#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231201.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231201
loop_
_publ_author_name
'Fu, Ying'
'Ye, Fei'
_publ_section_title
;
 2,2-Dichloro-1-(3,3,6-trimethyl-9-oxo-1,5-diazabicyclo[4.3.0]nonan-5-yl)ethanone
;
_journal_coeditor_code           LH5271
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2020
_journal_paper_doi               10.1107/S1600536811027176
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H18 Cl2 N2 O2'
_chemical_formula_moiety         'C12 H18 Cl2 N2 O2'
_chemical_formula_sum            'C12 H18 Cl2 N2 O2'
_chemical_formula_weight         293.18
_chemical_name_systematic
;
2,2-Dichloro-1-(3,3,6-trimethyl-9-oxo-1,5-diazabicyclo[4.3.0]nonan-5-yl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 115.067(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4442(18)
_cell_length_b                   14.116(3)
_cell_length_c                   11.7555(16)
_cell_measurement_reflns_used    3515
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.38
_cell_volume                     1419.6(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10829
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.478
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.2384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                2556
_reflns_number_total             3492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5271.cif
_cod_data_source_block           I
_cod_original_cell_volume        1419.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231201
_cod_database_fobs_code          2231201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.38732(6) -0.01048(4) 0.34216(5) 0.05901(18) Uani d . 1 1
Cl Cl2 0.21200(7) -0.01735(4) 0.07141(6) 0.0696(2) Uani d . 1 1
O O1 0.43042(15) -0.18995(10) 0.24212(16) 0.0618(4) Uani d . 1 1
O O2 0.06902(18) -0.54370(10) 0.24058(16) 0.0638(4) Uani d . 1 1
N N1 0.17907(15) -0.24099(9) 0.17670(13) 0.0342(3) Uani d . 1 1
N N2 0.10521(16) -0.40443(10) 0.15860(14) 0.0388(3) Uani d . 1 1
C C1 0.2408(2) -0.07096(12) 0.21585(17) 0.0419(4) Uani d . 1 1
H H1 0.1428 -0.0703 0.2257 0.050 Uiso calc R 1 1
C C2 0.29300(19) -0.17366(12) 0.21273(17) 0.0399(4) Uani d . 1 1
C C3 0.01328(18) -0.21728(12) 0.09737(15) 0.0364(4) Uani d . 1 1
H H3A -0.0029 -0.2147 0.0102 0.044 Uiso calc R 1 1
H H3B -0.0089 -0.1549 0.1205 0.044 Uiso calc R 1 1
C C4 -0.10098(18) -0.28847(12) 0.10984(15) 0.0366(4) Uani d . 1 1
C C5 -0.2656(2) -0.26170(16) 0.0151(2) 0.0581(5) Uani d . 1 1
H H5A -0.2699 -0.2615 -0.0679 0.087 Uiso calc R 1 1
H H5B -0.2913 -0.1998 0.0346 0.087 Uiso calc R 1 1
H H5C -0.3392 -0.3070 0.0193 0.087 Uiso calc R 1 1
C C6 -0.0909(2) -0.28828(14) 0.24271(18) 0.0485(4) Uani d . 1 1
H H6A -0.1645 -0.3329 0.2480 0.073 Uiso calc R 1 1
H H6B -0.1148 -0.2261 0.2627 0.073 Uiso calc R 1 1
H H6C 0.0128 -0.3057 0.3011 0.073 Uiso calc R 1 1
C C7 -0.0579(2) -0.38544(12) 0.07744(17) 0.0419(4) Uani d . 1 1
H H7A -0.1235 -0.4337 0.0893 0.050 Uiso calc R 1 1
H H7B -0.0742 -0.3866 -0.0098 0.050 Uiso calc R 1 1
C C8 0.22976(19) -0.33990(11) 0.16558(16) 0.0367(4) Uani d . 1 1
C C9 0.2611(2) -0.34929(15) 0.04896(19) 0.0516(5) Uani d . 1 1
H H9A 0.2991 -0.4119 0.0457 0.077 Uiso calc R 1 1
H H9B 0.3380 -0.3035 0.0525 0.077 Uiso calc R 1 1
H H9C 0.1660 -0.3384 -0.0247 0.077 Uiso calc R 1 1
C C10 0.3679(2) -0.37342(13) 0.28688(18) 0.0477(4) Uani d . 1 1
H H10A 0.4655 -0.3695 0.2784 0.057 Uiso calc R 1 1
H H10B 0.3763 -0.3353 0.3582 0.057 Uiso calc R 1 1
C C11 0.3290(2) -0.47623(14) 0.3029(2) 0.0531(5) Uani d . 1 1
H H11A 0.3784 -0.5195 0.2666 0.064 Uiso calc R 1 1
H H11B 0.3628 -0.4917 0.3909 0.064 Uiso calc R 1 1
C C12 0.1545(2) -0.48091(12) 0.23385(19) 0.0454(4) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C3 121.54(13)
C2 N1 C8 115.95(13)
C3 N1 C8 116.53(12)
C12 N2 C7 123.66(15)
C12 N2 C8 114.61(15)
C7 N2 C8 121.72(14)
C2 C1 Cl1 109.38(12)
C2 C1 Cl2 107.50(13)
Cl1 C1 Cl2 110.34(9)
C2 C1 H1 109.9
Cl1 C1 H1 109.9
Cl2 C1 H1 109.9
O1 C2 N1 124.36(16)
O1 C2 C1 119.10(15)
N1 C2 C1 116.54(14)
N1 C3 C4 113.10(13)
N1 C3 H3A 109.0
C4 C3 H3A 109.0
N1 C3 H3B 109.0
C4 C3 H3B 109.0
H3A C3 H3B 107.8
C7 C4 C6 110.55(14)
C7 C4 C3 107.05(14)
C6 C4 C3 110.96(14)
C7 C4 C5 109.74(15)
C6 C4 C5 110.41(16)
C3 C4 C5 108.05(15)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 C4 108.86(13)
N2 C7 H7A 109.9
C4 C7 H7A 109.9
N2 C7 H7B 109.9
C4 C7 H7B 109.9
H7A C7 H7B 108.3
N2 C8 N1 107.82(13)
N2 C8 C9 110.68(14)
N1 C8 C9 110.48(14)
N2 C8 C10 101.88(14)
N1 C8 C10 112.40(13)
C9 C8 C10 113.16(15)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C8 104.57(15)
C11 C10 H10A 110.8
C8 C10 H10A 110.8
C11 C10 H10B 110.8
C8 C10 H10B 110.8
H10A C10 H10B 108.9
C12 C11 C10 104.01(15)
C12 C11 H11A 111.0
C10 C11 H11A 111.0
C12 C11 H11B 111.0
C10 C11 H11B 111.0
H11A C11 H11B 109.0
O2 C12 N2 124.68(19)
O2 C12 C11 126.95(18)
N2 C12 C11 108.34(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7627(18)
Cl2 C1 1.7715(19)
O1 C2 1.215(2)
O2 C12 1.224(2)
N1 C2 1.362(2)
N1 C3 1.482(2)
N1 C8 1.499(2)
N2 C12 1.348(2)
N2 C7 1.452(2)
N2 C8 1.462(2)
C1 C2 1.537(2)
C1 H1 0.9800
C3 C4 1.527(2)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C7 1.522(2)
C4 C6 1.524(2)
C4 C5 1.528(2)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.526(2)
C8 C10 1.544(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.528(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.499(3)
C11 H11A 0.9700
C11 H11B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 O2 2_555 0.98 2.23 3.200(3) 170
C3 H3B O2 2_555 0.97 2.50 3.390(2) 153
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 103079
