#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:08:19 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226662 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/51/4035185.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_4035185
loop_
_publ_author_name
'Yokoi, Taiki'
'Tanimoto, Hiroki'
'Ueda, Tomomi'
'Morimoto, Tsumoru'
'Kakiuchi, Kiyomi'
_publ_section_title
;
 Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to
 Diazo Groups in Diazido and Triazido Compounds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12103
_journal_page_last               12121
_journal_paper_doi               10.1021/acs.joc.8b02074
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 N6 O2'
_chemical_formula_sum            'C17 H14 N6 O2'
_chemical_formula_weight         334.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   8.17797(15)
_cell_length_b                   14.6247(3)
_cell_length_c                   27.2033(5)
_cell_measurement_reflns_used    39936
_cell_measurement_temperature    103
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.60
_cell_volume                     3253.52(11)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            52120
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.786
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392.00
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0395P)²+1.5993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3304
_reflns_number_total             3740
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo8b02074_si_003.cif
_cod_data_source_block           TY_09_055_02
_cod_original_cell_volume        3253.52(10)
_cod_database_code               4035185
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+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
O1 O 1.00235(10) 0.58600(5) 0.38620(3) 0.02043(18) Uani 1 1 d . .
O2 O 0.05884(10) 0.81443(6) 0.40408(4) 0.0264(2) Uani 1 1 d . .
N1 N 0.77417(11) 0.65929(6) 0.36067(3) 0.0155(2) Uani 1 1 d . .
N2 N 0.93867(13) 0.60458(7) 0.48375(4) 0.0247(2) Uani 1 1 d . .
N3 N 1.08691(13) 0.62194(7) 0.48472(4) 0.0231(2) Uani 1 1 d . .
N4 N 1.22315(14) 0.63122(9) 0.49011(4) 0.0322(3) Uani 1 1 d . .
N5 N 0.05681(13) 0.98570(7) 0.43269(4) 0.0213(2) Uani 1 1 d . .
N6 N -0.06609(14) 1.00911(8) 0.44540(4) 0.0291(3) Uani 1 1 d . .
C1 C 0.88097(13) 0.63175(7) 0.39593(4) 0.0159(2) Uani 1 1 d . .
C2 C 0.84524(14) 0.66077(8) 0.44882(4) 0.0180(2) Uani 1 1 d . .
H2A H 0.874701 0.725920 0.453197 0.022 Uiso 1 1 calc R U
H2B H 0.726863 0.654125 0.455555 0.022 Uiso 1 1 calc R U
C3 C 0.62876(13) 0.71092(7) 0.37104(4) 0.0150(2) Uani 1 1 d . .
C4 C 0.64019(13) 0.79984(7) 0.38885(4) 0.0163(2) Uani 1 1 d . .
H4 H 0.744380 0.826876 0.394084 0.020 Uiso 1 1 calc R U
C5 C 0.49900(14) 0.84893(8) 0.39896(4) 0.0163(2) Uani 1 1 d . .
H5 H 0.506645 0.909616 0.411207 0.020 Uiso 1 1 calc R U
C6 C 0.34581(13) 0.80952(7) 0.39121(4) 0.0158(2) Uani 1 1 d . .
C7 C 0.33558(14) 0.72092(8) 0.37225(4) 0.0190(2) Uani 1 1 d . .
H7 H 0.231557 0.694078 0.366468 0.023 Uiso 1 1 calc R U
C8 C 0.47634(14) 0.67210(8) 0.36185(4) 0.0185(2) Uani 1 1 d . .
H8 H 0.468986 0.612240 0.348476 0.022 Uiso 1 1 calc R U
C9 C 0.18917(14) 0.85631(8) 0.40412(4) 0.0176(2) Uani 1 1 d . .
C10 C 0.19689(14) 0.95186(8) 0.41710(5) 0.0209(2) Uani 1 1 d . .
H10 H 0.294056 0.987164 0.414641 0.025 Uiso 1 1 calc R U
C11 C 0.81100(14) 0.63947(8) 0.30881(4) 0.0185(2) Uani 1 1 d . .
H11A H 0.930941 0.633168 0.305215 0.022 Uiso 1 1 calc R U
H11B H 0.776626 0.692585 0.288749 0.022 Uiso 1 1 calc R U
C12 C 0.73079(14) 0.55444(8) 0.28806(4) 0.0174(2) Uani 1 1 d . .
C13 C 0.70394(15) 0.54968(9) 0.23752(4) 0.0227(3) Uani 1 1 d . .
H13 H 0.733684 0.599864 0.217223 0.027 Uiso 1 1 calc R U
C14 C 0.63438(17) 0.47262(9) 0.21655(5) 0.0283(3) Uani 1 1 d . .
H14 H 0.617613 0.470101 0.182019 0.034 Uiso 1 1 calc R U
C15 C 0.58923(16) 0.39927(9) 0.24570(5) 0.0270(3) Uani 1 1 d . .
H15 H 0.540737 0.346654 0.231314 0.032 Uiso 1 1 calc R U
C16 C 0.61527(15) 0.40310(8) 0.29612(5) 0.0238(3) Uani 1 1 d . .
H16 H 0.584169 0.353101 0.316361 0.029 Uiso 1 1 calc R U
C17 C 0.68693(15) 0.48020(8) 0.31697(4) 0.0203(2) Uani 1 1 d . .
H17 H 0.706043 0.482040 0.351404 0.024 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C1 N1 C3 123.33(9)
C1 N1 C11 119.14(9)
C3 N1 C11 117.47(9)
N3 N2 C2 114.06(10)
N4 N3 N2 172.10(13)
N6 N5 C10 175.62(12)
O1 C1 N1 122.01(10)
O1 C1 C2 120.64(10)
N1 C1 C2 117.35(9)
N2 C2 C1 110.72(9)
N2 C2 H2A 109.5
C1 C2 H2A 109.5
N2 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
C4 C3 C8 120.26(10)
C4 C3 N1 120.28(10)
C8 C3 N1 119.45(10)
C5 C4 C3 119.80(10)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.24(10)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C7 119.53(10)
C5 C6 C9 123.03(10)
C7 C6 C9 117.40(10)
C8 C7 C6 120.27(10)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C3 119.85(10)
C7 C8 H8 120.1
C3 C8 H8 120.1
O2 C9 C10 121.38(10)
O2 C9 C6 121.00(10)
C10 C9 C6 117.62(10)
N5 C10 C9 113.85(11)
N5 C10 H10 123.1
C9 C10 H10 123.1
N1 C11 C12 115.48(9)
N1 C11 H11A 108.4
C12 C11 H11A 108.4
N1 C11 H11B 108.4
C12 C11 H11B 108.4
H11A C11 H11B 107.5
C17 C12 C13 118.63(11)
C17 C12 C11 122.89(10)
C13 C12 C11 118.46(10)
C14 C13 C12 120.75(12)
C14 C13 H13 119.6
C12 C13 H13 119.6
C15 C14 C13 120.28(12)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 119.57(12)
C14 C15 H15 120.2
C16 C15 H15 120.2
C15 C16 C17 119.98(12)
C15 C16 H16 120.0
C17 C16 H16 120.0
C12 C17 C16 120.78(11)
C12 C17 H17 119.6
C16 C17 H17 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2259(13)
O2 C9 1.2292(14)
N1 C1 1.3584(15)
N1 C3 1.4365(14)
N1 C11 1.4715(14)
N2 N3 1.2390(15)
N2 C2 1.4703(15)
N3 N4 1.1319(15)
N5 N6 1.1167(15)
N5 C10 1.3179(15)
C1 C2 1.5284(16)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.3910(15)
C3 C8 1.3923(15)
C4 C5 1.3872(15)
C4 H4 0.9500
C5 C6 1.3951(15)
C5 H5 0.9500
C6 C7 1.3971(16)
C6 C9 1.4942(15)
C7 C8 1.3837(16)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.4428(16)
C10 H10 0.9500
C11 C12 1.5150(16)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C17 1.3878(16)
C12 C13 1.3941(16)
C13 C14 1.3854(18)
C13 H13 0.9500
C14 C15 1.3840(19)
C14 H14 0.9500
C15 C16 1.3893(18)
C15 H15 0.9500
C16 C17 1.3916(17)
C16 H16 0.9500
C17 H17 0.9500
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
C3 N1 C1 O1 178.36(10)
C11 N1 C1 O1 -4.51(16)
C3 N1 C1 C2 -2.18(15)
C11 N1 C1 C2 174.95(9)
N3 N2 C2 C1 72.68(13)
O1 C1 C2 N2 -17.72(14)
N1 C1 C2 N2 162.81(10)
C1 N1 C3 C4 66.39(14)
C11 N1 C3 C4 -110.78(12)
C1 N1 C3 C8 -115.34(12)
C11 N1 C3 C8 67.48(13)
C8 C3 C4 C5 2.05(17)
N1 C3 C4 C5 -179.70(10)
C3 C4 C5 C6 -0.16(16)
C4 C5 C6 C7 -1.30(16)
C4 C5 C6 C9 176.21(11)
C5 C6 C7 C8 0.88(17)
C9 C6 C7 C8 -176.77(10)
C6 C7 C8 C3 1.00(17)
C4 C3 C8 C7 -2.47(17)
N1 C3 C8 C7 179.27(10)
C5 C6 C9 O2 -168.37(11)
C7 C6 C9 O2 9.18(16)
C5 C6 C9 C10 10.98(16)
C7 C6 C9 C10 -171.46(11)
O2 C9 C10 N5 5.76(17)
C6 C9 C10 N5 -173.59(10)
C1 N1 C11 C12 96.45(12)
C3 N1 C11 C12 -86.26(12)
N1 C11 C12 C17 -26.95(16)
N1 C11 C12 C13 154.82(10)
C17 C12 C13 C14 0.23(18)
C11 C12 C13 C14 178.54(11)
C12 C13 C14 C15 0.52(19)
C13 C14 C15 C16 -0.5(2)
C14 C15 C16 C17 -0.25(19)
C13 C12 C17 C16 -0.99(17)
C11 C12 C17 C16 -179.22(11)
C15 C16 C17 C12 1.01(18)
