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#$Date: 2019-11-11 20:25:40 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227260 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035846.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_4035846
loop_
_publ_author_name
'Skalenko, Yevhen A.'
'Druzhenko, Tetiana V.'
'Denisenko, Aleksandr V.'
'Samoilenko, Maryna V.'
'Dacenko, Oleksandr P.'
'Trofymchuk, Serhii A.'
'Grygorenko, Oleksandr O.'
'Tolmachev, Andrey A.'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 [2+2]-Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach
 to Functional 3-Azabicyclo[3.2.0]heptanes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6275
_journal_page_last               6289
_journal_paper_doi               10.1021/acs.joc.8b00077
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C11 H13 N'
_chemical_formula_weight         159.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.874(2)
_cell_length_b                   8.3249(15)
_cell_length_c                   19.940(4)
_cell_measurement_reflns_used    464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.8
_cell_measurement_theta_min      3.7
_cell_volume                     1805.1(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11268
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         3.247
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0468
_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)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                774
_reflns_number_total             1540
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00077_si_002.cif
_cod_data_source_block           41
_cod_database_code               4035846
_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.
;
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
N1 N 0.44601(16) 0.26173(19) 0.54884(9) 0.0518(5) Uani 1 1 d . .
C1 C 0.53673(19) 0.0189(2) 0.44950(10) 0.0481(6) Uani 1 1 d . .
H1 H 0.5712 0.1190 0.4318 0.058 Uiso 1 1 calc R U
C2 C 0.40880(19) 0.0356(2) 0.48176(10) 0.0500(6) Uani 1 1 d . .
H2 H 0.3458 -0.0360 0.4633 0.060 Uiso 1 1 calc R U
C3 C 0.3667(2) 0.2055(2) 0.49395(11) 0.0578(7) Uani 1 1 d . .
H3A H 0.3777 0.2709 0.4541 0.069 Uiso 1 1 calc R U
H3B H 0.2808 0.2082 0.5070 0.069 Uiso 1 1 calc R U
C4 C 0.4465(2) 0.1262(2) 0.59536(11) 0.0575(6) Uani 1 1 d . .
H4A H 0.3695 0.1199 0.6198 0.069 Uiso 1 1 calc R U
H4B H 0.5136 0.1353 0.6272 0.069 Uiso 1 1 calc R U
C5 C 0.4016(2) 0.4114(2) 0.57774(12) 0.0652(7) Uani 1 1 d . .
H5A H 0.3236 0.3908 0.5998 0.078 Uiso 1 1 calc R U
H5B H 0.3864 0.4870 0.5417 0.078 Uiso 1 1 calc R U
C6 C 0.4876(2) 0.4880(2) 0.62749(11) 0.0521(6) Uani 1 1 d . .
C7 C 0.4424(2) 0.6051(3) 0.66958(12) 0.0682(7) Uani 1 1 d . .
H7 H 0.3587 0.6282 0.6687 0.082 Uiso 1 1 calc R U
C8 C 0.5172(3) 0.6890(3) 0.71284(13) 0.0824(9) Uani 1 1 d . .
H8 H 0.4847 0.7696 0.7399 0.099 Uiso 1 1 calc R U
C9 C 0.6398(3) 0.6531(3) 0.71583(13) 0.0793(9) Uani 1 1 d . .
H9 H 0.6910 0.7090 0.7450 0.095 Uiso 1 1 calc R U
C10 C 0.6873(2) 0.5337(3) 0.67545(13) 0.0697(8) Uani 1 1 d . .
H10 H 0.7704 0.5080 0.6779 0.084 Uiso 1 1 calc R U
C11 C 0.6115(2) 0.4523(2) 0.63137(11) 0.0596(7) Uani 1 1 d . .
H11 H 0.6442 0.3726 0.6040 0.072 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'
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
C5 N1 C4 114.26(17) . .
C5 N1 C3 111.88(17) . .
C4 N1 C3 103.23(16) . .
C4 C1 C2 115.37(16) 5_656 .
C4 C1 C2 103.97(15) 5_656 5_656
C2 C1 C2 90.13(17) . 5_656
C3 C2 C1 115.29(16) . .
C3 C2 C1 104.27(17) . 5_656
C1 C2 C1 89.87(17) . 5_656
N1 C3 C2 103.94(17) . .
N1 C4 C1 103.97(16) . 5_656
N1 C5 C6 114.68(19) . .
C7 C6 C11 117.8(2) . .
C7 C6 C5 118.7(2) . .
C11 C6 C5 123.5(2) . .
C8 C7 C6 122.0(3) . .
C9 C8 C7 119.5(3) . .
C8 C9 C10 119.8(3) . .
C9 C10 C11 120.1(3) . .
C6 C11 C10 120.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.455(2) .
N1 C4 1.461(2) .
N1 C3 1.470(2) .
C1 C4 1.514(2) 5_656
C1 C2 1.539(3) .
C1 C2 1.560(3) 5_656
C2 C3 1.506(2) .
C2 C1 1.560(3) 5_656
C4 C1 1.514(2) 5_656
C5 C6 1.505(3) .
C6 C7 1.377(3) .
C6 C11 1.382(3) .
C7 C8 1.376(3) .
C8 C9 1.367(4) .
C9 C10 1.379(3) .
C10 C11 1.383(3) .
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_4
C4 C1 C2 C3 -148.68(17) 5_656 .
C2 C1 C2 C3 105.8(2) 5_656 .
C4 C1 C2 C1 105.56(19) 5_656 5_656
C2 C1 C2 C1 0.001(0) 5_656 5_656
C5 N1 C3 C2 -167.37(17) . .
C4 N1 C3 C2 -44.0(2) . .
C1 C2 C3 N1 -70.5(2) . .
C1 C2 C3 N1 26.3(2) 5_656 .
C5 N1 C4 C1 165.82(17) . 5_656
C3 N1 C4 C1 44.09(19) . 5_656
C4 N1 C5 C6 71.4(2) . .
C3 N1 C5 C6 -171.78(18) . .
N1 C5 C6 C7 -163.82(19) . .
N1 C5 C6 C11 19.1(3) . .
C11 C6 C7 C8 2.1(3) . .
C5 C6 C7 C8 -175.1(2) . .
C6 C7 C8 C9 -1.8(4) . .
C7 C8 C9 C10 0.2(4) . .
C8 C9 C10 C11 1.0(4) . .
C7 C6 C11 C10 -1.0(3) . .
C5 C6 C11 C10 176.1(2) . .
C9 C10 C11 C6 -0.5(3) . .
