E-Selective N-heterocyclic carbene-catalyzed reaction of aldehydes and butadienoates: effect of water and chloroform as the proton shuttle
Ma, Dengke; Song, Yulong; Fu, Chunling; Zhang, Fang; Guo, Yinlong; Huang, Xin; Ma, Shengming; Organic Chemistry Frontiers 5 (2018) 2560–; doi:10.1039/C8QO00579F

data_1554370
_publ_section_title
;
 E-Selective N-heterocyclic carbene-catalyzed reaction of aldehydes and
 butadienoates: effect of water and chloroform as the proton shuttle
;
_journal_issue                   17
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2560
_journal_paper_doi               10.1039/C8QO00579F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_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             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-03-24 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.416(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7223(19)
_cell_length_b                   5.7888(4)
_cell_length_c                   25.159(2)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5109
_cell_measurement_theta_min      3.1602
_cell_volume                     3294.5(4)
_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    'ShelXS (Sheldrick, 2008)'
_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  -37.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   38.0000  120.0000 83

  2 omega  -32.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   77.0000  -30.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0274168000
_diffrn_orient_matrix_UB_12      -0.0488457000
_diffrn_orient_matrix_UB_13      -0.0054160000
_diffrn_orient_matrix_UB_21      -0.0035566000
_diffrn_orient_matrix_UB_22      0.0469807000
_diffrn_orient_matrix_UB_23      -0.0261468000
_diffrn_orient_matrix_UB_31      0.0147575000
_diffrn_orient_matrix_UB_32      0.1021404000
_diffrn_orient_matrix_UB_33      0.0094411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6328
_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         25.350
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92172
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0774P)^2^+0.2794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2071
_reflns_number_total             2997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00579f2.cif
_cod_data_source_block           170301_mdk_11_043_3
_cod_original_cell_volume        3294.6(5)
_cod_database_code               1554370
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.49
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              88594
_shelx_hkl_checksum              17460
_olex2_submission_special_instructions 'No special instructions were received'