#------------------------------------------------------------------------------
#$Date: 2019-10-28 10:59:28 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/47/4514787.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_4514787
loop_
_publ_author_name
'Wu, Wenli'
'Cui, Enxin'
'Zhang, Yun'
'Zhang, Chen'
'Zhu, Feng'
'Tung, Chen-Ho'
'Wang, Yifeng'
_publ_section_title
;
 Involving Single-Atom Silver(0) in Selective Dehalogenation by AgF under
 Visible-Light Irradiation
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6335
_journal_paper_doi               10.1021/acscatal.9b01929
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C8 H6 N'
_chemical_formula_sum            'C8 H6 N'
_chemical_formula_weight         116.14
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.593(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8048(3)
_cell_length_b                   5.9454(3)
_cell_length_c                   13.2408(5)
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    172.98(10)
_cell_measurement_theta_max      75.4910
_cell_measurement_theta_min      6.4370
_cell_volume                     613.78(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      172.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -62.00 -37.00   1.00    0.10    --  -86.25 142.00-137.00   25
  2  ω    -96.00 -23.00   1.00    0.10    --  -48.45 142.00-137.00   73
  3  ω     37.00 123.00   1.00    0.10    --  107.75 -57.00 -60.00   86
  4  ω    110.00 135.00   1.00    0.10    --  107.75 128.00  51.00   25
  5  ω   -118.00 -26.00   1.00    0.10    --  -48.45 -77.00  90.00   92
  6  ω   -105.00 -70.00   1.00    0.10    --  -86.25-128.00 -23.00   35
  7  ω   -120.00 -72.00   1.00    0.10    --  -48.45-128.00 -23.00   48
  8  ω    -86.00 -61.00   1.00    0.10    --  -48.45-142.00 165.00   25
  9  ω   -158.00 -83.00   1.00    0.10    --  -86.25 -99.00-120.00   75
 10  ω     56.00  81.00   1.00    0.10    --   48.45-142.00 165.00   25
 11  ω     42.00 129.00   1.00    0.10    --  107.75-142.00 165.00   87
 12  ω     58.00 122.00   1.00    0.10    --  107.75-128.00 -23.00   64
 13  ω     96.00 134.00   1.00    0.10    --  107.75  37.00 -30.00   38
 14  ω    153.00 178.00   1.00    0.10    --  107.75  37.00 -30.00   25
 15  ω     86.00 174.00   1.00    0.10    --  107.75  77.00 120.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362116000
_diffrn_orient_matrix_UB_12      -0.2510083000
_diffrn_orient_matrix_UB_13      -0.0181512000
_diffrn_orient_matrix_UB_21      -0.1650859000
_diffrn_orient_matrix_UB_22      -0.0629898000
_diffrn_orient_matrix_UB_23      0.0530070000
_diffrn_orient_matrix_UB_31      -0.1023929000
_diffrn_orient_matrix_UB_32      0.0124601000
_diffrn_orient_matrix_UB_33      -0.1021084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3467
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.353
_diffrn_reflns_theta_min         6.458
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
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    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0523
_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)+(0.0823P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                987
_reflns_number_total             1219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b01929_si_004.cif
_cod_data_source_block           exp_283
_cod_database_code               4514787
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C N H '
_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 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6)
;
_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 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.562
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
N1 N 0.71004(19) 0.5460(3) 0.17563(11) 0.0443(5) Uani 1 1 d .
C7 C 0.6111(2) 0.5304(3) 0.23691(12) 0.0337(4) Uani 1 1 d .
C3 C 0.3257(2) 0.6657(3) 0.44606(12) 0.0320(4) Uani 1 1 d .
H3 H 0.3056 0.7839 0.4900 0.038 Uiso 1 1 calc R
C4 C 0.2267(2) 0.4703(3) 0.45016(12) 0.0311(4) Uani 1 1 d .
C5 C 0.2591(2) 0.2959(3) 0.38368(12) 0.0340(4) Uani 1 1 d .
H5 H 0.1943 0.1649 0.3860 0.041 Uiso 1 1 calc R
C2 C 0.4533(2) 0.6853(3) 0.37733(12) 0.0322(4) Uani 1 1 d .
H2 H 0.5191 0.8155 0.3755 0.039 Uiso 1 1 calc R
C1 C 0.48252(19) 0.5095(3) 0.31100(11) 0.0300(4) Uani 1 1 d .
C8 C 0.0841(2) 0.4520(3) 0.52246(12) 0.0355(5) Uani 1 1 d .
H8A H 0.1163 0.5324 0.5842 0.043 Uiso 1 1 calc R
H8B H 0.0675 0.2952 0.5397 0.043 Uiso 1 1 calc R
C6 C 0.3853(2) 0.3129(3) 0.31427(12) 0.0331(4) Uani 1 1 d .
H6 H 0.4053 0.1948 0.2703 0.040 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
N1 C7 C1 178.01(17) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C2 C3 C4 120.73(15) . .
C3 C4 C8 120.72(15) . .
C5 C4 C3 118.60(14) . .
C5 C4 C8 120.64(15) . .
C4 C5 H5 119.3 . .
C6 C5 C4 121.46(15) . .
C6 C5 H5 119.3 . .
C3 C2 H2 120.2 . .
C3 C2 C1 119.69(15) . .
C1 C2 H2 120.2 . .
C2 C1 C7 120.29(14) . .
C2 C1 C6 120.34(14) . .
C6 C1 C7 119.36(14) . .
C4 C8 C8 111.89(15) . 3_566
C4 C8 H8A 109.2 . .
C4 C8 H8B 109.2 . .
C8 C8 H8A 109.2 3_566 .
C8 C8 H8B 109.2 3_566 .
H8A C8 H8B 107.9 . .
C5 C6 C1 119.18(14) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.149(2) .
C7 C1 1.440(2) .
C3 H3 0.9300 .
C3 C4 1.398(2) .
C3 C2 1.384(2) .
C4 C5 1.391(2) .
C4 C8 1.505(2) .
C5 H5 0.9300 .
C5 C6 1.381(2) .
C2 H2 0.9300 .
C2 C1 1.391(2) .
C1 C6 1.395(2) .
C8 C8 1.527(3) 3_566
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C6 H6 0.9300 .
