Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study
Fan, Qiangwen; Tan, Hongbo; Li, Peng; Yan, Hong; New Journal of Chemistry 42 (2018) 16795–; doi:10.1039/C8NJ02192A

data_7057722
_publ_section_title
;
 Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a
 combined experimental and DFT study
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16795
_journal_paper_doi               10.1039/C8NJ02192A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C37 H42 N2 O11'
_chemical_formula_sum            'C37 H42 N2 O11'
_chemical_formula_weight         690.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             16-05-26
_audit_creation_method
;
Rigaku CrystalClear-SM Expert 2.1 b42
;
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                88.088(9)
_cell_angle_beta                 75.632(7)
_cell_angle_gamma                76.611(7)
_cell_formula_units_Z            4
_cell_length_a                   10.9132(13)
_cell_length_b                   16.828(2)
_cell_length_c                   21.963(3)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3799.8(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_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      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.0040
              2theta: -15.0627
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.0040
              2theta: -15.0627
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0040
              2theta: -15.0627
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.078108
_diffrn_orient_matrix_UB_12      0.057411
_diffrn_orient_matrix_UB_13      0.007294
_diffrn_orient_matrix_UB_21      -0.004568
_diffrn_orient_matrix_UB_22      -0.024722
_diffrn_orient_matrix_UB_23      0.055693
_diffrn_orient_matrix_UB_31      0.017094
_diffrn_orient_matrix_UB_32      -0.040977
_diffrn_orient_matrix_UB_33      -0.015469
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            48769
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1464
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     924
_refine_ls_number_reflns         17104
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0830P)^2^+5.3487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11650
_reflns_number_total             17104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj02192a2.cif
_cod_data_source_block           shelx_sq
_cod_depositor_comments
'Adding full bibliography for 7057720--7057722.cif.'
_cod_original_cell_volume        3799.9(9)
_cod_database_code               7057722
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.980
_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. Shared sites
{C73, C73'}
3. Restrained distances
 C73-C74 = C73'-C74'
 1.54 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C73 \\sim C74 \\sim C73' \\sim C74': within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C73) \\sim Ueq, Uanis(C74) \\sim Ueq, Uanis(C73') \\sim Ueq, Uanis(C74')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C73) = Uanis(C73')
5. Others
 Sof(C73')=Sof(H73C)=Sof(H73D)=Sof(C74')=Sof(H74D)=Sof(H74E)=Sof(H74F)=1-FVAR(1)
 Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C40(H40), C42(H42), C44(H44), C47(H47)
6.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B), C33(H33A,H33B), C36(H36A,H36B), C55(H55A,
 H55B), C58(H58A,H58B), C70(H70A,H70B), C73(H73A,H73B), C73'(H73C,H73D)
6.c Me refined with riding coordinates:
 C74(H74A,H74B,H74C), C74'(H74D,H74E,H74F)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C24(H24),
 C28(H28), C38(H38), C45(H45), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53),
  C61(H61), C65(H65)
6.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C), C56(H56A,
 H56B,H56C), C59(H59A,H59B,H59C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C),
 C68(H68A,H68B,H68C), C71(H71A,H71B,H71C)
;
_shelx_res_checksum              95352
_shelx_fab_checksum              64544
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'