#------------------------------------------------------------------------------
#$Date: 2021-06-08 04:16:31 +0300 (Tue, 08 Jun 2021) $
#$Revision: 266239 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/32/1563206.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_1563206
loop_
_publ_author_name
'chen, Herong'
'Zhou, Zhijun'
'Kong, Wangqing'
_publ_section_title
;
 Allylic Alcohol Synthesis by Ni-Catalyzed Direct and Selective Coupling
 of Alkynes and Methanol
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02625A
_journal_year                    2021
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_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     dual
_audit_creation_date             2019-05-23
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2021-01-23 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.989(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8774(4)
_cell_length_b                   11.4152(4)
_cell_length_c                   13.2381(5)
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.40
_cell_measurement_theta_min      5.01
_cell_volume                     1334.19(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7918
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        64.990
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_min         5.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0102(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0329
_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)+(0.0424P)²+0.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1919
_reflns_number_total             2166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02625a2.cif
_cod_data_source_block           cu_190522c_0m
_cod_database_code               1563206
_shelx_shelxl_version_number     2014/7
_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   0.933
_shelx_estimated_absorpt_t_min   0.920
_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), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7) 
2.c Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.37792(16) 0.68748(12) 0.07660(11) 0.0421(3) Uani 1 1 d . . . . .
C2 C 0.26852(16) 0.76102(12) 0.11009(11) 0.0452(4) Uani 1 1 d . . . . .
H2A H 0.2243 0.7418 0.1686 0.054 Uiso 1 1 calc R . . . .
C3 C 0.22452(18) 0.86204(12) 0.05788(12) 0.0504(4) Uani 1 1 d . . . . .
H3 H 0.1520 0.9105 0.0820 0.060 Uiso 1 1 calc R . . . .
C4 C 0.28692(19) 0.89172(14) -0.02956(13) 0.0561(4) Uani 1 1 d . . . . .
H4 H 0.2564 0.9596 -0.0648 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3955(2) 0.81962(15) -0.06443(13) 0.0607(4) Uani 1 1 d . . . . .
H5 H 0.4378 0.8387 -0.1237 0.073 Uiso 1 1 calc R . . . .
C6 C 0.44108(17) 0.71941(14) -0.01153(12) 0.0533(4) Uani 1 1 d . . . . .
H6 H 0.5154 0.6723 -0.0351 0.064 Uiso 1 1 calc R . . . .
C7 C 0.43165(16) 0.58233(12) 0.13435(11) 0.0453(3) Uani 1 1 d . . . . .
H7 H 0.5356 0.5693 0.1410 0.054 Uiso 1 1 calc R . . . .
C8 C 0.34814(15) 0.50420(11) 0.17786(10) 0.0392(3) Uani 1 1 d . . . . .
C9 C 0.17848(14) 0.50035(11) 0.16628(9) 0.0368(3) Uani 1 1 d . . . . .
H9A H 0.1407 0.5463 0.1074 0.044 Uiso 1 1 calc R . . . .
H9B H 0.1415 0.5359 0.2255 0.044 Uiso 1 1 calc R . . . .
C10 C 0.11627(15) 0.37574(11) 0.15394(9) 0.0350(3) Uani 1 1 d . . . . .
C11 C 0.19727(17) 0.28930(12) 0.23079(10) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.42070(18) 0.41072(12) 0.24643(11) 0.0496(4) Uani 1 1 d . . . . .
H12A H 0.5282 0.4078 0.2389 0.060 Uiso 1 1 calc R . . . .
H12B H 0.4095 0.4311 0.3164 0.060 Uiso 1 1 calc R . . . .
C13 C 0.15723(18) 0.16841(12) 0.18763(11) 0.0488(4) Uani 1 1 d . . . . .
H13A H 0.0570 0.1447 0.2026 0.059 Uiso 1 1 calc R . . . .
H13B H 0.2304 0.1103 0.2147 0.059 Uiso 1 1 calc R . . . .
C14 C 0.16255(18) 0.18475(12) 0.07366(11) 0.0453(4) Uani 1 1 d . . . . .
H14A H 0.2580 0.1567 0.0532 0.054 Uiso 1 1 calc R . . . .
H14B H 0.0804 0.1425 0.0356 0.054 Uiso 1 1 calc R . . . .
C15 C 0.14626(15) 0.31539(11) 0.05562(9) 0.0357(3) Uani 1 1 d . . . . .
C16 C -0.05618(16) 0.37646(13) 0.15702(12) 0.0495(4) Uani 1 1 d . . . . .
H16A H -0.1012 0.4328 0.1092 0.074 Uiso 1 1 calc GR . . . .
H16B H -0.0790 0.3969 0.2241 0.074 Uiso 1 1 calc GR . . . .
H16C H -0.0961 0.3001 0.1397 0.074 Uiso 1 1 calc GR . . . .
O1 O 0.35612(11) 0.29713(8) 0.22509(7) 0.0449(3) Uani 1 1 d . . . . .
O2 O 0.15853(15) 0.31307(10) 0.32814(7) 0.0628(3) Uani 1 1 d . . . . .
H2 H 0.1727 0.2544 0.3637 0.094 Uiso 1 1 calc GR . . . .
O3 O 0.15508(12) 0.36371(9) -0.02488(7) 0.0500(3) Uani 1 1 d . . . . .
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 C1 C6 117.65(13) . . ?
C2 C1 C7 121.65(13) . . ?
C6 C1 C7 120.64(13) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.02(14) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.61(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.33(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.13(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.26(15) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 116.4 . . ?
C8 C7 C1 127.29(13) . . ?
C8 C7 H7 116.4 . . ?
C7 C8 C9 125.14(12) . . ?
C7 C8 C12 121.02(13) . . ?
C9 C8 C12 113.83(12) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C8 C9 C10 112.73(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 C11 112.77(11) . . ?
C9 C10 C16 110.01(10) . . ?
C15 C10 C9 114.80(10) . . ?
C15 C10 C11 99.42(10) . . ?
C15 C10 C16 106.81(11) . . ?
C16 C10 C11 112.57(11) . . ?
C13 C11 C10 104.97(11) . . ?
O1 C11 C10 108.76(10) . . ?
O1 C11 C13 103.36(11) . . ?
O2 C11 C10 110.03(11) . . ?
O2 C11 C13 116.94(12) . . ?
O2 C11 O1 112.22(11) . . ?
C8 C12 H12A 109.1 . . ?
C8 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O1 C12 C8 112.70(11) . . ?
O1 C12 H12A 109.1 . . ?
O1 C12 H12B 109.1 . . ?
C11 C13 H13A 111.1 . . ?
C11 C13 H13B 111.1 . . ?
C11 C13 C14 103.32(10) . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C15 C14 C13 105.31(11) . . ?
C15 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
C14 C15 C10 109.48(10) . . ?
O3 C15 C10 125.50(11) . . ?
O3 C15 C14 125.02(12) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O1 C12 115.12(11) . . ?
C11 O2 H2 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
C1 C2 1.391(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.475(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3288(19) . ?
C8 C9 1.4986(19) . ?
C8 C12 1.5019(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5284(17) . ?
C10 C11 1.5405(18) . ?
C10 C15 1.5206(17) . ?
C10 C16 1.5357(19) . ?
C11 C13 1.522(2) . ?
C11 O1 1.4228(17) . ?
C11 O2 1.3947(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 O1 1.4339(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.526(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5148(18) . ?
C15 O3 1.2097(15) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O2 H2 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 2.02 2.8055(14) 161.1 4_566
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
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C7 C8 C9 7.6(2) . . . . ?
C1 C7 C8 C12 -171.39(13) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C7 C8 43.6(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C7 C8 -139.49(16) . . . . ?
C7 C1 C2 C3 176.90(12) . . . . ?
C7 C1 C6 C5 -177.83(14) . . . . ?
C7 C8 C9 C10 138.81(13) . . . . ?
C7 C8 C12 O1 -134.31(14) . . . . ?
C8 C9 C10 C11 45.77(14) . . . . ?
C8 C9 C10 C15 -67.16(14) . . . . ?
C8 C9 C10 C16 172.35(11) . . . . ?
C8 C12 O1 C11 -57.23(16) . . . . ?
C9 C8 C12 O1 46.62(17) . . . . ?
C9 C10 C11 C13 -163.01(11) . . . . ?
C9 C10 C11 O1 -52.93(14) . . . . ?
C9 C10 C11 O2 70.36(15) . . . . ?
C9 C10 C15 C14 148.79(12) . . . . ?
C9 C10 C15 O3 -31.56(18) . . . . ?
C10 C11 C13 C14 39.02(14) . . . . ?
C10 C11 O1 C12 59.42(13) . . . . ?
C11 C10 C15 C14 28.20(14) . . . . ?
C11 C10 C15 O3 -152.15(13) . . . . ?
C11 C13 C14 C15 -20.39(15) . . . . ?
C12 C8 C9 C10 -42.16(15) . . . . ?
C13 C11 O1 C12 170.59(10) . . . . ?
C13 C14 C15 C10 -5.40(16) . . . . ?
C13 C14 C15 O3 174.95(13) . . . . ?
C15 C10 C11 C13 -40.95(13) . . . . ?
C15 C10 C11 O1 69.14(12) . . . . ?
C15 C10 C11 O2 -167.57(11) . . . . ?
C16 C10 C11 C13 71.79(14) . . . . ?
C16 C10 C11 O1 -178.13(10) . . . . ?
C16 C10 C11 O2 -54.84(15) . . . . ?
C16 C10 C15 C14 -88.97(13) . . . . ?
C16 C10 C15 O3 90.69(15) . . . . ?
O1 C11 C13 C14 -74.91(12) . . . . ?
O2 C11 C13 C14 161.27(12) . . . . ?
O2 C11 O1 C12 -62.55(14) . . . . ?
