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#$Date: 2017-11-06 01:06:28 +0200 (Mon, 06 Nov 2017) $
#$Revision: 202608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033052.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_4033052
loop_
_publ_author_name
'Denisenko, Aleksandr V.'
'Druzhenko, Tetiana'
'Skalenko, Yevhen'
'Samoilenko, Maryna'
'Grygorenko, Oleksandr O.'
'Zozulya, Sergey'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Photochemical Synthesis of 3-Azabicyclo[3.2.0]heptanes: Advanced Building
 Blocks for Drug Discovery.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9627
_journal_page_last               9636
_journal_paper_doi               10.1021/acs.joc.7b01678
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C12 H16 Cl N'
_chemical_formula_weight         209.71
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.45(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.846(2)
_cell_length_b                   7.3513(9)
_cell_length_c                   13.544(2)
_cell_measurement_reflns_used    1123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      3.3
_cell_volume                     1145.1(3)
_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 0.950
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12510
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.021
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0743
_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)+(0.1190P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1297
_reflns_number_total             3214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01678_si_002.cif
_cod_data_source_block           tolm307_20
_cod_original_cell_volume        1145.2(4)
_cod_database_code               4033052
_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   0.943
_shelx_estimated_absorpt_t_max   0.985
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
Cl1 Cl -0.09135(7) 0.74528(9) 0.10806(7) 0.0707(3) Uani 1 1 d . .
N1 N 0.0836(3) 0.6586(4) 0.3471(3) 0.0734(8) Uani 1 1 d . .
H1NA H 0.021(3) 0.668(6) 0.271(4) 0.098(12) Uiso 1 1 d . .
H1NB H 0.089(3) 0.534(7) 0.366(3) 0.121(15) Uiso 1 1 d . .
C1 C 0.1913(3) 0.7436(4) 0.3552(3) 0.0710(9) Uani 1 1 d . .
H1C H 0.1737 0.8512 0.3092 0.085 Uiso 1 1 calc R U
H1D H 0.2347 0.6589 0.3328 0.085 Uiso 1 1 calc R U
C2 C 0.2579(3) 0.7919(5) 0.4734(3) 0.0702(8) Uani 1 1 d . .
H2 H 0.3048 0.9022 0.4852 0.084 Uiso 1 1 calc R U
C3 C 0.3221(3) 0.6396(4) 0.5560(2) 0.0685(8) Uani 1 1 d . .
H3 H 0.3080 0.5227 0.5174 0.082 Uiso 1 1 calc R U
C4 C 0.2370(3) 0.6636(7) 0.6063(3) 0.0938(12) Uani 1 1 d . .
H4A H 0.1919 0.5552 0.6016 0.113 Uiso 1 1 calc R U
H4B H 0.2731 0.7105 0.6810 0.113 Uiso 1 1 calc R U
C5 C 0.1702(3) 0.8055(5) 0.5208(3) 0.0729(9) Uani 1 1 d . .
H5 H 0.1698 0.9250 0.5527 0.087 Uiso 1 1 calc R U
C6 C 0.0545(3) 0.7542(4) 0.4289(3) 0.0699(9) Uani 1 1 d . .
H6A H 0.0123 0.6744 0.4554 0.084 Uiso 1 1 calc R U
H6B H 0.0078 0.8615 0.3964 0.084 Uiso 1 1 calc R U
C7 C 0.4500(3) 0.6634(4) 0.6280(3) 0.0719(9) Uani 1 1 d . .
C8 C 0.5208(4) 0.7154(5) 0.5793(4) 0.0880(11) Uani 1 1 d . .
H8 H 0.4881 0.7355 0.5036 0.106 Uiso 1 1 calc R U
C9 C 0.6384(4) 0.7373(5) 0.6421(5) 0.1023(15) Uani 1 1 d . .
H9 H 0.6851 0.7674 0.6082 0.123 Uiso 1 1 calc R U
C10 C 0.6876(4) 0.7152(6) 0.7537(6) 0.1068(17) Uani 1 1 d . .
H10 H 0.7669 0.7329 0.7961 0.128 Uiso 1 1 calc R U
C11 C 0.6184(4) 0.6667(6) 0.8025(4) 0.1045(14) Uani 1 1 d . .
H11 H 0.6514 0.6517 0.8786 0.125 Uiso 1 1 calc R U
C12 C 0.5008(3) 0.6397(5) 0.7409(3) 0.0859(11) Uani 1 1 d . .
H12 H 0.4554 0.6055 0.7754 0.103 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C6 106.3(3)
C1 N1 H1NA 110(2)
C6 N1 H1NA 113(2)
C1 N1 H1NB 116(2)
C6 N1 H1NB 105(2)
H1NA N1 H1NB 106(4)
N1 C1 C2 104.6(3)
N1 C1 H1C 110.8
C2 C1 H1C 110.8
N1 C1 H1D 110.8
C2 C1 H1D 110.8
H1C C1 H1D 108.9
C1 C2 C5 106.8(3)
C1 C2 C3 118.4(3)
C5 C2 C3 89.9(2)
C1 C2 H2 113.1
C5 C2 H2 113.1
C3 C2 H2 113.1
C7 C3 C4 119.3(3)
C7 C3 C2 117.7(3)
C4 C3 C2 89.0(2)
C7 C3 H3 109.8
C4 C3 H3 109.8
C2 C3 H3 109.8
C5 C4 C3 90.7(3)
C5 C4 H4A 113.5
C3 C4 H4A 113.5
C5 C4 H4B 113.5
C3 C4 H4B 113.5
H4A C4 H4B 110.8
C6 C5 C4 118.5(3)
C6 C5 C2 106.2(3)
C4 C5 C2 90.2(3)
C6 C5 H5 113.2
C4 C5 H5 113.2
C2 C5 H5 113.2
N1 C6 C5 104.5(3)
N1 C6 H6A 110.8
C5 C6 H6A 110.8
N1 C6 H6B 110.8
C5 C6 H6B 110.8
H6A C6 H6B 108.9
C12 C7 C8 118.2(3)
C12 C7 C3 123.0(3)
C8 C7 C3 118.7(3)
C9 C8 C7 120.5(5)
C9 C8 H8 119.7
C7 C8 H8 119.7
C10 C9 C8 120.7(5)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 119.1(4)
C9 C10 H10 120.5
C11 C10 H10 120.5
C10 C11 C12 121.1(4)
C10 C11 H11 119.4
C12 C11 H11 119.4
C11 C12 C7 120.2(4)
C11 C12 H12 119.9
C7 C12 H12 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.477(4)
N1 C6 1.493(5)
N1 H1NA 0.99(4)
N1 H1NB 0.95(5)
C1 C2 1.483(5)
C1 H1C 0.9700
C1 H1D 0.9700
C2 C5 1.528(5)
C2 C3 1.538(4)
C2 H2 0.9800
C3 C7 1.501(5)
C3 C4 1.535(5)
C3 H3 0.9800
C4 C5 1.511(6)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.500(5)
C5 H5 0.9800
C6 H6A 0.9700
C6 H6B 0.9700
C7 C12 1.380(5)
C7 C8 1.393(5)
C8 C9 1.375(7)
C8 H8 0.9300
C9 C10 1.363(8)
C9 H9 0.9300
C10 C11 1.371(7)
C10 H10 0.9300
C11 C12 1.376(5)
C11 H11 0.9300
C12 H12 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1NA Cl1 0.99(4) 2.10(4) 3.075(3) 167(3) .
N1 H1NB Cl1 0.95(5) 2.15(5) 3.091(3) 174(4) 2_545
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
C6 N1 C1 C2 34.0(3)
N1 C1 C2 C5 -22.5(3)
N1 C1 C2 C3 76.9(3)
C1 C2 C3 C7 125.0(3)
C5 C2 C3 C7 -125.9(3)
C1 C2 C3 C4 -112.2(3)
C5 C2 C3 C4 -3.0(3)
C7 C3 C4 C5 124.6(3)
C2 C3 C4 C5 3.0(3)
C3 C4 C5 C6 105.5(3)
C3 C4 C5 C2 -3.0(3)
C1 C2 C5 C6 3.0(3)
C3 C2 C5 C6 -116.8(3)
C1 C2 C5 C4 122.8(3)
C3 C2 C5 C4 3.0(3)
C1 N1 C6 C5 -32.0(3)
C4 C5 C6 N1 -81.9(4)
C2 C5 C6 N1 17.4(3)
C4 C3 C7 C12 24.6(5)
C2 C3 C7 C12 130.3(3)
C4 C3 C7 C8 -154.0(3)
C2 C3 C7 C8 -48.3(4)
C12 C7 C8 C9 1.8(5)
C3 C7 C8 C9 -179.5(3)
C7 C8 C9 C10 -2.5(6)
C8 C9 C10 C11 1.5(6)
C9 C10 C11 C12 0.1(7)
C10 C11 C12 C7 -0.7(6)
C8 C7 C12 C11 -0.3(5)
C3 C7 C12 C11 -178.9(3)
