#------------------------------------------------------------------------------
#$Date: 2021-10-06 16:46:44 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269614 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/88/7128835.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_7128835
loop_
_publ_author_name
'Chen, Fangyuan'
'Tang, Junyuan'
'Wei, Yinhui'
'Tian, Jingyuan'
'Gao, Hui'
'Yi, Wei'
'Zhou, Zhi'
_publ_section_title
;
 Rh(III)-Catalyzed and synergistic dual directing group-enabled
 redox-neutral [3+3] annulation of N-phenoxyacetamides with
 α-allenols.
;
_journal_issue                   73
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9284
_journal_page_last               9287
_journal_paper_doi               10.1039/d1cc03206b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_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             2021-05-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-05-20 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                77.537(14)
_cell_angle_beta                 72.055(16)
_cell_angle_gamma                75.300(16)
_cell_formula_units_Z            2
_cell_length_a                   8.3313(17)
_cell_length_b                   8.8068(15)
_cell_length_c                   10.2625(15)
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1770
_cell_measurement_theta_min      3.1650
_cell_volume                     685.1(2)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  21.00   1.00    2.00    --  -11.27 -77.00 120.00   98
  2  ω    -57.00  36.00   1.00    2.00    --   11.90 -57.00-120.00   93
  3  ω    -16.00  83.00   1.00    2.00    --   11.90  57.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205759000
_diffrn_orient_matrix_UB_12      -0.0493727000
_diffrn_orient_matrix_UB_13      -0.0514824000
_diffrn_orient_matrix_UB_21      -0.0880242000
_diffrn_orient_matrix_UB_22      0.0160740000
_diffrn_orient_matrix_UB_23      0.0005210000
_diffrn_orient_matrix_UB_31      0.0132681000
_diffrn_orient_matrix_UB_32      0.0663004000
_diffrn_orient_matrix_UB_33      -0.0524220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4266
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.110
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44050
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0832
_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)+(0.1421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2123
_refine_ls_wR_factor_ref         0.2471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1561
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03206b2.cif
_cod_data_source_block           127-3
_cod_depositor_comments          'Adding full bibliography for 7128835.cif.'
_cod_database_code               7128835
_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 99.32
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C2(H2), C15(H15), C7(H7), C3(H3), C6(H6), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 4.499
_oxdiff_exptl_absorpt_empirical_full_min 0.436
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
O2 O 0.6230(2) 0.1089(2) 0.84322(18) 0.0273(6) Uani 1 1 d . . . . .
O1 O 0.3356(2) 0.1832(2) 0.96336(19) 0.0301(6) Uani 1 1 d . . . . .
H1 H 0.323697 0.099877 1.015851 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6916(4) 0.2317(3) 0.8531(3) 0.0245(7) Uani 1 1 d . . . . .
C12 C 0.6170(4) 0.3921(3) 0.8249(3) 0.0256(7) Uani 1 1 d . . . . .
C10 C 0.4462(4) 0.1496(3) 0.8339(3) 0.0273(7) Uani 1 1 d . . . . .
C8 C 0.4659(4) 0.4357(3) 0.7681(3) 0.0260(7) Uani 1 1 d . . . . .
C16 C 0.8456(4) 0.1863(3) 0.8919(3) 0.0290(7) Uani 1 1 d . . . . .
H16 H 0.894250 0.079071 0.909313 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7007(4) 0.5024(3) 0.8418(3) 0.0303(7) Uani 1 1 d . . . . .
H13 H 0.652908 0.609958 0.825556 0.036 Uiso 1 1 calc R U . . .
C1 C 0.2379(4) 0.6469(3) 0.6817(3) 0.0277(7) Uani 1 1 d . . . . .
C2 C 0.2306(4) 0.5894(3) 0.5677(3) 0.0300(8) Uani 1 1 d . . . . .
H2 H 0.317463 0.507244 0.532327 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9255(4) 0.2980(3) 0.9044(3) 0.0323(8) Uani 1 1 d . . . . .
H15 H 1.029372 0.267119 0.928130 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3769(4) 0.5856(3) 0.7499(3) 0.0281(7) Uani 1 1 d . . . . .
H7 H 0.407564 0.659628 0.785141 0.034 Uiso 1 1 calc R U . . .
C4 C -0.0358(4) 0.7728(3) 0.5559(3) 0.0318(8) Uani 1 1 d . . . . .
C9 C 0.4224(4) 0.2982(3) 0.7297(3) 0.0290(7) Uani 1 1 d . . . . .
H9A H 0.495780 0.277691 0.638882 0.035 Uiso 1 1 calc R U . . .
H9B H 0.303882 0.325800 0.724821 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0968(4) 0.6519(3) 0.5061(3) 0.0301(7) Uani 1 1 d . . . . .
H3 H 0.096263 0.611623 0.429681 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1073(4) 0.7739(3) 0.7274(3) 0.0297(7) Uani 1 1 d . . . . .
H6 H 0.110743 0.818815 0.800418 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4186(4) 0.0062(3) 0.7930(3) 0.0322(8) Uani 1 1 d . . . . .
H17A H 0.492902 -0.009323 0.702493 0.048 Uiso 1 1 calc R U . . .
H17B H 0.300756 0.022072 0.791583 0.048 Uiso 1 1 calc R U . . .
H17C H 0.444485 -0.085692 0.858658 0.048 Uiso 1 1 calc R U . . .
C5 C -0.0274(4) 0.8345(3) 0.6664(3) 0.0336(8) Uani 1 1 d . . . . .
H5 H -0.113613 0.918029 0.700124 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8510(4) 0.4576(4) 0.8815(3) 0.0337(8) Uani 1 1 d . . . . .
H14 H 0.902695 0.534060 0.892963 0.040 Uiso 1 1 calc R U . . .
C18 C -0.1848(4) 0.8348(4) 0.4915(3) 0.0416(9) Uani 1 1 d . . . . .
H18A H -0.145814 0.823714 0.395045 0.062 Uiso 1 1 calc R U . . .
H18B H -0.229395 0.944843 0.500792 0.062 Uiso 1 1 calc R U . . .
H18C H -0.273722 0.775352 0.537580 0.062 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 0.0033 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'
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
C11 O2 C10 116.43(19) . . ?
C10 O1 H1 109.5 . . ?
O2 C11 C12 123.7(3) . . ?
O2 C11 C16 115.5(2) . . ?
C16 C11 C12 120.8(3) . . ?
C11 C12 C8 119.1(3) . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 C8 123.8(2) . . ?
O2 C10 C9 109.6(2) . . ?
O2 C10 C17 105.1(2) . . ?
O1 C10 O2 108.9(2) . . ?
O1 C10 C9 107.6(2) . . ?
O1 C10 C17 112.4(2) . . ?
C17 C10 C9 113.2(2) . . ?
C12 C8 C9 114.1(2) . . ?
C7 C8 C12 122.9(3) . . ?
C7 C8 C9 122.9(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13 118.8 . . ?
C2 C1 C7 123.5(2) . . ?
C2 C1 C6 116.8(3) . . ?
C6 C1 C7 119.6(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C8 C7 C1 128.3(3) . . ?
C8 C7 H7 115.9 . . ?
C1 C7 H7 115.9 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C18 120.7(3) . . ?
C5 C4 C18 121.5(3) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 C10 111.6(2) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 C11 1.380(3) . ?
O2 C10 1.453(3) . ?
O1 H1 0.8200 . ?
O1 C10 1.406(3) . ?
C11 C12 1.398(4) . ?
C11 C16 1.396(4) . ?
C12 C8 1.477(4) . ?
C12 C13 1.397(4) . ?
C10 C9 1.513(4) . ?
C10 C17 1.504(4) . ?
C8 C7 1.345(4) . ?
C8 C9 1.506(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C1 C2 1.394(4) . ?
C1 C7 1.463(4) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C7 H7 0.9300 . ?
C4 C3 1.380(4) . ?
C4 C5 1.386(4) . ?
C4 C18 1.510(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.387(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O2 C11 C12 C8 -6.2(4) . . . . ?
O2 C11 C12 C13 179.0(2) . . . . ?
O2 C11 C16 C15 179.7(2) . . . . ?
O2 C10 C9 C8 -58.2(3) . . . . ?
O1 C10 C9 C8 60.1(3) . . . . ?
C11 O2 C10 O1 -71.5(3) . . . . ?
C11 O2 C10 C9 45.9(3) . . . . ?
C11 O2 C10 C17 167.8(2) . . . . ?
C11 C12 C8 C7 173.8(3) . . . . ?
C11 C12 C8 C9 -7.5(4) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C11 C16 C15 C14 1.5(4) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C8 C7 C1 172.8(3) . . . . ?
C12 C8 C9 C10 39.2(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C10 O2 C11 C12 -14.4(4) . . . . ?
C10 O2 C11 C16 166.7(2) . . . . ?
C8 C12 C13 C14 -173.2(2) . . . . ?
C16 C11 C12 C8 172.7(2) . . . . ?
C16 C11 C12 C13 -2.0(4) . . . . ?
C16 C15 C14 C13 -2.2(4) . . . . ?
C13 C12 C8 C7 -11.9(4) . . . . ?
C13 C12 C8 C9 166.9(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C2 C1 C7 C8 -34.4(4) . . . . ?
C2 C1 C6 C5 3.0(4) . . . . ?
C7 C8 C9 C10 -142.1(3) . . . . ?
C7 C1 C2 C3 -179.7(2) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C9 C8 C7 C1 -5.9(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C6 C1 C2 C3 -2.1(4) . . . . ?
C6 C1 C7 C8 148.2(3) . . . . ?
C17 C10 C9 C8 -175.1(2) . . . . ?
C5 C4 C3 C2 2.6(4) . . . . ?
C18 C4 C3 C2 -177.3(3) . . . . ?
C18 C4 C5 C6 178.2(3) . . . . ?
