#------------------------------------------------------------------------------
#$Date: 2020-09-04 00:22:50 +0300 (Fri, 04 Sep 2020) $
#$Revision: 255828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/79/4517995.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_4517995
loop_
_publ_author_name
'Lv, Weiwei'
'Liu, Shihan'
'Chen, Yanhui'
'Wen, Si'
'Lan, Yu'
'Cheng, Guolin'
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Trans-Selective Carbofunctionalization
 of Internal Alkynes to Highly Functionalized Alkenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10516
_journal_paper_doi               10.1021/acscatal.0c02522
_journal_year                    2020
_chemical_formula_moiety         'C30 H28 O2'
_chemical_formula_sum            'C30 H28 O2'
_chemical_formula_weight         420.52
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.201(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0772(16)
_cell_length_b                   15.556(2)
_cell_length_c                   14.641(2)
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0820
_cell_measurement_theta_min      4.2850
_cell_volume                     2367.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9525
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.86
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.9092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                2967
_reflns_number_total             4643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs0c02522_si_002.cif
_cod_data_source_block           exp_5984
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4517995
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 1.07977(16) 0.43447(12) 0.67288(14) 0.0647(5) Uani 1 1 d . . .
O002 O 0.06101(17) 0.78001(12) 0.57786(14) 0.0651(5) Uani 1 1 d . . .
C003 C 0.9752(2) 0.48613(17) 0.66073(16) 0.0439(6) Uani 1 1 d . . .
C004 C 0.7481(2) 0.57871(16) 0.63406(16) 0.0413(6) Uani 1 1 d . . .
C005 C 0.4247(2) 0.66950(15) 0.64260(17) 0.0420(6) Uani 1 1 d . . .
C006 C 0.5869(2) 0.67424(16) 0.51593(18) 0.0454(6) Uani 1 1 d . . .
C007 C 0.5561(2) 0.63057(16) 0.67178(16) 0.0433(6) Uani 1 1 d . . .
C008 C 0.8770(2) 0.45066(17) 0.68644(17) 0.0500(7) Uani 1 1 d . . .
H008 H 0.8860 0.3955 0.7125 0.060 Uiso 1 1 calc R . .
C009 C 0.7664(2) 0.49628(17) 0.67369(17) 0.0473(6) Uani 1 1 d . . .
H009 H 0.7019 0.4715 0.6920 0.057 Uiso 1 1 calc R . .
C00A C 0.3301(2) 0.65358(17) 0.55340(17) 0.0479(6) Uani 1 1 d . . .
H00A H 0.3486 0.6179 0.5090 0.057 Uiso 1 1 calc R . .
C00B C 0.6077(2) 0.59858(16) 0.77495(17) 0.0446(6) Uani 1 1 d . . .
C00C C 0.1786(2) 0.74200(16) 0.59392(18) 0.0464(6) Uani 1 1 d . . .
C00D C 0.2084(2) 0.68959(16) 0.52881(17) 0.0475(6) Uani 1 1 d . . .
H00D H 0.1467 0.6783 0.4682 0.057 Uiso 1 1 calc R . .
C00E C 0.9618(2) 0.56828(17) 0.62347(18) 0.0499(7) Uani 1 1 d . . .
H00E H 1.0281 0.5935 0.6077 0.060 Uiso 1 1 calc R . .
C00F C 0.8487(2) 0.61297(16) 0.60967(17) 0.0489(6) Uani 1 1 d . . .
H00F H 0.8399 0.6679 0.5831 0.059 Uiso 1 1 calc R . .
C00G C 0.5423(2) 0.53911(17) 0.81024(18) 0.0497(7) Uani 1 1 d . . .
H00G H 0.4643 0.5175 0.7688 0.060 Uiso 1 1 calc R . .
C00H C 0.6258(2) 0.62749(16) 0.61205(16) 0.0436(6) Uani 1 1 d . . .
C00I C 0.7028(3) 0.54279(19) 0.97075(18) 0.0559(7) Uani 1 1 d . . .
C00J C 0.5516(2) 0.62721(19) 0.42928(18) 0.0547(7) Uani 1 1 d . . .
H00J H 0.5489 0.5675 0.4318 0.066 Uiso 1 1 calc R . .
C00K C 0.3913(2) 0.72211(17) 0.70742(18) 0.0542(7) Uani 1 1 d . . .
H00K H 0.4524 0.7334 0.7682 0.065 Uiso 1 1 calc R . .
C00L C 0.5899(3) 0.51087(18) 0.90596(19) 0.0564(7) Uani 1 1 d . . .
H00L H 0.5445 0.4695 0.9268 0.068 Uiso 1 1 calc R . .
C00M C 0.2708(3) 0.75773(18) 0.68395(19) 0.0578(7) Uani 1 1 d . . .
H00M H 0.2513 0.7924 0.7287 0.069 Uiso 1 1 calc R . .
C00N C 0.5950(2) 0.76350(18) 0.5122(2) 0.0588(7) Uani 1 1 d . . .
C00O C 0.7217(2) 0.63103(19) 0.84016(18) 0.0572(7) Uani 1 1 d . . .
H00O H 0.7681 0.6716 0.8192 0.069 Uiso 1 1 calc R . .
C00P C 0.7671(2) 0.6036(2) 0.93622(19) 0.0616(8) Uani 1 1 d . . .
H00P H 0.8430 0.6270 0.9787 0.074 Uiso 1 1 calc R . .
C00Q C 0.5642(3) 0.8029(2) 0.4203(3) 0.0749(9) Uani 1 1 d . . .
H00Q H 0.5688 0.8624 0.4164 0.090 Uiso 1 1 calc R . .
C00R C -0.0287(3) 0.7776(2) 0.4818(2) 0.0695(8) Uani 1 1 d . . .
H00B H 0.0075 0.8054 0.4386 0.104 Uiso 1 1 calc R . .
H00C H -0.1059 0.8069 0.4796 0.104 Uiso 1 1 calc R . .
H00H H -0.0485 0.7189 0.4621 0.104 Uiso 1 1 calc R . .
C00S C 0.5278(3) 0.7552(3) 0.3367(3) 0.0797(10) Uani 1 1 d . . .
H00S H 0.5077 0.7826 0.2768 0.096 Uiso 1 1 calc R . .
C00T C 0.5206(3) 0.6676(2) 0.3400(2) 0.0709(9) Uani 1 1 d . . .
H00T H 0.4952 0.6355 0.2828 0.085 Uiso 1 1 calc R . .
C00U C 1.1842(2) 0.4707(2) 0.6508(2) 0.0744(9) Uani 1 1 d . . .
H00I H 1.1554 0.4877 0.5836 0.112 Uiso 1 1 calc R . .
H00N H 1.2516 0.4289 0.6625 0.112 Uiso 1 1 calc R . .
H00R H 1.2162 0.5201 0.6912 0.112 Uiso 1 1 calc R . .
C00V C 0.7530(3) 0.5163(2) 1.0768(2) 0.0826(10) Uani 1 1 d . . .
H00U H 0.7147 0.5519 1.1130 0.124 Uiso 1 1 calc R . .
H00V H 0.8448 0.5230 1.1023 0.124 Uiso 1 1 calc R . .
H00W H 0.7314 0.4573 1.0824 0.124 Uiso 1 1 calc R . .
C00W C 0.6370(3) 0.8172(2) 0.6012(3) 0.0941(11) Uani 1 1 d . . .
H00X H 0.5703 0.8187 0.6290 0.141 Uiso 1 1 calc R . .
H00Y H 0.6543 0.8745 0.5848 0.141 Uiso 1 1 calc R . .
H H 0.7136 0.7932 0.6474 0.141 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 0.0033 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'
Si Si 0.0817 0.0704 '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
C003 O001 C00U 117.1(2) . . ?
C00C O002 C00R 117.2(2) . . ?
O001 C003 C00E 124.5(2) . . ?
O001 C003 C008 116.1(2) . . ?
C00E C003 C008 119.4(2) . . ?
C00F C004 C009 116.5(2) . . ?
C00F C004 C00H 120.0(2) . . ?
C009 C004 C00H 123.4(2) . . ?
C00A C005 C00K 117.0(2) . . ?
C00A C005 C007 122.8(2) . . ?
C00K C005 C007 120.2(2) . . ?
C00N C006 C00J 119.2(3) . . ?
C00N C006 C00H 121.0(2) . . ?
C00J C006 C00H 119.6(2) . . ?
C00H C007 C005 123.1(2) . . ?
C00H C007 C00B 122.3(2) . . ?
C005 C007 C00B 114.6(2) . . ?
C009 C008 C003 120.4(2) . . ?
C009 C008 H008 119.8 . . ?
C003 C008 H008 119.8 . . ?
C008 C009 C004 121.9(2) . . ?
C008 C009 H009 119.1 . . ?
C004 C009 H009 119.1 . . ?
C005 C00A C00D 121.5(2) . . ?
C005 C00A H00A 119.2 . . ?
C00D C00A H00A 119.2 . . ?
C00G C00B C00O 117.2(2) . . ?
C00G C00B C007 122.1(2) . . ?
C00O C00B C007 120.7(2) . . ?
O002 C00C C00D 125.1(2) . . ?
O002 C00C C00M 115.6(2) . . ?
C00D C00C C00M 119.3(2) . . ?
C00C C00D C00A 120.2(2) . . ?
C00C C00D H00D 119.9 . . ?
C00A C00D H00D 119.9 . . ?
C003 C00E C00F 119.5(2) . . ?
C003 C00E H00E 120.3 . . ?
C00F C00E H00E 120.3 . . ?
C00E C00F C004 122.4(2) . . ?
C00E C00F H00F 118.8 . . ?
C004 C00F H00F 118.8 . . ?
C00B C00G C00L 121.6(2) . . ?
C00B C00G H00G 119.2 . . ?
C00L C00G H00G 119.2 . . ?
C007 C00H C004 123.9(2) . . ?
C007 C00H C006 122.9(2) . . ?
C004 C00H C006 113.20(19) . . ?
C00L C00I C00P 117.1(2) . . ?
C00L C00I C00V 122.2(3) . . ?
C00P C00I C00V 120.6(3) . . ?
C00T C00J C006 121.4(3) . . ?
C00T C00J H00J 119.3 . . ?
C006 C00J H00J 119.3 . . ?
C00M C00K C005 121.9(2) . . ?
C00M C00K H00K 119.1 . . ?
C005 C00K H00K 119.1 . . ?
C00I C00L C00G 121.4(3) . . ?
C00I C00L H00L 119.3 . . ?
C00G C00L H00L 119.3 . . ?
C00K C00M C00C 120.1(2) . . ?
C00K C00M H00M 120.0 . . ?
C00C C00M H00M 120.0 . . ?
C006 C00N C00Q 118.3(3) . . ?
C006 C00N C00W 122.2(3) . . ?
C00Q C00N C00W 119.6(3) . . ?
C00P C00O C00B 120.7(3) . . ?
C00P C00O H00O 119.6 . . ?
C00B C00O H00O 119.7 . . ?
C00I C00P C00O 122.0(2) . . ?
C00I C00P H00P 119.0 . . ?
C00O C00P H00P 119.0 . . ?
C00S C00Q C00N 121.2(3) . . ?
C00S C00Q H00Q 119.4 . . ?
C00N C00Q H00Q 119.4 . . ?
O002 C00R H00B 109.5 . . ?
O002 C00R H00C 109.5 . . ?
H00B C00R H00C 109.5 . . ?
O002 C00R H00H 109.5 . . ?
H00B C00R H00H 109.5 . . ?
H00C C00R H00H 109.5 . . ?
C00T C00S C00Q 120.8(3) . . ?
C00T C00S H00S 119.6 . . ?
C00Q C00S H00S 119.6 . . ?
C00S C00T C00J 119.2(3) . . ?
C00S C00T H00T 120.4 . . ?
C00J C00T H00T 120.4 . . ?
O001 C00U H00I 109.5 . . ?
O001 C00U H00N 109.5 . . ?
H00I C00U H00N 109.5 . . ?
O001 C00U H00R 109.5 . . ?
H00I C00U H00R 109.5 . . ?
H00N C00U H00R 109.5 . . ?
C00I C00V H00U 109.5 . . ?
C00I C00V H00V 109.5 . . ?
H00U C00V H00V 109.5 . . ?
C00I C00V H00W 109.5 . . ?
H00U C00V H00W 109.5 . . ?
H00V C00V H00W 109.5 . . ?
C00N C00W H00X 109.5 . . ?
C00N C00W H00Y 109.5 . . ?
H00X C00W H00Y 109.5 . . ?
C00N C00W H 109.5 . . ?
H00X C00W H 109.5 . . ?
H00Y C00W H 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 C003 1.370(3) . ?
O001 C00U 1.421(3) . ?
O002 C00C 1.375(3) . ?
O002 C00R 1.415(3) . ?
C003 C00E 1.377(3) . ?
C003 C008 1.383(3) . ?
C004 C00F 1.389(3) . ?
C004 C009 1.393(3) . ?
C004 C00H 1.488(3) . ?
C005 C00A 1.386(3) . ?
C005 C00K 1.396(3) . ?
C005 C007 1.496(3) . ?
C006 C00N 1.394(4) . ?
C006 C00J 1.398(3) . ?
C006 C00H 1.509(3) . ?
C007 C00H 1.353(3) . ?
C007 C00B 1.503(3) . ?
C008 C009 1.371(3) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C00A C00D 1.388(3) . ?
C00A H00A 0.9300 . ?
C00B C00G 1.381(3) . ?
C00B C00O 1.389(3) . ?
C00C C00D 1.378(3) . ?
C00C C00M 1.382(3) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.385(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G C00L 1.387(3) . ?
C00G H00G 0.9300 . ?
C00I C00L 1.376(4) . ?
C00I C00P 1.380(4) . ?
C00I C00V 1.515(4) . ?
C00J C00T 1.383(4) . ?
C00J H00J 0.9300 . ?
C00K C00M 1.375(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00Q 1.410(4) . ?
C00N C00W 1.481(4) . ?
C00O C00P 1.387(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q C00S 1.368(4) . ?
C00Q H00Q 0.9300 . ?
C00R H00B 0.9600 . ?
C00R H00C 0.9600 . ?
C00R H00H 0.9600 . ?
C00S C00T 1.367(4) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00I 0.9600 . ?
C00U H00N 0.9600 . ?
C00U H00R 0.9600 . ?
C00V H00U 0.9600 . ?
C00V H00V 0.9600 . ?
C00V H00W 0.9600 . ?
C00W H00X 0.9600 . ?
C00W H00Y 0.9600 . ?
C00W H 0.9600 . ?
