#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:15:42 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059443.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_7059443
loop_
_publ_author_name
'Pan, Zexi'
'Song, Chan'
'Zhou, Wei'
'Cui, Dong-Mei'
'Zhang, Chen'
_publ_section_title
;
 Synthesis of imidazo[1,2-a][1,3,5]triazines by NBS-mediated coupling of
 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6182
_journal_page_last               6185
_journal_paper_doi               10.1039/C9NJ05794C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H17 N5 O2'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-11-25 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                109.818(7)
_cell_angle_beta                 97.305(6)
_cell_angle_gamma                100.110(6)
_cell_formula_units_Z            2
_cell_length_a                   7.1753(5)
_cell_length_b                   10.1901(9)
_cell_length_c                   11.0558(9)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3363
_cell_measurement_theta_min      2.9382
_cell_volume                     733.32(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0264107000
_diffrn_orient_matrix_UB_12      -0.0450985000
_diffrn_orient_matrix_UB_13      0.0348096000
_diffrn_orient_matrix_UB_21      -0.0332988000
_diffrn_orient_matrix_UB_22      0.0552582000
_diffrn_orient_matrix_UB_23      0.0441742000
_diffrn_orient_matrix_UB_31      -0.0932916000
_diffrn_orient_matrix_UB_32      -0.0265533000
_diffrn_orient_matrix_UB_33      -0.0410421000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.944
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0482
_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)+(0.0597P)²+0.1632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2027
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj05794c2.cif
_cod_data_source_block           171130_sc171128
_cod_depositor_comments
;Adding full bibliography for 7059443.cif.

 Adding full bibliography for 7059443.cif.
;
_cod_database_code               7059443
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_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.
;
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.9770(2) 0.71848(16) 0.57390(14) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.81516(19) 0.55909(15) 0.64467(13) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.5101(2) 0.15874(18) 0.40385(16) 0.0284(4) Uani 1 1 d . . . . .
N2 N 0.4419(2) 0.19212(18) 0.19843(16) 0.0278(4) Uani 1 1 d . . . . .
N3 N 0.6298(2) 0.38111(17) 0.39314(15) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.5718(2) 0.42786(18) 0.20952(16) 0.0263(4) Uani 1 1 d . . . . .
N5 N 0.3286(2) -0.02503(18) 0.21569(17) 0.0317(5) Uani 1 1 d . . . . .
C1 C 0.6087(3) 0.2893(2) 0.4593(2) 0.0270(5) Uani 1 1 d . . . . .
H1 H 0.669086 0.323334 0.549313 0.032 Uiso 1 1 calc R . . . .
C2 C 0.4286(3) 0.1118(2) 0.2721(2) 0.0268(5) Uani 1 1 d . . . . .
C3 C 0.5422(3) 0.3281(2) 0.26083(19) 0.0244(5) Uani 1 1 d . . . . .
C4 C 0.7265(3) 0.5254(2) 0.42495(19) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.6831(3) 0.5497(2) 0.30937(19) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.7274(3) 0.6822(2) 0.2805(2) 0.0255(5) Uani 1 1 d . . . . .
C7 C 0.6967(3) 0.6699(2) 0.1495(2) 0.0296(5) Uani 1 1 d . . . . .
H7 H 0.654593 0.577465 0.081839 0.036 Uiso 1 1 calc R . . . .
C8 C 0.7268(3) 0.7906(2) 0.1166(2) 0.0329(5) Uani 1 1 d . . . . .
H8 H 0.704901 0.780650 0.026999 0.040 Uiso 1 1 calc R . . . .
C9 C 0.7889(3) 0.9261(2) 0.2146(2) 0.0325(5) Uani 1 1 d . . . . .
H9 H 0.811942 1.008951 0.192481 0.039 Uiso 1 1 calc R . . . .
C10 C 0.8172(3) 0.9396(2) 0.3445(2) 0.0302(5) Uani 1 1 d . . . . .
H10 H 0.857738 1.032330 0.411837 0.036 Uiso 1 1 calc R . . . .
C11 C 0.7867(3) 0.8190(2) 0.3775(2) 0.0272(5) Uani 1 1 d . . . . .
H11 H 0.806581 0.829866 0.467358 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3059(3) -0.1225(2) 0.2858(2) 0.0348(5) Uani 1 1 d . . . . .
H12A H 0.370068 -0.200203 0.249290 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.168099 -0.162941 0.276457 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.364284 -0.070079 0.378979 0.052 Uiso 1 1 calc GR . . . .
C13 C 0.2487(3) -0.0871(3) 0.0755(2) 0.0426(6) Uani 1 1 d . . . . .
H13A H 0.248059 -0.010127 0.041214 0.064 Uiso 1 1 calc GR . . . .
H13B H 0.116142 -0.143070 0.059780 0.064 Uiso 1 1 calc GR . . . .
H13C H 0.327940 -0.149820 0.030933 0.064 Uiso 1 1 calc GR . . . .
C14 C 0.8519(3) 0.6124(2) 0.5519(2) 0.0263(5) Uani 1 1 d . . . . .
C15 C 0.9357(3) 0.6344(2) 0.77479(19) 0.0292(5) Uani 1 1 d . . . . .
H15A H 0.896799 0.724108 0.820127 0.035 Uiso 1 1 calc R . . . .
H15B H 1.073044 0.659056 0.768653 0.035 Uiso 1 1 calc R . . . .
C16 C 0.9086(3) 0.5358(2) 0.8486(2) 0.0366(6) Uani 1 1 d . . . . .
H16A H 0.951532 0.448800 0.804240 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.771581 0.509848 0.851568 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.984865 0.584126 0.938178 0.055 Uiso 1 1 calc GR . . . .
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
C14 O2 C15 116.82(15) . . ?
C1 N1 C2 117.30(17) . . ?
C2 N2 C3 115.58(17) . . ?
C1 N3 C3 117.73(16) . . ?
C1 N3 C4 135.55(17) . . ?
C3 N3 C4 106.71(15) . . ?
C3 N4 C5 106.03(16) . . ?
C2 N5 C12 123.26(18) . . ?
C2 N5 C13 120.45(17) . . ?
C12 N5 C13 116.12(17) . . ?
N1 C1 N3 122.34(18) . . ?
N1 C1 H1 118.8 . . ?
N3 C1 H1 118.8 . . ?
N2 C2 N1 125.06(18) . . ?
N2 C2 N5 118.49(18) . . ?
N5 C2 N1 116.46(18) . . ?
N2 C3 N3 121.96(17) . . ?
N4 C3 N2 126.52(18) . . ?
N4 C3 N3 111.52(17) . . ?
N3 C4 C14 122.68(17) . . ?
C5 C4 N3 104.23(17) . . ?
C5 C4 C14 132.90(18) . . ?
N4 C5 C4 111.47(17) . . ?
N4 C5 C6 117.34(17) . . ?
C4 C5 C6 131.11(18) . . ?
C7 C6 C5 118.33(19) . . ?
C11 C6 C5 123.28(17) . . ?
C11 C6 C7 118.26(19) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.94(19) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.62(19) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.71(19) . . ?
C10 C11 H11 119.6 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 O2 122.74(19) . . ?
O1 C14 C4 125.45(18) . . ?
O2 C14 C4 111.79(16) . . ?
O2 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
O2 C15 C16 107.04(16) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 C14 1.208(2) . ?
O2 C14 1.346(2) . ?
O2 C15 1.452(2) . ?
N1 C1 1.286(3) . ?
N1 C2 1.380(3) . ?
N2 C2 1.337(2) . ?
N2 C3 1.338(2) . ?
N3 C1 1.369(2) . ?
N3 C3 1.392(2) . ?
N3 C4 1.413(2) . ?
N4 C3 1.321(2) . ?
N4 C5 1.377(3) . ?
N5 C2 1.339(3) . ?
N5 C12 1.453(3) . ?
N5 C13 1.454(3) . ?
C1 H1 0.9500 . ?
C4 C5 1.390(3) . ?
C4 C14 1.456(3) . ?
C5 C6 1.481(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.497(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
