#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:05:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180247 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/33/7113300.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_7113300
loop_
_publ_author_name
'Boltjes, André'
'Liao, George P.'
'Zhao, Ting'
'Herdtweck, Eberhardt'
'Dömling, Alexander'
_publ_section_title
;
 Ugi 4-CR Synthesis of γ- and δ-Lactams providing new access to diverse
 enzyme interactions, a PDB analysis.
;
_journal_issue                   7
_journal_name_full               MedChemComm
_journal_page_first              949
_journal_page_last               952
_journal_paper_doi               10.1039/C4MD00162A
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C11 H17 N5 O'
_chemical_formula_sum            'C11 H17 N5 O'
_chemical_formula_weight         235.30
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                65.9412(10)
_cell_angle_beta                 81.5752(11)
_cell_angle_gamma                89.9391(11)
_cell_formula_units_Z            2
_cell_length_a                   6.5462(2)
_cell_length_b                   9.2570(2)
_cell_length_c                   10.5529(3)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.14
_cell_volume                     576.41(3)
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_molecular_graphics    'PLATON (Spek, 2010)'
_computing_publication_material  'PLATON (Spek, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19536
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       fragment
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0303
_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)+(0.0400P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                2033
_reflns_number_total             2111
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4md00162a2.cif
_cod_data_source_block           compound_6e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7113299--7113302.cif.

 Adding full bibliography for 7113299--7113302.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_database_code               7113300
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
O1 O Uani -0.19947(11) -0.12238(9) 0.47110(8) 1.000 0.0187(2)
N1 N Uani 0.45115(13) 0.14746(10) 0.12345(9) 1.000 0.0129(2)
N2 N Uani 0.43085(13) 0.24291(10) -0.01008(9) 1.000 0.0152(2)
N3 N Uani 0.30930(13) 0.16472(11) -0.05026(9) 1.000 0.0162(2)
N4 N Uani 0.24877(13) 0.01897(10) 0.05423(9) 1.000 0.0153(2)
N5 N Uani 0.15168(13) -0.08949(10) 0.39941(9) 1.000 0.0144(3)
C1 C Uani 0.33900(15) 0.01069(12) 0.16085(11) 1.000 0.0129(3)
C2 C Uani 0.30818(16) -0.12549(12) 0.30383(11) 1.000 0.0143(3)
C3 C Uani -0.03940(16) -0.15067(12) 0.40970(10) 1.000 0.0149(3)
C4 C Uani -0.02484(17) -0.25836(13) 0.33341(12) 1.000 0.0181(3)
C5 C Uani 0.20772(17) -0.27603(12) 0.30321(12) 1.000 0.0173(3)
C6 C Uani 0.58675(16) 0.19938(12) 0.19901(11) 1.000 0.0138(3)
C7 C Uani 0.50258(16) 0.34137(12) 0.22390(11) 1.000 0.0150(3)
C8 C Uani 0.64586(17) 0.39371(13) 0.30170(12) 1.000 0.0183(3)
C9 C Uani 0.86832(17) 0.42935(13) 0.22386(12) 1.000 0.0190(3)
C10 C Uani 0.94855(17) 0.28975(13) 0.19427(12) 1.000 0.0187(3)
C11 C Uani 0.80598(16) 0.23728(14) 0.11675(12) 1.000 0.0184(3)
H5 H Uiso 0.175(2) -0.0209(18) 0.4333(15) 1.000 0.029(4)
H21 H Uiso 0.4397(19) -0.1443(14) 0.3401(13) 1.000 0.014(3)
H41 H Uiso -0.083(2) -0.2067(16) 0.2483(15) 1.000 0.022(3)
H42 H Uiso -0.103(2) -0.3564(16) 0.3920(14) 1.000 0.020(3)
H51 H Uiso 0.2521(19) -0.2843(15) 0.2155(14) 1.000 0.018(3)
H52 H Uiso 0.2494(19) -0.3689(15) 0.3791(14) 1.000 0.017(3)
H61 H Uiso 0.5840(18) 0.1087(14) 0.2886(13) 1.000 0.012(3)
H71 H Uiso 0.362(2) 0.3127(15) 0.2783(14) 1.000 0.019(3)
H72 H Uiso 0.4964(19) 0.4298(15) 0.1329(14) 1.000 0.015(3)
H81 H Uiso 0.593(2) 0.4879(17) 0.3130(15) 1.000 0.027(4)
H82 H Uiso 0.642(2) 0.3089(16) 0.3958(15) 1.000 0.022(3)
H91 H Uiso 0.873(2) 0.5234(17) 0.1353(15) 1.000 0.022(3)
H92 H Uiso 0.959(2) 0.4559(16) 0.2780(14) 1.000 0.025(3)
H101 H Uiso 0.959(2) 0.1983(16) 0.2837(15) 1.000 0.022(3)
H102 H Uiso 1.088(2) 0.3192(15) 0.1370(14) 1.000 0.021(3)
H111 H Uiso 0.802(2) 0.3230(16) 0.0244(15) 1.000 0.022(3)
H112 H Uiso 0.854(2) 0.1449(17) 0.1003(15) 1.000 0.026(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_publ_flag
N2 N1 C1 108.11(9) yes
N2 N1 C6 120.26(9) yes
C1 N1 C6 131.57(9) yes
N1 N2 N3 106.52(9) yes
N2 N3 N4 110.86(8) yes
N3 N4 C1 105.68(9) yes
C2 N5 C3 113.41(9) yes
C2 N5 H5 123.0(9) no
C3 N5 H5 122.6(9) no
N1 C1 N4 108.83(9) yes
N1 C1 C2 125.85(9) yes
N4 C1 C2 125.19(10) yes
N5 C2 C1 109.59(9) yes
C1 C2 C5 112.28(9) no
N5 C2 C5 101.88(9) yes
O1 C3 C4 126.05(10) yes
N5 C3 C4 108.66(9) yes
O1 C3 N5 125.29(11) yes
C3 C4 C5 104.06(9) no
C2 C5 C4 103.76(9) no
N1 C6 C7 110.82(9) yes
C7 C6 C11 111.60(10) no
N1 C6 C11 109.49(9) yes
C6 C7 C8 109.96(9) no
C7 C8 C9 111.67(9) no
C8 C9 C10 111.52(10) no
C9 C10 C11 111.89(10) no
C6 C11 C10 110.11(10) no
N5 C2 H21 110.5(8) no
C1 C2 H21 109.7(7) no
C5 C2 H21 112.6(8) no
C3 C4 H41 108.0(10) no
C3 C4 H42 109.1(9) no
C5 C4 H41 112.1(8) no
C5 C4 H42 113.7(9) no
H41 C4 H42 109.5(12) no
C2 C5 H51 111.2(9) no
C2 C5 H52 108.7(8) no
C4 C5 H51 114.1(8) no
C4 C5 H52 110.5(8) no
H51 C5 H52 108.6(12) no
N1 C6 H61 104.8(8) no
C7 C6 H61 109.8(8) no
C11 C6 H61 110.1(7) no
C6 C7 H71 109.6(9) no
C6 C7 H72 109.2(9) no
C8 C7 H71 110.6(8) no
C8 C7 H72 108.7(8) no
H71 C7 H72 108.8(11) no
C7 C8 H81 108.9(8) no
C7 C8 H82 108.6(9) no
C9 C8 H81 110.3(8) no
C9 C8 H82 109.6(8) no
H81 C8 H82 107.7(12) no
C8 C9 H91 108.7(8) no
C8 C9 H92 110.5(8) no
C10 C9 H91 109.9(9) no
C10 C9 H92 109.7(9) no
H91 C9 H92 106.4(12) no
C9 C10 H101 110.0(9) no
C9 C10 H102 109.8(9) no
C11 C10 H101 108.0(9) no
C11 C10 H102 108.9(8) no
H101 C10 H102 108.2(11) no
C6 C11 H111 108.2(8) no
C6 C11 H112 109.6(8) no
C10 C11 H111 109.6(9) no
C10 C11 H112 112.4(8) no
H111 C11 H112 106.8(12) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.2350(13) yes
N1 N2 1.3504(12) yes
N1 C1 1.3444(15) yes
N1 C6 1.4750(14) yes
N2 N3 1.2989(14) yes
N3 N4 1.3614(13) yes
N4 C1 1.3210(14) yes
N5 C2 1.4658(14) yes
N5 C3 1.3449(14) yes
N5 H5 0.869(17) no
C1 C2 1.5057(15) no
C2 C5 1.5444(17) no
C3 C4 1.5109(17) no
C4 C5 1.5316(16) no
C6 C11 1.5245(15) no
C6 C7 1.5290(17) no
C7 C8 1.5295(16) no
C8 C9 1.5277(16) no
C9 C10 1.5241(18) no
C10 C11 1.5247(17) no
C2 H21 0.980(13) no
C4 H41 0.964(14) no
C4 H42 0.958(15) no
C5 H51 0.962(14) no
C5 H52 0.978(14) no
C6 H61 0.973(13) no
C7 H71 0.984(13) no
C7 H72 0.982(14) no
C8 H81 0.983(17) no
C8 H82 0.980(15) no
C9 H91 0.980(15) no
C9 H92 0.976(14) no
C10 H101 0.990(15) no
C10 H102 0.989(13) no
C11 H111 0.978(15) no
C11 H112 0.982(17) no
