#------------------------------------------------------------------------------
#$Date: 2022-02-09 00:52:30 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129681.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_7129681
loop_
_publ_author_name
'Liu, Ce'
'Shi, Wei-Yu'
'Ding, Ya-Nan'
'Zheng, Nian'
'Liang, Yong-Min'
_publ_section_title
;
 Palladium-Catalyzed Rearrangement Reaction to Access 1-Phenanthrol
 Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00392A
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 O'
_chemical_formula_sum            'C16 H14 O'
_chemical_formula_weight         222.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-22 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.149(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9314(10)
_cell_length_b                   5.2194(3)
_cell_length_c                   13.7603(8)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8240
_cell_measurement_theta_min      6.6630
_cell_volume                     1173.76(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  25.00   1.00    1.00    --    0.00  57.00   0.00   27
  2  ω     29.00  63.00   1.00    1.00    --    0.00  57.00   0.00   34
  3  ω     31.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   38
  4  ω     35.00  63.00   1.00    1.00    --   54.00  77.00-120.00   28
  5  ω     36.00 118.00   1.00    1.00    --   54.00  57.00-120.00   82
  6  ω     79.00 104.00   1.00    2.00    --  108.00  77.00 -90.00   25
  7  ω    119.00 177.00   1.00    2.00    --  108.00  77.00-120.00   58
  8  ω    124.00 150.00   1.00    2.00    --  108.00 101.00 -13.00   26
  9  ω    150.00 177.00   1.00    2.00    --  108.00 111.00   0.00   27
 10  ω    121.00 174.00   1.00    2.00    --  108.00  77.00 -90.00   53
 11  ω    120.00 175.00   1.00    2.00    --  108.00  77.00-180.00   55
 12  ω    117.00 176.00   1.00    2.00    --  108.00  77.00-150.00   59
 13  ω    117.00 178.00   1.00    2.00    --  108.00  77.00 -30.00   61
 14  ω    122.00 174.00   1.00    2.00    --  108.00 111.00  30.00   52
 15  ω    100.00 147.00   1.00    2.00    --  108.00 111.00   0.00   47
 16  ω     91.00 119.00   1.00    2.00    --  108.00  50.00 -60.00   28
 17  ω     86.00 172.00   1.00    2.00    --  108.00  63.00 -60.00   86
 18  ω     94.00 121.00   1.00    2.00    --  108.00  50.00-120.00   27
 19  ω     87.00 115.00   1.00    2.00    --  108.00  63.00-150.00   28
 20  ω     88.00 116.00   1.00    2.00    --  108.00  50.00-150.00   28
 21  ω     82.00 109.00   1.00    2.00    --  108.00  38.00 -90.00   27
 22  ω     88.00 114.00   1.00    2.00    --  108.00  63.00 -90.00   26
 23  ω     83.00 109.00   1.00    2.00    --  108.00  38.00-120.00   26
 24  ω     83.00 108.00   1.00    2.00    --  108.00  38.00-150.00   25
 25  ω     87.00 112.00   1.00    2.00    --  108.00  63.00-180.00   25
 26  ω     80.00 107.00   1.00    2.00    --  108.00  77.00-150.00   27
 27  ω     79.00 104.00   1.00    2.00    --  108.00  77.00-180.00   25
 28  ω     78.00 104.00   1.00    2.00    --  108.00  77.00-120.00   26
 29  ω     86.00 117.00   1.00    2.00    --  108.00  50.00 -90.00   31
 30  ω     82.00 108.00   1.00    2.00    --  108.00  38.00 -60.00   26
 31  ω     83.00 110.00   1.00    2.00    --  108.00  38.00 -30.00   27
 32  ω     36.00  72.00   1.00    1.00    --   54.00 -57.00-120.00   36
 33  ω     27.00 104.00   1.00    1.00    --   54.00-125.00-120.00   77
 34  ω     49.00 138.00   1.00    2.00    --  108.00 -77.00  60.00   89
 35  ω     86.00 172.00   1.00    2.00    --  108.00  77.00 150.00   86
 36  ω     26.00  73.00   1.00    1.00    --   54.00  77.00 -60.00   47
 37  ω     15.00 125.00   1.00    1.00    --   54.00  19.00-180.00  110
 38  ω     -9.00  72.00   1.00    1.00    --   54.00 -57.00   0.00   81
 39  ω    -14.00  28.00   1.00    1.00    --    0.00  57.00 -90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372058000
_diffrn_orient_matrix_UB_12      -0.0595967000
_diffrn_orient_matrix_UB_13      0.0883951000
_diffrn_orient_matrix_UB_21      0.0819465000
_diffrn_orient_matrix_UB_22      -0.1175576000
_diffrn_orient_matrix_UB_23      0.0591945000
_diffrn_orient_matrix_UB_31      0.0280163000
_diffrn_orient_matrix_UB_32      0.2640572000
_diffrn_orient_matrix_UB_33      0.0462774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         6.506
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0030(7)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0398
_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)+(0.0756P)²+0.0610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1703
_reflns_number_total             2086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00392a2.cif
_cod_data_source_block           liuc_0323
_cod_database_code               7129681
_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.
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2020-03-23
_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.664
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
O1 O 0.03108(6) 0.24647(19) 0.29447(8) 0.0694(3) Uani 1 1 d . . . . .
H1 H 0.010614 0.116620 0.264769 0.104 Uiso 1 1 calc R U . . .
C1 C 0.16119(7) 0.4192(2) 0.37624(8) 0.0471(3) Uani 1 1 d . . . . .
C2 C 0.11474(8) 0.2413(2) 0.30736(9) 0.0531(3) Uani 1 1 d . . . . .
C3 C 0.15038(9) 0.0754(3) 0.25470(10) 0.0610(4) Uani 1 1 d . . . . .
H3 H 0.118400 -0.038874 0.209090 0.073 Uiso 1 1 calc R U . . .
C4 C 0.23490(10) 0.0788(3) 0.26989(10) 0.0648(4) Uani 1 1 d . . . . .
H4 H 0.259499 -0.036259 0.235239 0.078 Uiso 1 1 calc R U . . .
C5 C 0.28208(9) 0.2496(3) 0.33527(11) 0.0603(4) Uani 1 1 d . . . . .
H5 H 0.338450 0.250133 0.344116 0.072 Uiso 1 1 calc R U . . .
C6 C 0.24684(8) 0.4248(2) 0.38944(9) 0.0492(3) Uani 1 1 d . . . . .
C7 C 0.29428(8) 0.6094(2) 0.45985(9) 0.0497(3) Uani 1 1 d . . . . .
C8 C 0.25517(8) 0.7727(2) 0.51498(9) 0.0490(3) Uani 1 1 d . . . . .
C9 C 0.16787(8) 0.7576(2) 0.50063(9) 0.0480(3) Uani 1 1 d . . . . .
C10 C 0.12425(7) 0.5871(2) 0.43360(9) 0.0495(3) Uani 1 1 d . . . . .
H10 H 0.067912 0.579022 0.424506 0.059 Uiso 1 1 calc R U . . .
C11 C 0.37956(8) 0.6343(3) 0.47542(11) 0.0640(4) Uani 1 1 d . . . . .
H11 H 0.406338 0.530410 0.439262 0.077 Uiso 1 1 calc R U . . .
C12 C 0.42389(9) 0.8076(3) 0.54248(12) 0.0695(4) Uani 1 1 d . . . . .
H12 H 0.480174 0.817921 0.551414 0.083 Uiso 1 1 calc R U . . .
C13 C 0.38632(9) 0.9694(3) 0.59777(11) 0.0624(4) Uani 1 1 d . . . . .
C14 C 0.30308(9) 0.9501(3) 0.58296(10) 0.0570(3) Uani 1 1 d . . . . .
H14 H 0.277357 1.057842 0.619020 0.068 Uiso 1 1 calc R U . . .
C15 C 0.12554(9) 0.9319(3) 0.55827(11) 0.0610(4) Uani 1 1 d . . . . .
H15A H 0.151586 0.918337 0.628961 0.091 Uiso 1 1 calc R U . . .
H15B H 0.069127 0.882820 0.545821 0.091 Uiso 1 1 calc R U . . .
H15C H 0.128902 1.105582 0.536759 0.091 Uiso 1 1 calc R U . . .
C16 C 0.43606(11) 1.1618(4) 0.67111(14) 0.0813(5) Uani 1 1 d . . . . .
H16A H 0.406149 1.319559 0.666569 0.122 Uiso 1 1 calc R U . . .
H16B H 0.487072 1.192466 0.654933 0.122 Uiso 1 1 calc R U . . .
H16C H 0.446500 1.095460 0.738342 0.122 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 0.0181 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'
O O 0.0492 0.0322 '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
C2 O1 H1 109.5 . . ?
C2 C1 C6 118.23(11) . . ?
C2 C1 C10 121.83(12) . . ?
C6 C1 C10 119.92(11) . . ?
O1 C2 C1 116.52(11) . . ?
C3 C2 O1 121.64(12) . . ?
C3 C2 C1 121.83(13) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.45(13) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.57(13) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.13(13) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 118.02(11) . . ?
C5 C6 C1 118.76(12) . . ?
C5 C6 C7 123.21(12) . . ?
C8 C7 C6 120.19(11) . . ?
C11 C7 C6 121.96(12) . . ?
C11 C7 C8 117.86(12) . . ?
C7 C8 C9 120.04(11) . . ?
C14 C8 C7 118.80(12) . . ?
C14 C8 C9 121.16(12) . . ?
C8 C9 C15 120.48(11) . . ?
C10 C9 C8 119.12(11) . . ?
C10 C9 C15 120.39(12) . . ?
C1 C10 H10 118.7 . . ?
C9 C10 C1 122.69(12) . . ?
C9 C10 H10 118.7 . . ?
C7 C11 H11 119.2 . . ?
C12 C11 C7 121.56(14) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.32(14) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C16 120.74(14) . . ?
C14 C13 C12 118.07(13) . . ?
C14 C13 C16 121.19(15) . . ?
C8 C14 H14 118.8 . . ?
C13 C14 C8 122.39(13) . . ?
C13 C14 H14 118.8 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 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 H1 0.8200 . ?
O1 C2 1.3811(16) . ?
C1 C2 1.4106(18) . ?
C1 C6 1.4139(17) . ?
C1 C10 1.4286(17) . ?
C2 C3 1.3666(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4072(18) . ?
C6 C7 1.4509(18) . ?
C7 C8 1.4153(18) . ?
C7 C11 1.4092(18) . ?
C8 C9 1.4412(17) . ?
C8 C14 1.4123(18) . ?
C9 C10 1.3535(17) . ?
C9 C15 1.5057(17) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.368(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(2) . ?
C13 C14 1.374(2) . ?
C13 C16 1.514(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 C2 C3 C4 179.57(12) . . . . ?
C1 C2 C3 C4 0.77(19) . . . . ?
C1 C6 C7 C8 1.65(16) . . . . ?
C1 C6 C7 C11 -177.92(11) . . . . ?
C2 C1 C6 C5 -1.40(16) . . . . ?
C2 C1 C6 C7 179.58(10) . . . . ?
C2 C1 C10 C9 179.44(11) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.88(19) . . . . ?
C4 C5 C6 C7 179.85(12) . . . . ?
C5 C6 C7 C8 -177.33(11) . . . . ?
C5 C6 C7 C11 3.10(19) . . . . ?
C6 C1 C2 O1 -178.26(10) . . . . ?
C6 C1 C2 C3 0.60(18) . . . . ?
C6 C1 C10 C9 0.85(17) . . . . ?
C6 C7 C8 C9 -0.56(16) . . . . ?
C6 C7 C8 C14 179.96(10) . . . . ?
C6 C7 C11 C12 -179.54(12) . . . . ?
C7 C8 C9 C10 -0.42(16) . . . . ?
C7 C8 C9 C15 -179.51(11) . . . . ?
C7 C8 C14 C13 -0.21(18) . . . . ?
C7 C11 C12 C13 -0.6(2) . . . . ?
C8 C7 C11 C12 0.9(2) . . . . ?
C8 C9 C10 C1 0.29(17) . . . . ?
C9 C8 C14 C13 -179.69(11) . . . . ?
C10 C1 C2 O1 3.13(17) . . . . ?
C10 C1 C2 C3 -178.01(11) . . . . ?
C10 C1 C6 C5 177.24(11) . . . . ?
C10 C1 C6 C7 -1.78(16) . . . . ?
C11 C7 C8 C9 179.03(11) . . . . ?
C11 C7 C8 C14 -0.45(17) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C11 C12 C13 C16 -179.51(14) . . . . ?
C12 C13 C14 C8 0.5(2) . . . . ?
C14 C8 C9 C10 179.05(11) . . . . ?
C14 C8 C9 C15 -0.04(17) . . . . ?
C15 C9 C10 C1 179.37(11) . . . . ?
C16 C13 C14 C8 179.93(12) . . . . ?
