Benzene Construction via Pd-catalyzed Cyclization of 2,7-Alkadiynylic Carbonates in the Presence of Alkynes
Zhang, Yuchen; Wu, Wangteng; Fu, Chunling; Huang, Xin; Ma, Shengming; Chemical Science  (2019) –; doi:10.1039/C8SC04681F

data_1550377
_publ_section_title
;
 Benzene Construction via Pd-catalyzed Cyclization of 2,7-Alkadiynylic
 Carbonates in the Presence of Alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC04681F
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 O2'
_chemical_formula_sum            'C24 H22 O2'
_chemical_formula_weight         342.41
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20268l
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-13 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.932(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8864(5)
_cell_length_b                   33.272(3)
_cell_length_c                   8.5011(8)
_cell_measurement_reflns_used    1931
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2773
_cell_measurement_theta_min      3.0551
_cell_volume                     1882.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -34.00   64.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000   90.0000 98

  2 omega    8.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000    0.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0217074000
_diffrn_orient_matrix_UB_12      0.0077296000
_diffrn_orient_matrix_UB_13      0.0804368000
_diffrn_orient_matrix_UB_21      -0.0677412000
_diffrn_orient_matrix_UB_22      0.0160971000
_diffrn_orient_matrix_UB_23      -0.0273782000
_diffrn_orient_matrix_UB_31      -0.0793860000
_diffrn_orient_matrix_UB_32      -0.0116370000
_diffrn_orient_matrix_UB_33      0.0154950000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7378
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1457
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2370
_reflns_number_total             3441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04681f2.cif
_cod_data_source_block           180604_zyc_2_35
_cod_database_code               1550377
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.52
_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:
 C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              26636
_olex2_submission_special_instructions 'No special instructions were received'