#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/70/1517021.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_1517021
loop_
_publ_author_name
'Schurgers, Ben'
'Brigou, Ben'
'Urbanczyk-Lipkowska, Zofia'
'Tourwé, Dirk'
'Ballet, Steven'
'De Proft, Frank'
'Van Lommen, Guy'
'Verniest, Guido'
_publ_section_title
;
 Synthesis of Fused 3-Aminoazepinones via Trapping of a New Class of
 Cyclic Seven-Membered Allenamides with Furan.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3712
_journal_page_last               3715
_journal_paper_doi               10.1021/ol501529z
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H26 N2 O4'
_chemical_formula_weight         382.45
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.924(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9180(4)
_cell_length_b                   26.3168(9)
_cell_length_c                   7.8796(3)
_cell_measurement_reflns_used    6638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.95
_cell_measurement_theta_min      3.36
_cell_volume                     2037.02(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            24263
_diffrn_reflns_theta_full        67.73
_diffrn_reflns_theta_max         67.73
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0702P)²+0.3735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3099
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501529z_si_002.cif
_cod_data_source_block           a_0ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517020--1517021.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1517021
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
O4 O 0.74739(11) 0.46777(4) 0.32914(15) 0.0590(3) Uani 1 1 d .
N2 N 0.67138(14) 0.52360(5) 0.50287(18) 0.0525(3) Uani 1 1 d .
O2 O 0.43875(12) 0.56611(4) 0.33831(14) 0.0611(3) Uani 1 1 d .
O3 O 0.78188(15) 0.55231(5) 0.29010(17) 0.0728(4) Uani 1 1 d .
C9 C 0.63638(15) 0.57381(5) 0.5535(2) 0.0474(3) Uani 1 1 d .
N1 N 0.50104(14) 0.64582(5) 0.41951(17) 0.0556(3) Uani 1 1 d .
C14 C 0.7917(4) 0.47284(10) 0.0316(3) 0.1122(10) Uani 1 1 d .
H14A H 0.6960 0.4671 -0.0006 0.168 Uiso 1 1 calc R
H14B H 0.8413 0.4569 -0.0502 0.168 Uiso 1 1 calc R
H14C H 0.8095 0.5087 0.0339 0.168 Uiso 1 1 calc R
C12 C 0.83555(16) 0.45088(6) 0.20512(19) 0.0543(4) Uani 1 1 d .
C11 C 0.73735(15) 0.51744(6) 0.3666(2) 0.0524(4) Uani 1 1 d .
C10 C 0.51538(15) 0.59450(6) 0.42885(18) 0.0485(3) Uani 1 1 d .
C16 C 0.39769(19) 0.66773(7) 0.2873(2) 0.0653(5) Uani 1 1 d .
H16A H 0.3817 0.6441 0.1920 0.078 Uiso 1 1 calc R
H16B H 0.4336 0.6988 0.2450 0.078 Uiso 1 1 calc R
C17 C 0.26420(18) 0.67930(6) 0.3484(2) 0.0602(4) Uani 1 1 d .
C18 C 0.1569(2) 0.64579(8) 0.3183(2) 0.0701(5) Uani 1 1 d .
H18 H 0.1688 0.6151 0.2640 0.084 Uiso 1 1 calc R
C19 C 0.0317(2) 0.65710(10) 0.3677(3) 0.0872(6) Uani 1 1 d .
H19 H -0.0405 0.6345 0.3444 0.105 Uiso 1 1 calc R
C20 C 0.0147(3) 0.70190(12) 0.4512(3) 0.0981(8) Uani 1 1 d .
H20 H -0.0694 0.7096 0.4844 0.118 Uiso 1 1 calc R
C13 C 0.9808(2) 0.46394(11) 0.2774(4) 0.0990(8) Uani 1 1 d .
H13A H 0.9927 0.5001 0.2763 0.148 Uiso 1 1 calc R
H13B H 1.0420 0.4483 0.2088 0.148 Uiso 1 1 calc R
H13C H 0.9999 0.4517 0.3930 0.148 Uiso 1 1 calc R
C8 C 0.60813(17) 0.57347(6) 0.7380(2) 0.0524(4) Uani 1 1 d .
C7 C 0.57871(17) 0.62653(6) 0.8039(2) 0.0543(4) Uani 1 1 d .
C2 C 0.61569(15) 0.67097(5) 0.6967(2) 0.0515(4) Uani 1 1 d .
C1 C 0.57751(17) 0.67991(6) 0.5334(2) 0.0563(4) Uani 1 1 d .
C22 C 0.2447(2) 0.72416(8) 0.4337(3) 0.0864(7) Uani 1 1 d .
H22 H 0.3160 0.7472 0.4563 0.104 Uiso 1 1 calc R
C21 C 0.1198(3) 0.73508(11) 0.4857(3) 0.1058(10) Uani 1 1 d .
H21 H 0.1080 0.7651 0.5441 0.127 Uiso 1 1 calc R
C3 C 0.7046(2) 0.70438(6) 0.8219(2) 0.0632(4) Uani 1 1 d .
C4 C 0.8366(2) 0.67573(7) 0.8671(3) 0.0696(5) Uani 1 1 d .
C5 C 0.8091(2) 0.63777(8) 0.9648(2) 0.0701(5) Uani 1 1 d .
C6 C 0.6608(2) 0.64237(7) 0.9797(2) 0.0696(5) Uani 1 1 d .
O1 O 0.64202(17) 0.69693(5) 0.97423(18) 0.0829(4) Uani 1 1 d .
C15 C 0.8170(2) 0.39387(7) 0.2012(3) 0.0690(5) Uani 1 1 d .
H15A H 0.8370 0.3806 0.3153 0.104 Uiso 1 1 calc R
H15B H 0.8775 0.3790 0.1300 0.104 Uiso 1 1 calc R
H15C H 0.7246 0.3858 0.1557 0.104 Uiso 1 1 calc R
H2N H 0.6395(18) 0.4984(7) 0.548(2) 0.052(4) Uiso 1 1 d .
H1 H 0.594(2) 0.7102(8) 0.482(2) 0.071(5) Uiso 1 1 d .
H3 H 0.7075(19) 0.7421(8) 0.791(2) 0.072(5) Uiso 1 1 d .
H5 H 0.863(2) 0.6090(9) 1.013(3) 0.094(7) Uiso 1 1 d .
H4 H 0.923(3) 0.6832(9) 0.815(3) 0.099(7) Uiso 1 1 d .
H6 H 0.630(2) 0.6275(8) 1.079(3) 0.079(6) Uiso 1 1 d .
H7 H 0.483(2) 0.6295(7) 0.814(3) 0.075(6) Uiso 1 1 d .
H8A H 0.690(2) 0.5581(7) 0.805(2) 0.066(5) Uiso 1 1 d .
H8B H 0.5288(19) 0.5508(7) 0.750(2) 0.060(5) Uiso 1 1 d .
H9 H 0.7127(16) 0.5963(6) 0.5470(19) 0.047(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C11 O4 C12 120.59(12)
C11 N2 C9 119.77(13)
C11 N2 H2N 120.0(12)
C9 N2 H2N 119.5(12)
N2 C9 C8 110.13(12)
N2 C9 C10 110.16(12)
C8 C9 C10 112.46(13)
N2 C9 H9 109.1(9)
C8 C9 H9 107.7(9)
C10 C9 H9 107.2(9)
C10 N1 C1 123.60(13)
C10 N1 C16 118.96(14)
C1 N1 C16 117.42(13)
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O4 C12 C14 111.56(17)
O4 C12 C15 103.44(12)
C14 C12 C15 110.24(16)
O4 C12 C13 107.72(14)
C14 C12 C13 113.5(2)
C15 C12 C13 109.87(17)
O3 C11 N2 123.82(15)
O3 C11 O4 125.60(15)
N2 C11 O4 110.58(13)
O2 C10 N1 121.58(14)
O2 C10 C9 121.49(13)
N1 C10 C9 116.88(13)
N1 C16 C17 114.23(14)
N1 C16 H16A 108.7
C17 C16 H16A 108.7
N1 C16 H16B 108.7
C17 C16 H16B 108.7
H16A C16 H16B 107.6
C18 C17 C22 118.2(2)
C18 C17 C16 120.63(16)
C22 C17 C16 121.13(19)
C17 C18 C19 121.1(2)
C17 C18 H18 119.5
C19 C18 H18 119.5
C20 C19 C18 119.6(2)
C20 C19 H19 120.2
C18 C19 H19 120.2
C21 C20 C19 120.5(2)
C21 C20 H20 119.8
C19 C20 H20 119.8
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C9 C8 C7 112.84(12)
C9 C8 H8A 105.6(11)
C7 C8 H8A 111.7(11)
C9 C8 H8B 109.9(10)
C7 C8 H8B 108.9(10)
H8A C8 H8B 107.7(15)
C2 C7 C8 116.24(13)
C2 C7 C6 98.71(13)
C8 C7 C6 116.29(14)
C2 C7 H7 107.5(12)
C8 C7 H7 109.8(12)
C6 C7 H7 107.4(12)
C1 C2 C3 126.83(15)
C1 C2 C7 128.70(15)
C3 C2 C7 104.44(14)
C2 C1 N1 124.48(14)
C2 C1 H1 123.0(12)
N1 C1 H1 112.4(12)
C17 C22 C21 120.7(2)
C17 C22 H22 119.7
C21 C22 H22 119.7
C20 C21 C22 120.0(2)
C20 C21 H21 120.0
C22 C21 H21 120.0
O1 C3 C4 101.23(16)
O1 C3 C2 100.66(14)
C4 C3 C2 105.80(13)
O1 C3 H3 111.0(11)
C4 C3 H3 119.3(11)
C2 C3 H3 116.4(11)
C5 C4 C3 105.95(18)
C5 C4 H4 129.5(14)
C3 C4 H4 124.0(14)
C4 C5 C6 105.71(18)
C4 C5 H5 132.3(15)
C6 C5 H5 121.7(15)
O1 C6 C5 101.63(16)
O1 C6 C7 100.88(15)
C5 C6 C7 107.82(14)
O1 C6 H6 111.9(12)
C5 C6 H6 117.0(13)
C7 C6 H6 115.5(13)
C3 O1 C6 95.26(12)
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C11 1.3466(18)
O4 C12 1.4672(18)
N2 C11 1.342(2)
N2 C9 1.4366(19)
N2 H2N 0.836(18)
O2 C10 1.2229(18)
O3 C11 1.2141(19)
C9 C8 1.518(2)
C9 C10 1.542(2)
C9 H9 0.968(16)
N1 C10 1.359(2)
N1 C1 1.413(2)
N1 C16 1.475(2)
C14 C12 1.493(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C12 C15 1.511(2)
C12 C13 1.514(3)
C16 C17 1.501(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.377(3)
C17 C22 1.385(3)
C18 C19 1.384(3)
C18 H18 0.9300
C19 C20 1.372(4)
C19 H19 0.9300
C20 C21 1.358(4)
C20 H20 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C8 C7 1.532(2)
C8 H8A 0.99(2)
C8 H8B 1.001(19)
C7 C2 1.517(2)
C7 C6 1.564(3)
C7 H7 0.97(2)
C2 C1 1.312(2)
C2 C3 1.511(2)
C1 H1 0.92(2)
C22 C21 1.387(4)
C22 H22 0.9300
C21 H21 0.9300
C3 O1 1.439(2)
C3 C4 1.510(3)
C3 H3 1.02(2)
C4 C5 1.312(3)
C4 H4 1.02(3)
C5 C6 1.497(3)
C5 H5 0.97(2)
C6 O1 1.448(2)
C6 H6 0.96(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
