Csp-Csp(3) Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes.
Shen, Yangyong; Huang, Bo; Zheng, Jing; Lin, Chen; Liu, Yu; Cui, Sunliang; Organic letters 19 (2017) 1744–1747; doi:10.1021/acs.orglett.7b00499

data_1545941
_publ_section_title
;
 Csp-Csp(3) Bond Formation via Iron(III)-Promoted Hydroalkynylation of
 Unactivated Alkenes.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1744
_journal_page_last               1747
_journal_paper_doi               10.1021/acs.orglett.7b00499
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C12 H13 Cl O'
_chemical_formula_sum            'C12 H13 Cl O'
_chemical_formula_weight         208.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 134.78
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   39.96(3)
_cell_length_b                   11.468(9)
_cell_length_c                   28.37(2)
_cell_measurement_reflns_used    2958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.830
_cell_measurement_theta_min      2.390
_cell_volume                     9228(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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(2)
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_unetI/netI     0.1324
_diffrn_reflns_Laue_measured_fraction_full 0.873
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23091
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.782
_diffrn_reflns_theta_min         1.436
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1463 before and 0.0851 after correction.
The Ratio of minimum to maximum transmission is 0.7008.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             3520
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.1729
_refine_ls_R_factor_gt           0.0589
_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/[\s^2^(Fo^2^)+(0.0463P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2785
_reflns_number_total             7720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00499_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        9229(12)
_cod_database_code               1545941
_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:
 C013(H01Y,H), C015(H01I,H01J), C01C(H01D,H01E), C01D(H01Q,H01R)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00V(H00V), C00X(H00X), C00Y(H00Y), C010(H010)
2.c Idealised Me refined as rotating group:
 C017(H01K,H01L,H01M), C019(H01A,H01B,H01C), C01E(H01Z,HA,HB), C01G(H01S,H01T,
 H01U), C01H(H01F,H01G,H01H), C01I(H01N,H01O,H01P), C01J(H01V,H01W,H01X),
 C01K(H01,HC,HD)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005), O006(H006), O007(H007), O008(H008)
;
_shelx_res_checksum              74873
_shelx_hkl_checksum              70359
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'