#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:05:04 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126411.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_7126411
loop_
_publ_author_name
'Wang, Ya'
'Zhou, Yao'
'Song, Qiuling'
_publ_section_title
;
 [3+1+1] type cyclization of ClCF₂COONa for the assembly of
 imidazoles and tetrazoles via in situ generated isocyanides.
;
_journal_issue                   45
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6106
_journal_page_last               6109
_journal_paper_doi               10.1039/d0cc01919d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C8 H8 N4'
_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_weight         160.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.261(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7747(9)
_cell_length_b                   5.6834(5)
_cell_length_c                   14.3307(13)
_cell_measurement_reflns_used    948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5660
_cell_measurement_theta_min      4.5500
_cell_volume                     791.37(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  83.00   1.00    5.70    --   15.65  57.00 150.00   50
  2  ω     26.00  82.00   1.00    5.70    --   15.65  77.00 -90.00   56
  3  ω    -14.00  84.00   1.00    5.70    --   15.65  19.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0364810000
_diffrn_orient_matrix_UB_12      0.0843325000
_diffrn_orient_matrix_UB_13      0.0296007000
_diffrn_orient_matrix_UB_21      -0.0521910000
_diffrn_orient_matrix_UB_22      -0.0039698000
_diffrn_orient_matrix_UB_23      0.0306732000
_diffrn_orient_matrix_UB_31      0.0356960000
_diffrn_orient_matrix_UB_32      -0.0918392000
_diffrn_orient_matrix_UB_33      0.0257843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.142
_diffrn_reflns_theta_min         3.860
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0483
_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)+(0.0713P)²+0.0353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1174
_reflns_number_total             1834
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01919d2.cif
_cod_data_source_block           exp_7025
_cod_depositor_comments
'Adding full bibliography for 7126410--7126412.cif.'
_cod_database_code               7126411
_shelx_shelxl_version_number     2018/3
_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   0.991
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.671
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
N1 N 0.81100(17) 0.7570(3) 0.35260(11) 0.0779(5) Uani 1 1 d . . . . .
N2 N 0.75038(18) 0.5563(3) 0.37474(13) 0.0826(5) Uani 1 1 d . . . . .
N3 N 0.62342(17) 0.5905(3) 0.38487(12) 0.0789(5) Uani 1 1 d . . . . .
N4 N 0.59807(13) 0.8191(2) 0.36842(9) 0.0532(4) Uani 1 1 d . . . . .
C1 C 0.71516(17) 0.9151(3) 0.35010(12) 0.0677(5) Uani 1 1 d . . . . .
H1 H 0.727166 1.073650 0.337224 0.081 Uiso 1 1 calc R . . . .
C2 C 0.46532(15) 0.9187(3) 0.37333(10) 0.0500(4) Uani 1 1 d . . . . .
C3 C 0.37345(17) 0.8065(3) 0.42367(11) 0.0596(5) Uani 1 1 d . . . . .
H3 H 0.396951 0.665997 0.454596 0.072 Uiso 1 1 calc R . . . .
C4 C 0.24624(17) 0.9050(3) 0.42767(12) 0.0642(5) Uani 1 1 d . . . . .
H4 H 0.183129 0.827982 0.461027 0.077 Uiso 1 1 calc R . . . .
C5 C 0.20914(16) 1.1141(3) 0.38388(11) 0.0589(5) Uani 1 1 d . . . . .
C6 C 0.30417(18) 1.2218(3) 0.33356(12) 0.0606(5) Uani 1 1 d . . . . .
H6 H 0.281494 1.363437 0.303274 0.073 Uiso 1 1 calc R . . . .
C7 C 0.43128(16) 1.1248(3) 0.32717(11) 0.0557(4) Uani 1 1 d . . . . .
H7 H 0.493479 1.198084 0.291943 0.067 Uiso 1 1 calc R . . . .
C8 C 0.0706(2) 1.2223(4) 0.38998(15) 0.0832(6) Uani 1 1 d . . . . .
H8A H 0.000639 1.123008 0.358595 0.125 Uiso 1 1 calc GR . . . .
H8B H 0.067047 1.374281 0.360546 0.125 Uiso 1 1 calc GR . . . .
H8C H 0.055381 1.239081 0.454700 0.125 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'
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
C1 N1 N2 105.06(15) . . ?
N3 N2 N1 110.91(14) . . ?
N2 N3 N4 106.89(14) . . ?
N3 N4 C2 121.94(13) . . ?
C1 N4 N3 106.75(14) . . ?
C1 N4 C2 131.30(14) . . ?
N1 C1 N4 110.38(16) . . ?
N1 C1 H1 124.8 . . ?
N4 C1 H1 124.8 . . ?
C3 C2 N4 119.62(15) . . ?
C7 C2 N4 119.41(14) . . ?
C7 C2 C3 120.96(15) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.82(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.97(15) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.59(16) . . ?
C4 C5 C8 121.57(16) . . ?
C6 C5 C8 120.84(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.55(16) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 119.08(15) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
N1 N2 1.340(2) . ?
N1 C1 1.295(2) . ?
N2 N3 1.280(2) . ?
N3 N4 1.3389(19) . ?
N4 C1 1.3198(19) . ?
N4 C2 1.4245(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(2) . ?
C2 C7 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(2) . ?
C5 C6 1.380(2) . ?
C5 C8 1.499(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 0.5(2) . . . . ?
N2 N1 C1 N4 -0.9(2) . . . . ?
N2 N3 N4 C1 -1.02(19) . . . . ?
N2 N3 N4 C2 179.76(14) . . . . ?
N3 N4 C1 N1 1.21(19) . . . . ?
N3 N4 C2 C3 21.4(2) . . . . ?
N3 N4 C2 C7 -158.26(15) . . . . ?
N4 C2 C3 C4 179.96(13) . . . . ?
N4 C2 C7 C6 -178.87(13) . . . . ?
C1 N1 N2 N3 0.2(2) . . . . ?
C1 N4 C2 C3 -157.61(16) . . . . ?
C1 N4 C2 C7 22.7(2) . . . . ?
C2 N4 C1 N1 -179.67(15) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C2 C7 C6 1.5(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.98(16) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C7 C2 C3 C4 -0.4(2) . . . . ?
C8 C5 C6 C7 -179.89(15) . . . . ?
