#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/77/2217769.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_2217769
loop_
_publ_author_name
'Sha, Fei'
'Xu, Hao'
'Liu, Shan'
'Wang, Peng'
'Wang, Jin-tang'
_publ_section_title
;
 1-Benzyl-1,4-diazepan-5-one
;
_journal_coeditor_code           FL2179
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o569
_journal_paper_doi               10.1107/S1600536808001773
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H16 N2 O'
_chemical_formula_moiety         'C12 H16 N2 O'
_chemical_formula_sum            'C12 H16 N2 O'
_chemical_formula_weight         204.27
_chemical_name_systematic
;
1-Benzyl-1,4-diazepan-5-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.00(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.602(3)
_cell_length_b                   7.4920(15)
_cell_length_c                   12.824(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1130.3(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2308
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.0877
_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)+(0.04P)²+1.65P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                1162
_reflns_number_total             2205
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2179.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1130.3(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217769
_cod_database_fobs_code          2217769
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
N N1 0.3935(3) -0.4319(6) 0.5667(3) 0.0870(12) Uani d U 1
H H1A 0.4312 -0.5275 0.5667 0.104 Uiso calc R 1
O O 0.5027(3) -0.2681(5) 0.4894(3) 0.108 Uani d D 1
N N2 0.2757(3) -0.1384(4) 0.6724(2) 0.0542(8) Uani d . 1
C C1 0.2993(4) -0.4434(5) 0.6094(4) 0.0705(12) Uani d U 1
H H1B 0.2940 -0.5657 0.6319 0.085 Uiso calc R 1
H H1C 0.2289 -0.4158 0.5487 0.085 Uiso calc R 1
C C2 0.3090(4) -0.3232(5) 0.7059(4) 0.0697(11) Uani d U 1
H H2A 0.2613 -0.3696 0.7446 0.084 Uiso calc R 1
H H2B 0.3869 -0.3245 0.7579 0.084 Uiso calc R 1
C C3 0.3581(3) -0.0442(5) 0.6349(3) 0.0632(10) Uani d U 1
H H3A 0.4334 -0.0571 0.6912 0.076 Uiso calc R 1
H H3B 0.3396 0.0820 0.6278 0.076 Uiso calc R 1
C C4 0.3596(3) -0.1132(6) 0.5236(3) 0.0683(11) Uani d U 1
H H4A 0.2817 -0.1299 0.4735 0.082 Uiso calc R 1
H H4B 0.3932 -0.0222 0.4913 0.082 Uiso calc R 1
C C5 0.4230(3) -0.2848(7) 0.5289(4) 0.0765(13) Uani d DU 1
C C6 0.2595(3) -0.0404(6) 0.7642(3) 0.0685(12) Uani d . 1
H H6A 0.3332 -0.0018 0.8157 0.082 Uiso calc R 1
H H6B 0.2272 -0.1204 0.8043 0.082 Uiso calc R 1
C C7 0.1827(3) 0.1221(5) 0.7265(3) 0.0531(9) Uani d . 1
C C8 0.1029(3) 0.1333(5) 0.6142(4) 0.0643(11) Uani d . 1
H H8A 0.1017 0.0489 0.5606 0.077 Uiso calc R 1
C C9 0.0285(4) 0.2739(6) 0.5892(4) 0.0779(13) Uani d . 1
H H9A -0.0223 0.2845 0.5161 0.094 Uiso calc R 1
C C10 0.0241(4) 0.3960(7) 0.6626(5) 0.0865(15) Uani d . 1
H H10A -0.0288 0.4879 0.6406 0.104 Uiso calc R 1
C C11 0.0969(5) 0.3858(6) 0.7691(5) 0.0869(15) Uani d . 1
H H11A 0.0954 0.4710 0.8213 0.104 Uiso calc R 1
C C12 0.1748(4) 0.2447(6) 0.7999(4) 0.0713(12) Uani d . 1
H H12A 0.2230 0.2354 0.8741 0.086 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.065(2) 0.109(3) 0.076(3) 0.031(2) 0.0121(19) -0.027(2)
O 0.108 0.108 0.108 0.000 0.039 0.000
N2 0.0666(19) 0.0520(18) 0.0461(17) 0.0091(16) 0.0229(15) -0.0087(15)
C1 0.084(3) 0.048(2) 0.083(3) 0.011(2) 0.034(2) -0.003(2)
C2 0.085(3) 0.050(2) 0.073(3) -0.004(2) 0.027(2) 0.011(2)
C3 0.072(3) 0.055(2) 0.070(3) -0.005(2) 0.035(2) 0.002(2)
C4 0.054(2) 0.089(3) 0.065(2) 0.012(2) 0.0255(19) 0.016(2)
C5 0.051(2) 0.100(3) 0.084(3) 0.017(2) 0.030(2) -0.033(3)
C6 0.069(3) 0.079(3) 0.055(2) 0.025(2) 0.020(2) 0.003(2)
C7 0.060(2) 0.048(2) 0.058(2) 0.0113(18) 0.0293(19) 0.0002(18)
C8 0.052(2) 0.058(2) 0.080(3) 0.003(2) 0.020(2) -0.009(2)
C9 0.064(3) 0.064(3) 0.092(3) 0.012(2) 0.011(2) 0.007(3)
C10 0.066(3) 0.074(3) 0.131(5) 0.018(3) 0.050(3) -0.009(3)
C11 0.098(4) 0.061(3) 0.119(4) 0.001(3) 0.061(4) -0.018(3)
C12 0.078(3) 0.064(3) 0.084(3) -0.011(2) 0.043(3) -0.003(2)
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'
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
C5 N1 C1 124.0(4)
C5 N1 H1A 118.0
C1 N1 H1A 118.0
C6 N2 C2 110.3(3)
C6 N2 C3 109.9(3)
C2 N2 C3 112.8(3)
N1 C1 C2 115.6(4)
N1 C1 H1B 108.4
C2 C1 H1B 108.4
N1 C1 H1C 108.4
C2 C1 H1C 108.4
H1B C1 H1C 107.4
N2 C2 C1 113.3(3)
N2 C2 H2A 108.9
C1 C2 H2A 108.9
N2 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.7
N2 C3 C4 113.0(3)
N2 C3 H3A 109.0
C4 C3 H3A 109.0
N2 C3 H3B 109.0
C4 C3 H3B 109.0
H3A C3 H3B 107.8
C5 C4 C3 115.7(3)
C5 C4 H4A 108.4
C3 C4 H4A 108.4
C5 C4 H4B 108.4
C3 C4 H4B 108.4
H4A C4 H4B 107.4
O C5 N1 126.5(4)
O C5 C4 112.2(5)
N1 C5 C4 121.3(3)
N2 C6 C7 113.7(3)
N2 C6 H6A 108.8
C7 C6 H6A 108.8
N2 C6 H6B 108.8
C7 C6 H6B 108.8
H6A C6 H6B 107.7
C12 C7 C8 117.6(4)
C12 C7 C6 121.5(4)
C8 C7 C6 120.2(3)
C9 C8 C7 117.1(4)
C9 C8 H8A 121.5
C7 C8 H8A 121.5
C10 C9 C8 124.2(5)
C10 C9 H9A 117.9
C8 C9 H9A 117.9
C9 C10 C11 119.6(5)
C9 C10 H10A 120.2
C11 C10 H10A 120.2
C10 C11 C12 118.9(5)
C10 C11 H11A 120.6
C12 C11 H11A 120.6
C7 C12 C11 122.6(4)
C7 C12 H12A 118.7
C11 C12 H12A 118.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.311(6)
N1 C1 1.477(5)
N1 H1A 0.8600
O C5 1.284(5)
N2 C6 1.462(4)
N2 C2 1.465(5)
N2 C3 1.471(4)
C1 C2 1.500(5)
C1 H1B 0.9700
C1 H1C 0.9700
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.525(5)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.502(6)
C4 H4A 0.9700
C4 H4B 0.9700
C6 C7 1.523(5)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C12 1.345(5)
C7 C8 1.433(5)
C8 C9 1.370(5)
C8 H8A 0.9300
C9 C10 1.328(6)
C9 H9A 0.9300
C10 C11 1.347(7)
C10 H10A 0.9300
C11 C12 1.400(6)
C11 H11A 0.9300
C12 H12A 0.9300
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
_geom_hbond_publ_flag
N1 H1A O 3_646 0.86 2.00 2.821(5) 160.3 yes
C4 H4B O 3_656 0.97 2.51 3.377(5) 149.4 yes
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
C5 N1 C1 C2 -58.5(6)
C6 N2 C2 C1 165.8(3)
C3 N2 C2 C1 -70.9(4)
N1 C1 C2 N2 79.5(5)
C6 N2 C3 C4 -166.9(3)
C2 N2 C3 C4 69.6(4)
N2 C3 C4 C5 -78.3(4)
C1 N1 C5 O -178.8(4)
C1 N1 C5 C4 -1.4(7)
C3 C4 C5 O -122.4(4)
C3 C4 C5 N1 59.8(6)
C2 N2 C6 C7 -157.2(3)
C3 N2 C6 C7 77.8(4)
N2 C6 C7 C12 -167.9(4)
N2 C6 C7 C8 22.3(5)
C12 C7 C8 C9 3.2(6)
C6 C7 C8 C9 173.4(4)
C7 C8 C9 C10 -1.8(7)
C8 C9 C10 C11 0.5(8)
C9 C10 C11 C12 -0.7(7)
C8 C7 C12 C11 -3.6(6)
C6 C7 C12 C11 -173.7(4)
C10 C11 C12 C7 2.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 209430
