Synthesis and Rhodium(II)-Mediated Cascade Cyclopropanation/Rearrangement/Isomerization of Diazo 2,3,5-Trisubstituted Furans: the Construction of Pentasubstituted Aromatic Compounds.
Zhang, Jianfang; Yang, Qin; Zhu, Yang; Wang, Jianbo; Deng, Guisheng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03093

data_4037826
_publ_section_title
;
 Synthesis and Rhodium(II)-Mediated Cascade
 Cyclopropanation/Rearrangement/Isomerization of Diazo
 2,3,5-Trisubstituted Furans: the Construction of Pentasubstituted
 Aromatic Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03093
_journal_year                    2020
_chemical_formula_moiety         'C24 H21 Cl O4'
_chemical_formula_sum            'C24 H21 Cl O4'
_chemical_formula_weight         408.86
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.303(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.621(6)
_cell_length_b                   10.647(3)
_cell_length_c                   16.385(4)
_cell_measurement_reflns_used    8160
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      3.22
_cell_volume                     4113.9(19)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16152
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.8079.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0641P)^2^+3.5087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03093_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        4113.8(18)
_cod_database_code               4037826
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.815
_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. Restrained distances
 O4A-C23A = O4-C23
 1.43 with sigma of 0.02
 C24-C23 = C23A-C24A
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C23A)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C24A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Sof(O4)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=1-
 FVAR(1)
 Sof(O4A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B), C23A(H23C,H23D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C11(H11), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'