Intermolecular [2 + 2] Cycloaddition of 1,4-Dihydropyridines with Olefins via Energy Transfer.
Wang, Chengfeng; Lu, Zhan; Organic letters 19 (2017) 5888–5891; doi:10.1021/acs.orglett.7b02881

data_1547736
_publ_section_title
;
 Intermolecular [2 + 2] Cycloaddition of 1,4-Dihydropyridines with Olefins
 via Energy Transfer.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5888
_journal_page_last               5891
_journal_paper_doi               10.1021/acs.orglett.7b02881
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H37 N O4'
_chemical_formula_sum            'C31 H37 N O4'
_chemical_formula_weight         487.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-24
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Olex2 1.2
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_cell_length_b                   15.3140(13)
_cell_length_c                   11.5062(13)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    170.1
_cell_measurement_theta_max      29.3370
_cell_measurement_theta_min      3.0320
_cell_volume                     1314.1(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.1
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -38.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  120.0000 88

  2 omega  -66.00   21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -72.0000 -176.0000 87

  3 omega  -87.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -60.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0107604000
_diffrn_orient_matrix_UB_12      -0.0134367000
_diffrn_orient_matrix_UB_13      -0.0586860000
_diffrn_orient_matrix_UB_21      -0.0562463000
_diffrn_orient_matrix_UB_22      -0.0347068000
_diffrn_orient_matrix_UB_23      0.0177691000
_diffrn_orient_matrix_UB_31      -0.0760105000
_diffrn_orient_matrix_UB_32      0.0275464000
_diffrn_orient_matrix_UB_33      -0.0062727000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.0820
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_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8066
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         3.038
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38775
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0919
_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^)+(0.1795P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2381
_refine_ls_wR_factor_ref         0.2705
_reflns_Friedel_coverage         0.664
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_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                3185
_reflns_number_total             4152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02881_si_005.cif
_cod_data_source_block           170720_wcf12008
_cod_depositor_comments
'Adding full bibliography for 1547735--1547738.cif.'
_cod_database_code               1547736
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.75
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B),
 C20(H20A,H20B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              9724
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_olex2_submission_special_instructions 'No special instructions were received'