#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:05:04 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126410.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_7126410
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         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2019-05-21 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.85(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.722(4)
_cell_length_b                   7.3514(16)
_cell_length_c                   20.934(4)
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8300
_cell_measurement_theta_min      3.9950
_cell_volume                     2509.0(10)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  51.00   1.00    7.50    --  -16.28  38.00  60.00   83
  2  ω    -14.00  31.00   1.00    7.50    --   15.49 -99.00 -30.00   45
  3  ω    -22.00  21.00   1.00    7.50    --  -16.28 -99.00  60.00   43
  4  ω    -23.00  23.00   1.00    7.50    --  -16.28 -99.00-150.00   46
;
_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      -0.0418124000
_diffrn_orient_matrix_UB_12      -0.0185763000
_diffrn_orient_matrix_UB_13      -0.0141698000
_diffrn_orient_matrix_UB_21      -0.0120342000
_diffrn_orient_matrix_UB_22      0.0638675000
_diffrn_orient_matrix_UB_23      0.0215082000
_diffrn_orient_matrix_UB_31      0.0000101000
_diffrn_orient_matrix_UB_32      0.0701657000
_diffrn_orient_matrix_UB_33      -0.0231996000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4649
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.481
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49630
_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_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0487
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1614
_reflns_number_total             2199
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01919d2.cif
_cod_data_source_block           exp_6811
_cod_depositor_comments
'Adding full bibliography for 7126410--7126412.cif.'
_cod_original_cell_volume        2509.1(10)
_cod_database_code               7126410
_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.
;
_reflns_odcompleteness_completeness 99.42
_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:
 C00F(H00C,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00G(H00G,H00H,H00I), C00H(H00J,H00K,H00L)
;
_shelx_shelxl_version_number     2014/7
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.391
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
O001 O 0.59961(8) -0.20071(16) 0.35785(6) 0.0562(4) Uani 1 1 d . . . . .
N002 N 0.46063(8) 0.31798(18) 0.36373(6) 0.0462(4) Uani 1 1 d . . . . .
O003 O 0.57671(10) -0.15375(19) 0.45728(7) 0.0812(5) Uani 1 1 d . . . . .
N004 N 0.52157(10) 0.1158(2) 0.31118(7) 0.0618(5) Uani 1 1 d . . . . .
C005 C 0.41684(10) 0.4785(2) 0.37510(8) 0.0458(4) Uani 1 1 d . . . . .
C006 C 0.52848(10) 0.0618(2) 0.37449(7) 0.0457(4) Uani 1 1 d . . . . .
C007 C 0.56994(10) -0.1061(2) 0.40166(8) 0.0505(5) Uani 1 1 d . . . . .
C008 C 0.49184(10) 0.1834(2) 0.40719(8) 0.0505(5) Uani 1 1 d . . . . .
H008 H 0.4885 0.1767 0.4509 0.061 Uiso 1 1 calc R . . . .
C009 C 0.48064(13) 0.2693(3) 0.30679(8) 0.0641(6) Uani 1 1 d . . . . .
H009 H 0.4668 0.3377 0.2686 0.077 Uiso 1 1 calc R . . . .
C00A C 0.39701(13) 0.6104(3) 0.32745(10) 0.0651(6) Uani 1 1 d . . . . .
H00A H 0.4117 0.5956 0.2874 0.078 Uiso 1 1 calc R . . . .
C00B C 0.39444(12) 0.5035(3) 0.43391(9) 0.0638(6) Uani 1 1 d . . . . .
H00B H 0.4073 0.4158 0.4666 0.077 Uiso 1 1 calc R . . . .
C00C C 0.33222(12) 0.7930(3) 0.39693(11) 0.0629(6) Uani 1 1 d . . . . .
C00D C 0.35263(12) 0.6596(3) 0.44420(10) 0.0701(6) Uani 1 1 d . . . . .
H00D H 0.3378 0.6750 0.4841 0.084 Uiso 1 1 calc R . . . .
C00E C 0.35533(13) 0.7643(3) 0.33919(11) 0.0705(6) Uani 1 1 d . . . . .
H00E H 0.3425 0.8520 0.3065 0.085 Uiso 1 1 calc R . . . .
C00F C 0.64311(13) -0.3674(3) 0.38120(11) 0.0725(6) Uani 1 1 d . . . . .
H00C H 0.6068 -0.4512 0.3967 0.087 Uiso 1 1 calc R . . . .
H00F H 0.6893 -0.3411 0.4171 0.087 Uiso 1 1 calc R . . . .
C00G C 0.28522(16) 0.9618(3) 0.40768(14) 0.0906(8) Uani 1 1 d . . . . .
H00G H 0.2364 0.9273 0.4215 0.136 Uiso 1 1 calc GR . . . .
H00H H 0.2706 1.0293 0.3675 0.136 Uiso 1 1 calc GR . . . .
H00I H 0.3189 1.0360 0.4408 0.136 Uiso 1 1 calc GR . . . .
C00H C 0.67209(16) -0.4486(4) 0.32567(13) 0.1076(10) Uani 1 1 d . . . . .
H00J H 0.6258 -0.4772 0.2909 0.161 Uiso 1 1 calc GR . . . .
H00K H 0.7023 -0.5578 0.3400 0.161 Uiso 1 1 calc GR . . . .
H00L H 0.7069 -0.3636 0.3101 0.161 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
C007 O001 C00F 116.36(14) . . ?
C008 N002 C005 128.15(13) . . ?
C009 N002 C005 126.66(15) . . ?
C009 N002 C008 105.19(14) . . ?
C009 N004 C006 104.39(14) . . ?
C00A C005 N002 120.51(15) . . ?
C00B C005 N002 120.52(15) . . ?
C00B C005 C00A 118.96(17) . . ?
N004 C006 C007 123.53(14) . . ?
C008 C006 N004 110.46(15) . . ?
C008 C006 C007 126.01(15) . . ?
O001 C007 C006 112.88(14) . . ?
O003 C007 O001 123.22(17) . . ?
O003 C007 C006 123.90(16) . . ?
N002 C008 H008 126.6 . . ?
C006 C008 N002 106.87(14) . . ?
C006 C008 H008 126.6 . . ?
N002 C009 H009 123.5 . . ?
N004 C009 N002 113.08(16) . . ?
N004 C009 H009 123.5 . . ?
C005 C00A H00A 120.1 . . ?
C005 C00A C00E 119.88(17) . . ?
C00E C00A H00A 120.1 . . ?
C005 C00B H00B 120.1 . . ?
C005 C00B C00D 119.78(18) . . ?
C00D C00B H00B 120.1 . . ?
C00D C00C C00G 122.0(2) . . ?
C00E C00C C00D 116.81(18) . . ?
C00E C00C C00G 121.2(2) . . ?
C00B C00D H00D 119.0 . . ?
C00C C00D C00B 122.00(18) . . ?
C00C C00D H00D 119.0 . . ?
C00A C00E H00E 118.7 . . ?
C00C C00E C00A 122.57(19) . . ?
C00C C00E H00E 118.7 . . ?
O001 C00F H00C 110.2 . . ?
O001 C00F H00F 110.2 . . ?
O001 C00F C00H 107.62(18) . . ?
H00C C00F H00F 108.5 . . ?
C00H C00F H00C 110.2 . . ?
C00H C00F H00F 110.2 . . ?
C00C C00G H00G 109.5 . . ?
C00C C00G H00H 109.5 . . ?
C00C C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C00F C00H H00J 109.5 . . ?
C00F C00H H00K 109.5 . . ?
C00F C00H H00L 109.5 . . ?
H00J C00H H00K 109.5 . . ?
H00J C00H H00L 109.5 . . ?
H00K C00H H00L 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
O001 C007 1.332(2) . ?
O001 C00F 1.453(2) . ?
N002 C005 1.436(2) . ?
N002 C008 1.367(2) . ?
N002 C009 1.356(2) . ?
O003 C007 1.197(2) . ?
N004 C006 1.363(2) . ?
N004 C009 1.312(2) . ?
C005 C00A 1.378(2) . ?
C005 C00B 1.377(2) . ?
C006 C007 1.467(2) . ?
C006 C008 1.353(2) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00E 1.380(3) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.385(3) . ?
C00C C00D 1.381(3) . ?
C00C C00E 1.365(3) . ?
C00C C00G 1.512(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00C 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00H 1.481(3) . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00H H00L 0.9600 . ?
