#------------------------------------------------------------------------------
#$Date: 2019-11-24 20:35:05 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/60/1556035.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_1556035
loop_
_publ_author_name
'Foley, Christopher'
'Shaw, Arthur'
'Hulme, Christopher'
_publ_section_title
;
 Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR
 Products: A Two-Step MCR-Oxidation Protocol toward Functionalized
 α-Ketoamides and α-Ketotetrazoles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2238
_journal_page_last               2241
_journal_paper_doi               10.1021/acs.orglett.7b00710
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H16 N4 O'
_chemical_formula_sum            'C14 H16 N4 O'
_chemical_formula_weight         256.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7378(3)
_cell_length_b                   6.7075(2)
_cell_length_c                   12.6395(5)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.69
_cell_volume                     640.89(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7085
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         1.649
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.9022.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0331
_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)+(0.0459P)²+0.2367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1474
_reflns_number_total             1524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00710_si_003.cif
_cod_data_source_block           mo_cf376f1_0m
_cod_database_code               1556035
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H14c(0.5) H14b(0.5) H14a(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C1(H1), C5(H5), C4(H4), C2(H2), C3(H3)
3.b Idealised Me refined as rotating group:
 C13(H13b,H13c,H13a), C14(H14c,H14b,H14a)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id cf371.f1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49113(12) 0.7500 0.64661(7) 0.0174(2) Uani 1 2 d S T P . .
N4 N 0.56397(13) 0.7500 0.88807(8) 0.0114(2) Uani 1 2 d S T P . .
N1 N 0.27691(14) 0.7500 0.87016(9) 0.0151(2) Uani 1 2 d S T P . .
N3 N 0.52853(14) 0.7500 0.98799(8) 0.0142(2) Uani 1 2 d S T P . .
N2 N 0.35729(14) 0.7500 0.97626(9) 0.0163(2) Uani 1 2 d S T P . .
C8 C 0.18242(16) 0.7500 0.63909(10) 0.0138(3) Uani 1 2 d S T P . .
H8 H 0.0921 0.7500 0.6796 0.017 Uiso 1 2 calc RS T P . .
C9 C 0.37010(16) 0.7500 0.69429(10) 0.0130(3) Uani 1 2 d S T P . .
C6 C -0.03484(16) 0.7500 0.45963(10) 0.0126(3) Uani 1 2 d S T P . .
C10 C 0.40579(16) 0.7500 0.81580(10) 0.0125(3) Uani 1 2 d S T P . .
C11 C 0.75458(15) 0.7500 0.87653(9) 0.0118(3) Uani 1 2 d S T P . .
C7 C 0.14125(16) 0.7500 0.53061(10) 0.0134(3) Uani 1 2 d S T P . .
H7 H 0.2383 0.7500 0.4955 0.016 Uiso 1 2 calc RS T P . .
C1 C -0.19097(17) 0.7500 0.49873(10) 0.0151(3) Uani 1 2 d S T P . .
H1 H -0.1849 0.7500 0.5746 0.018 Uiso 1 2 calc RS T P . .
C5 C -0.04695(17) 0.7500 0.34740(10) 0.0145(3) Uani 1 2 d S T P . .
H5 H 0.0580 0.7500 0.3198 0.017 Uiso 1 2 calc RS T P . .
C13 C 0.78870(11) 0.55993(14) 0.81720(7) 0.0147(2) Uani 1 1 d . . . . .
H13B H 0.7619 0.4432 0.8575 0.022 Uiso 1 1 calc GR . . . .
H13C H 0.9131 0.5557 0.8118 0.022 Uiso 1 1 calc GR . . . .
H13A H 0.7130 0.5592 0.7444 0.022 Uiso 1 1 calc GR . . . .
C4 C -0.21110(18) 0.7500 0.27600(10) 0.0168(3) Uani 1 2 d S T P . .
H4 H -0.2179 0.7500 0.2001 0.020 Uiso 1 2 calc RS T P . .
C2 C -0.35486(17) 0.7500 0.42739(11) 0.0172(3) Uani 1 2 d S T P . .
H2 H -0.4603 0.7500 0.4545 0.021 Uiso 1 2 calc RS T P . .
C14 C 0.87251(16) 0.7500 0.99008(10) 0.0153(3) Uani 1 2 d S T P . .
H14C H 0.8515 0.8719 1.0282 0.023 Uiso 0.5 1 calc GR . . A -1
H14B H 0.9969 0.7447 0.9847 0.023 Uiso 0.5 1 calc GR . . A -1
H14A H 0.8448 0.6334 1.0302 0.023 Uiso 0.5 1 calc GR . . A -1
C3 C -0.36444(17) 0.7500 0.31596(10) 0.0168(3) Uani 1 2 d S T P . .
H3 H -0.4765 0.7500 0.2673 0.020 Uiso 1 2 calc RS T P . .
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_3
N3 N4 C10 107.15(10) .
N3 N4 C11 119.19(10) .
C10 N4 C11 133.65(10) .
C10 N1 N2 106.03(10) .
N2 N3 N4 107.40(10) .
N3 N2 N1 110.76(10) .
C9 C8 H8 120.6 .
C7 C8 H8 120.6 .
C7 C8 C9 118.72(11) .
O1 C9 C8 123.46(11) .
O1 C9 C10 120.90(11) .
C8 C9 C10 115.64(11) .
C1 C6 C7 123.01(11) .
C1 C6 C5 118.75(11) .
C5 C6 C7 118.24(11) .
N4 C10 C9 128.96(11) .
N1 C10 N4 108.66(11) .
N1 C10 C9 122.38(11) .
N4 C11 C13 108.72(6) 4_575
N4 C11 C13 108.72(6) .
N4 C11 C14 107.97(9) .
C13 C11 C13 112.84(10) 4_575
C14 C11 C13 109.24(6) 4_575
C14 C11 C13 109.23(6) .
C8 C7 C6 127.92(11) .
C8 C7 H7 116.0 .
C6 C7 H7 116.0 .
C6 C1 H1 119.7 .
C2 C1 C6 120.51(11) .
C2 C1 H1 119.7 .
C6 C5 H5 119.6 .
C4 C5 C6 120.72(12) .
C4 C5 H5 119.6 .
C11 C13 H13B 109.5 .
C11 C13 H13C 109.5 .
C11 C13 H13A 109.5 .
H13B C13 H13C 109.5 .
H13B C13 H13A 109.5 .
H13C C13 H13A 109.5 .
C5 C4 H4 120.1 .
C3 C4 C5 119.84(12) .
C3 C4 H4 120.1 .
C1 C2 H2 120.0 .
C1 C2 C3 119.97(12) .
C3 C2 H2 120.0 .
C11 C14 H14C 109.5 .
C11 C14 H14B 109.5 .
C11 C14 H14A 109.5 .
H14C C14 H14B 109.5 .
H14C C14 H14A 109.5 .
H14B C14 H14A 109.5 .
C4 C3 C2 120.21(12) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.2170(15) .
N4 N3 1.3483(14) .
N4 C10 1.3621(15) .
N4 C11 1.5128(15) .
N1 N2 1.3525(15) .
N1 C10 1.3263(16) .
N3 N2 1.3015(15) .
C8 H8 0.9500 .
C8 C9 1.4709(17) .
C8 C7 1.3398(17) .
C9 C10 1.5013(17) .
C6 C7 1.4627(16) .
C6 C1 1.3995(17) .
C6 C5 1.4015(16) .
C11 C13 1.5303(11) .
C11 C13 1.5303(11) 4_575
C11 C14 1.5277(16) .
C7 H7 0.9500 .
C1 H1 0.9500 .
C1 C2 1.3904(17) .
C5 H5 0.9500 .
C5 C4 1.3923(18) .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C13 H13A 0.9800 .
C4 H4 0.9500 .
C4 C3 1.3853(19) .
C2 H2 0.9500 .
C2 C3 1.3944(18) .
C14 H14C 0.9800 .
C14 H14B 0.9800 .
C14 H14A 0.9800 .
C3 H3 0.9500 .
