#------------------------------------------------------------------------------
#$Date: 2019-02-20 01:20:28 +0200 (Wed, 20 Feb 2019) $
#$Revision: 213712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/06/1550627.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_1550627
loop_
_publ_author_name
'Ye, Changqing'
'Li, Yajun'
'Zhu, Xiaotao'
'Hu, Shengmin'
'Yuan, Daqiang'
'Bao, Hongli'
_publ_section_title
;
 Copper-Catalyzed 1,4-Alkylarylation of 1,3-Enynes with Masked Alkyl
 Electrophiles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05689G
_journal_year                    2019
_chemical_formula_sum            'C44 H46 O4'
_chemical_formula_weight         638.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-12-04 deposited with the CCDC.    2019-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                76.980(4)
_cell_angle_beta                 84.293(3)
_cell_angle_gamma                86.909(3)
_cell_formula_units_Z            2
_cell_length_a                   10.8484(4)
_cell_length_b                   11.0591(5)
_cell_length_c                   15.2489(6)
_cell_measurement_reflns_used    16446
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      60.3760
_cell_measurement_theta_min      2.5820
_cell_volume                     1772.66(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      99.99(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24617
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.549
_diffrn_reflns_theta_min         2.596
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       prism
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0449
_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)+(0.0622P)²+0.5622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6775
_reflns_number_total             7932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc05689g2.cif
_cod_data_source_block           Compound-18
_cod_database_code               1550627
_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.
;
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
O1 O 0.26564(10) 0.13322(10) 0.88722(7) 0.0358(2) Uani 1 1 d . .
O2 O 0.12821(9) 0.22827(10) 0.79230(7) 0.0352(2) Uani 1 1 d . .
O3 O -0.04059(10) 0.37836(11) 0.12466(8) 0.0422(3) Uani 1 1 d . .
O4 O -0.04845(9) 0.22001(10) 0.05721(7) 0.0340(2) Uani 1 1 d . .
C1 C 0.02717(15) 0.50031(17) 0.30423(12) 0.0422(4) Uani 1 1 d . .
H1A H -0.040066 0.541801 0.332693 0.063 Uiso 1 1 calc R U
H1B H 0.001372 0.420741 0.298998 0.063 Uiso 1 1 calc R U
H1C H 0.050839 0.549497 0.245157 0.063 Uiso 1 1 calc R U
C2 C 0.13597(13) 0.48287(13) 0.36046(9) 0.0281(3) Uani 1 1 d . .
C3 C 0.24030(13) 0.41173(12) 0.34056(9) 0.0270(3) Uani 1 1 d . .
H3 H 0.242817 0.373445 0.291976 0.032 Uiso 1 1 calc R U
C4 C 0.34097(12) 0.39705(12) 0.39234(8) 0.0236(3) Uani 1 1 d . .
H4 H 0.409491 0.349031 0.377380 0.028 Uiso 1 1 calc R U
C5 C 0.34219(11) 0.45202(11) 0.46574(8) 0.0211(2) Uani 1 1 d . .
C6 C 0.23649(12) 0.52280(11) 0.48598(9) 0.0237(3) Uani 1 1 d . .
H6 H 0.233322 0.560179 0.535062 0.028 Uiso 1 1 calc R U
C7 C 0.13648(12) 0.53800(12) 0.43397(9) 0.0271(3) Uani 1 1 d . .
H7 H 0.067998 0.586293 0.448603 0.032 Uiso 1 1 calc R U
C8 C 0.45663(11) 0.44012(11) 0.51958(8) 0.0209(2) Uani 1 1 d . .
C9 C 0.42028(12) 0.43014(11) 0.62168(8) 0.0223(3) Uani 1 1 d . .
H9A H 0.495513 0.420099 0.652410 0.027 Uiso 1 1 calc R U
H9B H 0.379563 0.507744 0.629520 0.027 Uiso 1 1 calc R U
C10 C 0.33551(12) 0.32436(12) 0.66737(8) 0.0238(3) Uani 1 1 d . .
H10A H 0.368096 0.247619 0.652011 0.029 Uiso 1 1 calc R U
H10B H 0.253646 0.341542 0.646128 0.029 Uiso 1 1 calc R U
C11 C 0.32664(13) 0.31035(14) 0.76989(9) 0.0307(3) Uani 1 1 d . .
H11A H 0.408869 0.290560 0.790015 0.037 Uiso 1 1 calc R U
H11B H 0.299785 0.389712 0.783524 0.037 Uiso 1 1 calc R U
C12 C 0.24027(13) 0.21304(13) 0.82338(8) 0.0262(3) Uani 1 1 d . .
C13 C 0.03378(15) 0.14534(16) 0.84054(11) 0.0402(4) Uani 1 1 d . .
H13A H 0.052432 0.063486 0.830376 0.060 Uiso 1 1 calc R U
H13B H -0.045280 0.174352 0.819362 0.060 Uiso 1 1 calc R U
H13C H 0.031315 0.142955 0.904015 0.060 Uiso 1 1 calc R U
C14 C 0.53235(12) 0.32867(11) 0.50849(8) 0.0220(2) Uani 1 1 d . .
C15 C 0.59763(12) 0.24147(11) 0.49810(8) 0.0227(3) Uani 1 1 d . .
C16 C 0.68196(12) 0.14206(12) 0.48188(9) 0.0228(3) Uani 1 1 d . .
C17 C 0.65918(14) 0.01857(12) 0.52333(9) 0.0290(3) Uani 1 1 d . .
H17 H 0.588773 -0.000704 0.563170 0.035 Uiso 1 1 calc R U
C18 C 0.74075(15) -0.07591(13) 0.50563(10) 0.0326(3) Uani 1 1 d . .
H18 H 0.723901 -0.157701 0.534075 0.039 Uiso 1 1 calc R U
C19 C 0.84645(14) -0.05143(14) 0.44675(10) 0.0320(3) Uani 1 1 d . .
C20 C 0.86943(13) 0.07223(15) 0.40539(12) 0.0368(3) Uani 1 1 d . .
H20 H 0.940207 0.091159 0.365875 0.044 Uiso 1 1 calc R U
C21 C 0.78829(13) 0.16742(13) 0.42230(11) 0.0317(3) Uani 1 1 d . .
H21 H 0.805021 0.249125 0.393555 0.038 Uiso 1 1 calc R U
C22 C 0.93293(17) -0.15576(17) 0.42776(13) 0.0463(4) Uani 1 1 d . .
H22A H 0.910186 -0.231740 0.469451 0.069 Uiso 1 1 calc R U
H22B H 1.016456 -0.137410 0.434641 0.069 Uiso 1 1 calc R U
H22C H 0.927194 -0.164532 0.367091 0.069 Uiso 1 1 calc R U
C23 C 0.60148(13) 0.01746(12) 0.28289(9) 0.0280(3) Uani 1 1 d . .
H23A H 0.542194 -0.045596 0.287645 0.042 Uiso 1 1 calc R U
H23B H 0.608859 0.032633 0.341679 0.042 Uiso 1 1 calc R U
H23C H 0.680540 -0.009788 0.258717 0.042 Uiso 1 1 calc R U
C24 C 0.55900(11) 0.13506(12) 0.22129(8) 0.0227(3) Uani 1 1 d . .
C25 C 0.55756(12) 0.24960(12) 0.24500(8) 0.0238(3) Uani 1 1 d . .
H25 H 0.582595 0.253864 0.300776 0.029 Uiso 1 1 calc R U
C26 C 0.51926(12) 0.35789(12) 0.18657(8) 0.0224(3) Uani 1 1 d . .
H26 H 0.518742 0.433151 0.204196 0.027 Uiso 1 1 calc R U
C27 C 0.48177(11) 0.35559(11) 0.10235(8) 0.0193(2) Uani 1 1 d . .
C28 C 0.48215(11) 0.23995(11) 0.07909(8) 0.0211(2) Uani 1 1 d . .
H28 H 0.456227 0.235241 0.023659 0.025 Uiso 1 1 calc R U
C29 C 0.52070(11) 0.13212(11) 0.13766(8) 0.0226(3) Uani 1 1 d . .
H29 H 0.520820 0.056612 0.120430 0.027 Uiso 1 1 calc R U
C30 C 0.44229(11) 0.47529(11) 0.03656(8) 0.0191(2) Uani 1 1 d . .
C31 C 0.32987(11) 0.45129(11) -0.01192(8) 0.0213(2) Uani 1 1 d . .
H31A H 0.309955 0.526092 -0.055938 0.026 Uiso 1 1 calc R U
H31B H 0.352767 0.386211 -0.044347 0.026 Uiso 1 1 calc R U
C32 C 0.21476(12) 0.41336(13) 0.05284(9) 0.0247(3) Uani 1 1 d . .
H32A H 0.239548 0.357455 0.107374 0.030 Uiso 1 1 calc R U
H32B H 0.175177 0.486599 0.069700 0.030 Uiso 1 1 calc R U
C33 C 0.12206(12) 0.34970(13) 0.01098(9) 0.0266(3) Uani 1 1 d . .
H33A H 0.102030 0.403367 -0.045786 0.032 Uiso 1 1 calc R U
H33B H 0.160096 0.273549 -0.002084 0.032 Uiso 1 1 calc R U
C34 C 0.00448(12) 0.31959(13) 0.07123(9) 0.0272(3) Uani 1 1 d . .
C35 C -0.16678(14) 0.19058(15) 0.10802(11) 0.0379(3) Uani 1 1 d . .
H35A H -0.158595 0.182969 0.171162 0.057 Uiso 1 1 calc R U
H35B H -0.193726 0.113608 0.098555 0.057 Uiso 1 1 calc R U
H35C H -0.226636 0.255622 0.088116 0.057 Uiso 1 1 calc R U
C36 C 0.40343(11) 0.57405(11) 0.08533(8) 0.0208(2) Uani 1 1 d . .
C37 C 0.36551(11) 0.65777(11) 0.11958(8) 0.0220(2) Uani 1 1 d . .
C38 C 0.32265(11) 0.76516(11) 0.15402(8) 0.0214(2) Uani 1 1 d . .
C39 C 0.30206(12) 0.87879(12) 0.09318(9) 0.0242(3) Uani 1 1 d . .
H39 H 0.316222 0.883907 0.031309 0.029 Uiso 1 1 calc R U
C40 C 0.26088(12) 0.98297(12) 0.12474(9) 0.0256(3) Uani 1 1 d . .
H40 H 0.246528 1.057164 0.083592 0.031 Uiso 1 1 calc R U
C41 C 0.24043(12) 0.97904(12) 0.21705(9) 0.0253(3) Uani 1 1 d . .
C42 C 0.26095(12) 0.86617(13) 0.27691(9) 0.0259(3) Uani 1 1 d . .
H42 H 0.247544 0.861693 0.338733 0.031 Uiso 1 1 calc R U
C43 C 0.30096(12) 0.76009(12) 0.24655(9) 0.0247(3) Uani 1 1 d . .
H43 H 0.313305 0.685606 0.287896 0.030 Uiso 1 1 calc R U
C44 C 0.19967(15) 1.09490(13) 0.24990(10) 0.0338(3) Uani 1 1 d . .
H44A H 0.177781 1.073627 0.313937 0.051 Uiso 1 1 calc R U
H44B H 0.129105 1.132967 0.219835 0.051 Uiso 1 1 calc R U
H44C H 0.266185 1.151908 0.236858 0.051 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 0.0137 0.0067 '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 0.0389 0.0241 '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_3
C12 O2 C13 117.10(11) .
C34 O4 C35 115.21(11) .
C3 C2 C7 117.39(13) .
C3 C2 C1 121.28(13) .
C7 C2 C1 121.33(13) .
C2 C3 C4 120.92(13) .
C5 C4 C3 121.99(12) .
C4 C5 C6 116.90(12) .
C4 C5 C8 121.39(11) .
C6 C5 C8 121.66(11) .
C7 C6 C5 121.06(12) .
C6 C7 C2 121.74(12) .
C14 C8 C5 110.02(10) .
C14 C8 C9 108.47(10) .
C5 C8 C9 111.99(10) .
C14 C8 C8 107.18(12) 2_666
C5 C8 C8 109.82(12) 2_666
C9 C8 C8 109.24(12) 2_666
C10 C9 C8 115.34(10) .
C9 C10 C11 109.73(11) .
C12 C11 C10 115.33(11) .
O1 C12 O2 123.39(13) .
O1 C12 C11 125.46(13) .
O2 C12 C11 111.13(11) .
C15 C14 C8 177.33(13) .
C14 C15 C16 176.22(13) .
C17 C16 C21 118.13(12) .
C17 C16 C15 121.51(12) .
C21 C16 C15 120.35(12) .
C18 C17 C16 120.54(13) .
C19 C18 C17 121.64(13) .
C18 C19 C20 117.84(13) .
C18 C19 C22 120.69(15) .
C20 C19 C22 121.47(15) .
C21 C20 C19 121.02(14) .
C20 C21 C16 120.82(13) .
C29 C24 C25 117.89(11) .
C29 C24 C23 120.22(12) .
C25 C24 C23 121.89(12) .
C24 C25 C26 121.11(12) .
C27 C26 C25 121.23(12) .
C26 C27 C28 117.50(11) .
C26 C27 C30 121.50(11) .
C28 C27 C30 121.00(11) .
C29 C28 C27 121.00(11) .
C24 C29 C28 121.26(12) .
C36 C30 C27 110.90(10) .
C36 C30 C31 107.20(10) .
C27 C30 C31 110.21(9) .
C36 C30 C30 108.06(11) 2_665
C27 C30 C30 109.89(11) 2_665
C31 C30 C30 110.54(12) 2_665
C32 C31 C30 113.16(10) .
C33 C32 C31 112.08(11) .
C34 C33 C32 112.85(11) .
O3 C34 O4 122.71(13) .
O3 C34 C33 125.29(13) .
O4 C34 C33 111.98(12) .
C37 C36 C30 174.68(13) .
C36 C37 C38 175.43(13) .
C43 C38 C39 118.65(11) .
C43 C38 C37 121.92(11) .
C39 C38 C37 119.43(11) .
C40 C39 C38 120.40(12) .
C39 C40 C41 121.31(12) .
C42 C41 C40 117.97(12) .
C42 C41 C44 121.68(12) .
C40 C41 C44 120.34(12) .
C43 C42 C41 121.61(12) .
C42 C43 C38 120.06(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.2011(16) .
O2 C12 1.3370(17) .
O2 C13 1.4419(17) .
O3 C34 1.2044(17) .
O4 C34 1.3367(16) .
O4 C35 1.4449(17) .
C1 C2 1.506(2) .
C2 C3 1.3912(19) .
C2 C7 1.392(2) .
C3 C4 1.3917(19) .
C4 C5 1.3903(18) .
C5 C6 1.4017(17) .
C5 C8 1.5391(18) .
C6 C7 1.3878(19) .
C8 C14 1.4764(16) .
C8 C9 1.5481(16) .
C8 C8 1.632(2) 2_666
C9 C10 1.5235(17) .
C10 C11 1.5297(18) .
C11 C12 1.5042(18) .
C14 C15 1.1956(18) .
C15 C16 1.4407(17) .
C16 C17 1.3936(18) .
C16 C21 1.3951(19) .
C17 C18 1.3883(19) .
C18 C19 1.383(2) .
C19 C20 1.395(2) .
C19 C22 1.5083(19) .
C20 C21 1.388(2) .
C23 C24 1.5024(17) .
C24 C29 1.3876(18) .
C24 C25 1.3923(18) .
C25 C26 1.3928(17) .
C26 C27 1.3911(18) .
C27 C28 1.4018(17) .
C27 C30 1.5389(16) .
C28 C29 1.3912(17) .
C30 C36 1.4757(17) .
C30 C31 1.5513(16) .
C30 C30 1.622(2) 2_665
C31 C32 1.5282(16) .
C32 C33 1.5235(18) .
C33 C34 1.5023(18) .
C36 C37 1.1972(18) .
C37 C38 1.4406(17) .
C38 C43 1.3961(18) .
C38 C39 1.4055(17) .
C39 C40 1.3821(18) .
C40 C41 1.3943(19) .
C41 C42 1.3920(19) .
C41 C44 1.5074(18) .
C42 C43 1.3888(18) .
