#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024138.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_4024138
loop_
_publ_author_name
'Claudia L. Molina'
'Chun P. Chow'
'Kenneth J. Shea'
_publ_section_title
;
 Intramolecular N-Acylazo Diels-Alder Reaction: Regio- and
 Stereoselective Synthesis of Bridgehead Bicyclic 1,2-Diazines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6816
_journal_page_last               6823
_journal_paper_doi               10.1021/jo070978f
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.930(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9659(8)
_cell_length_b                   13.1890(12)
_cell_length_c                   10.8474(10)
_cell_measurement_temperature    163(2)
_cell_volume                     1259.4(2)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12777
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0356
_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)+(0.0447P)²+0.4509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                2427
_reflns_number_total             2775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070978f-File002.cif
_cod_data_source_block           kjs15
_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:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024138
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96628(10) 0.23100(6) 0.96524(7) 0.0277(2) Uani 1 1 d . . .
N1 N 0.70627(11) 0.15066(7) 0.84636(9) 0.0238(2) Uani 1 1 d . . .
N2 N 0.81527(10) 0.18812(7) 0.77858(8) 0.0200(2) Uani 1 1 d . . .
C1 C 0.95514(12) 0.21443(8) 0.85323(10) 0.0203(2) Uani 1 1 d . . .
C2 C 1.08953(13) 0.22541(8) 0.78746(11) 0.0218(2) Uani 1 1 d . . .
C3 C 1.18984(13) 0.12914(9) 0.78979(11) 0.0245(2) Uani 1 1 d . . .
C4 C 1.14722(14) 0.05430(9) 0.68044(11) 0.0263(3) Uani 1 1 d . . .
C5 C 1.02574(14) -0.02586(9) 0.69372(11) 0.0265(3) Uani 1 1 d . . .
C6 C 0.89493(13) 0.02049(8) 0.74179(10) 0.0218(2) Uani 1 1 d . . .
C7 C 0.85770(13) -0.00482(8) 0.85099(11) 0.0238(2) Uani 1 1 d . . .
C8 C 0.74848(14) 0.05481(9) 0.91241(11) 0.0251(2) Uani 1 1 d . . .
C9 C 0.82407(13) 0.11550(8) 0.67711(10) 0.0212(2) Uani 1 1 d . . .
C10 C 0.61831(12) 0.22291(9) 0.89390(10) 0.0238(2) Uani 1 1 d . . .
C11 C 0.54315(13) 0.19897(11) 0.99218(11) 0.0291(3) Uani 1 1 d . . .
C12 C 0.44453(14) 0.26925(12) 1.03044(12) 0.0344(3) Uani 1 1 d . . .
C13 C 0.41992(14) 0.36296(11) 0.97345(12) 0.0338(3) Uani 1 1 d . . .
C14 C 0.49665(14) 0.38770(10) 0.87744(12) 0.0311(3) Uani 1 1 d . . .
C15 C 0.59532(13) 0.31920(9) 0.83841(11) 0.0263(3) Uani 1 1 d . . .
H2A H 1.0587(15) 0.2485(10) 0.7012(13) 0.024(3) Uiso 1 1 d . . .
H2B H 1.1510(17) 0.2765(11) 0.8323(13) 0.029(4) Uiso 1 1 d . . .
H3A H 1.2921(17) 0.1542(11) 0.7882(13) 0.029(3) Uiso 1 1 d . . .
H3B H 1.1954(15) 0.0938(11) 0.8720(13) 0.027(3) Uiso 1 1 d . . .
H4A H 1.1165(16) 0.0947(11) 0.6022(13) 0.029(3) Uiso 1 1 d . . .
H4B H 1.2401(17) 0.0173(11) 0.6700(13) 0.032(4) Uiso 1 1 d . . .
H5A H 1.0708(16) -0.0792(11) 0.7538(13) 0.029(3) Uiso 1 1 d . . .
H5B H 0.9931(16) -0.0581(11) 0.6109(14) 0.032(4) Uiso 1 1 d . . .
H7A H 0.9060(16) -0.0609(11) 0.8998(13) 0.030(4) Uiso 1 1 d . . .
H8A H 0.7947(16) 0.0661(11) 1.0041(13) 0.030(4) Uiso 1 1 d . . .
H8B H 0.6519(17) 0.0164(11) 0.9100(13) 0.032(4) Uiso 1 1 d . . .
H9A H 0.8853(15) 0.1450(10) 0.6192(12) 0.021(3) Uiso 1 1 d . . .
H9B H 0.7189(16) 0.1052(10) 0.6304(13) 0.027(3) Uiso 1 1 d . . .
H11 H 0.5572(16) 0.1331(12) 1.0307(14) 0.033(4) Uiso 1 1 d . . .
H12 H 0.3932(18) 0.2510(12) 1.0976(15) 0.041(4) Uiso 1 1 d . . .
H13 H 0.3502(19) 0.4119(12) 1.0020(15) 0.040(4) Uiso 1 1 d . . .
H14 H 0.4788(18) 0.4570(13) 0.8376(15) 0.040(4) Uiso 1 1 d . . .
H15 H 0.6480(16) 0.3338(11) 0.7717(14) 0.030(4) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 N2 116.52(9) . . ?
C10 N1 C8 121.27(9) . . ?
N2 N1 C8 114.46(9) . . ?
C1 N2 N1 114.57(8) . . ?
C1 N2 C9 115.09(8) . . ?
N1 N2 C9 107.50(8) . . ?
O1 C1 N2 121.01(10) . . ?
O1 C1 C2 121.89(10) . . ?
N2 C1 C2 117.05(9) . . ?
C1 C2 C3 115.02(9) . . ?
C4 C3 C2 117.03(10) . . ?
C3 C4 C5 116.42(10) . . ?
C6 C5 C4 111.41(9) . . ?
C7 C6 C5 123.41(11) . . ?
C7 C6 C9 117.71(10) . . ?
C5 C6 C9 117.55(10) . . ?
C6 C7 C8 123.76(10) . . ?
N1 C8 C7 111.29(9) . . ?
N2 C9 C6 105.60(8) . . ?
N1 C10 C11 120.93(11) . . ?
N1 C10 C15 120.41(10) . . ?
C11 C10 C15 118.52(11) . . ?
C12 C11 C10 119.95(13) . . ?
C13 C12 C11 121.14(12) . . ?
C12 C13 C14 119.03(12) . . ?
C15 C14 C13 120.71(13) . . ?
C14 C15 C10 120.61(12) . . ?
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 1.2198(13) . ?
N1 C10 1.3965(14) . ?
N1 N2 1.4185(12) . ?
N1 C8 1.4669(15) . ?
N2 C1 1.4013(14) . ?
N2 C9 1.4725(14) . ?
C1 C2 1.5191(15) . ?
C2 C3 1.5534(16) . ?
C3 C4 1.5348(17) . ?
C4 C5 1.5441(17) . ?
C5 C6 1.5010(16) . ?
C6 C7 1.3327(16) . ?
C6 C9 1.5156(15) . ?
C7 C8 1.5062(16) . ?
C10 C11 1.4010(16) . ?
C10 C15 1.4038(17) . ?
C11 C12 1.3973(18) . ?
C12 C13 1.381(2) . ?
C13 C14 1.3913(19) . ?
C14 C15 1.3857(17) . ?
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
C10 N1 N2 C1 85.64(11) . . . . ?
C8 N1 N2 C1 -64.17(12) . . . . ?
C10 N1 N2 C9 -145.08(9) . . . . ?
C8 N1 N2 C9 65.11(11) . . . . ?
N1 N2 C1 O1 -19.72(14) . . . . ?
C9 N2 C1 O1 -145.12(10) . . . . ?
N1 N2 C1 C2 162.68(9) . . . . ?
C9 N2 C1 C2 37.28(13) . . . . ?
O1 C1 C2 C3 87.69(13) . . . . ?
N2 C1 C2 C3 -94.74(12) . . . . ?
C1 C2 C3 C4 90.43(12) . . . . ?
C2 C3 C4 C5 -85.86(13) . . . . ?
C3 C4 C5 C6 44.34(14) . . . . ?
C4 C5 C6 C7 -117.05(12) . . . . ?
C4 C5 C6 C9 49.43(13) . . . . ?
C5 C6 C7 C8 167.17(10) . . . . ?
C9 C6 C7 C8 0.71(16) . . . . ?
C10 N1 C8 C7 -173.46(10) . . . . ?
N2 N1 C8 C7 -25.22(13) . . . . ?
C6 C7 C8 N1 -8.07(16) . . . . ?
C1 N2 C9 C6 60.66(11) . . . . ?
N1 N2 C9 C6 -68.32(10) . . . . ?
C7 C6 C9 N2 36.61(13) . . . . ?
C5 C6 C9 N2 -130.66(10) . . . . ?
N2 N1 C10 C11 -160.04(10) . . . . ?
C8 N1 C10 C11 -12.43(16) . . . . ?
N2 N1 C10 C15 24.20(15) . . . . ?
C8 N1 C10 C15 171.81(10) . . . . ?
N1 C10 C11 C12 -174.03(11) . . . . ?
C15 C10 C11 C12 1.80(17) . . . . ?
C10 C11 C12 C13 -0.38(18) . . . . ?
C11 C12 C13 C14 -0.85(19) . . . . ?
C12 C13 C14 C15 0.62(19) . . . . ?
C13 C14 C15 C10 0.85(18) . . . . ?
N1 C10 C15 C14 173.82(11) . . . . ?
C11 C10 C15 C14 -2.04(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658841
