 0.17651(14) 0.48676(12) 0.0380(3) Uani 1 1 d . . . . .
O2 O 0.95909(15) 0.15610(11) 0.13269(9) 0.0581(3) Uani 1 1 d . . . . .
O3 O 1.04319(15) 0.43511(11) 0.20082(10) 0.0587(3) Uani 1 1 d . . . . .
C3 C 0.78082(17) 0.03308(14) 0.44344(12) 0.0373(3) Uani 1 1 d . . . . .
C4 C 0.86253(18) 0.01994(14) 0.32242(12) 0.0398(3) Uani 1 1 d . . . . .
C5 C 0.89189(19) 0.15567(15) 0.23851(13) 0.0413(3) Uani 1 1 d . . . . .
C8 C 0.6708(2) -0.08279(18) 0.64390(14) 0.0548(4) Uani 1 1 d . . . . .
H8 H 0.6541 -0.1690 0.6979 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6147(2) 0.05697(19) 0.68232(14) 0.0572(4) Uani 1 1 d . . . . .
H7 H 0.5575 0.0658 0.7615 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6423(2) 0.18741(17) 0.60362(13) 0.0497(4) Uani 1 1 d . . . . .
H6 H 0.6041 0.2823 0.6310 0.060 Uiso 1 1 calc R U . . .
C9 C 0.75413(19) -0.09946(15) 0.52347(14) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.8127(2) -0.24173(17) 0.47907(16) 0.0585(4) Uani 1 1 d . . . . .
H10 H 0.7967 -0.3299 0.5306 0.070 Uiso 1 1 calc R U . . .
C11 C 0.8920(2) -0.25192(17) 0.36258(18) 0.0634(5) Uani 1 1 d . . . . .
H11 H 0.9304 -0.3469 0.3352 0.076 Uiso 1 1 calc R U . . .
C12 C 0.9164(2) -0.12089(17) 0.28342(15) 0.0552(4) Uani 1 1 d . . . . .
H12 H 0.9696 -0.1290 0.2035 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8812(2) 0.42727(15) 0.20766(12) 0.0430(3) Uani 1 1 d . . . . .
C14 C 0.71865(19) 0.54242(14) 0.14530(11) 0.0405(3) Uani 1 1 d . . . . .
C15 C 0.5309(2) 0.53036(17) 0.16095(13) 0.0506(4) Uani 1 1 d . . . . .
H15 H 0.5042 0.4458 0.2123 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3843(2) 0.6431(2) 0.10074(15) 0.0625(4) Uani 1 1 d . . . . .
H16 H 0.2585 0.6348 0.1116 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4232(3) 0.7683(2) 0.02432(15) 0.0676(5) Uani 1 1 d . . . . .
H17 H 0.3234 0.8449 -0.0157 0.081 Uiso 1 1 calc R U . . .
C18 C 0.6094(3) 0.77990(18) 0.00729(14) 0.0639(5) Uani 1 1 d . . . . .
H18 H 0.6359 0.8638 -0.0451 0.077 Uiso 1 1 calc R U . . .
C19 C 0.7566(2) 0.66803(16) 0.06733(12) 0.0512(4) Uani 1 1 d . . . . .
H19 H 0.8824 0.6766 0.0556 0.061 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
C5 N1 C1 126.87(11) . . ?
C5 N1 C13 117.04(11) . . ?
C1 N1 C13 115.81(10) . . ?
O1 C1 N1 118.68(12) . . ?
O1 C1 C2 125.57(13) . . ?
N1 C1 C2 115.75(11) . . ?
C6 C2 C3 120.30(13) . . ?
C6 C2 C1 119.78(12) . . ?
C3 C2 C1 119.91(12) . . ?
C4 C3 C9 119.50(12) . . ?
C4 C3 C2 121.29(12) . . ?
C9 C3 C2 119.22(13) . . ?
C12 C4 C3 119.90(13) . . ?
C12 C4 C5 119.85(13) . . ?
C3 C4 C5 120.24(12) . . ?
O2 C5 N1 119.18(13) . . ?
O2 C5 C4 124.97(12) . . ?
N1 C5 C4 115.85(12) . . ?
C7 C8 C9 121.22(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C7 C6 120.44(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C2 C6 C7 120.48(14) . . ?
C2 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C10 C9 C8 123.27(14) . . ?
C10 C9 C3 118.41(14) . . ?
C8 C9 C3 118.32(13) . . ?
C11 C10 C9 121.10(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.47(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C4 C12 C11 120.61(15) . . ?
C4 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O3 C13 C14 125.60(13) . . ?
O3 C13 N1 118.25(13) . . ?
C14 C13 N1 116.14(11) . . ?
C19 C14 C15 119.21(14) . . ?
C19 C14 C13 117.84(12) . . ?
C15 C14 C13 122.95(13) . . ?
C16 C15 C14 120.13(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.19(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.96(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.25(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.26(14) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
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 C1 1.2126(14) . ?
N1 C5 1.3951(16) . ?
N1 C1 1.4041(16) . ?
N1 C13 1.4726(16) . ?
C1 C2 1.4660(17) . ?
C2 C6 1.3666(18) . ?
C2 C3 1.4178(17) . ?
O2 C5 1.2155(15) . ?
O3 C13 1.1958(15) . ?
C3 C4 1.4114(18) . ?
C3 C9 1.4164(17) . ?
C4 C12 1.3732(18) . ?
C4 C5 1.4652(18) . ?
C8 C7 1.359(2) . ?
C8 C9 1.413(2) . ?
C8 H8 0.9300 . ?
C7 C6 1.3969(18) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.412(2) . ?
C10 C11 1.356(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.4665(18) . ?
C14 C19 1.3852(17) . ?
C14 C15 1.3872(18) . ?
C15 C16 1.374(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(2) . ?
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
C5 N1 C1 O1 176.63(12) . . . . ?
C13 N1 C1 O1 3.05(17) . . . . ?
C5 N1 C1 C2 -3.14(18) . . . . ?
C13 N1 C1 C2 -176.72(11) . . . . ?
O1 C1 C2 C6 3.0(2) . . . . ?
N1 C1 C2 C6 -177.28(12) . . . . ?
O1 C1 C2 C3 -176.05(12) . . . . ?
N1 C1 C2 C3 3.71(16) . . . . ?
C6 C2 C3 C4 178.61(12) . . . . ?
C1 C2 C3 C4 -2.38(17) . . . . ?
C6 C2 C3 C9 -1.49(17) . . . . ?
C1 C2 C3 C9 177.51(11) . . . . ?
C9 C3 C4 C12 -0.36(18) . . . . ?
C2 C3 C4 C12 179.54(11) . . . . ?
C9 C3 C4 C5 -179.77(11) . . . . ?
C2 C3 C4 C5 0.13(18) . . . . ?
C1 N1 C5 O2 -179.15(12) . . . . ?
C13 N1 C5 O2 -5.64(17) . . . . ?
C1 N1 C5 C4 1.00(18) . . . . ?
C13 N1 C5 C4 174.52(11) . . . . ?
C12 C4 C5 O2 1.4(2) . . . . ?
C3 C4 C5 O2 -179.21(12) . . . . ?
C12 C4 C5 N1 -178.78(11) . . . . ?
C3 C4 C5 N1 0.63(17) . . . . ?
C9 C8 C7 C6 -1.4(2) . . . . ?
C3 C2 C6 C7 1.05(19) . . . . ?
C1 C2 C6 C7 -177.96(12) . . . . ?
C8 C7 C6 C2 0.4(2) . . . . ?
C7 C8 C9 C10 -179.30(13) . . . . ?
C7 C8 C9 C3 0.9(2) . . . . ?
C4 C3 C9 C10 0.63(17) . . . . ?
C2 C3 C9 C10 -179.27(11) . . . . ?
C4 C3 C9 C8 -179.59(12) . . . . ?
C2 C3 C9 C8 0.51(17) . . . . ?
C8 C9 C10 C11 179.98(14) . . . . ?
C3 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C3 C4 C12 C11 -0.3(2) . . . . ?
C5 C4 C12 C11 179.11(13) . . . . ?
C10 C11 C12 C4 0.7(2) . . . . ?
C5 N1 C13 O3 -83.62(15) . . . . ?
C1 N1 C13 O3 90.62(15) . . . . ?
C5 N1 C13 C14 97.47(13) . . . . ?
C1 N1 C13 C14 -88.29(14) . . . . ?
O3 C13 C14 C19 3.1(2) . . . . ?
N1 C13 C14 C19 -178.09(12) . . . . ?
O3 C13 C14 C15 -177.08(14) . . . . ?
N1 C13 C14 C15 1.74(18) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 179.35(12) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C14 0.2(2) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
C13 C14 C19 C18 -179.52(12) . . . . ?
