A tunable copper-catalyzed multicomponent reaction towards alkaloid-inspired indole/lactam polycycles.
Mardjan, M. I. D.; Perie, S.; Parrain, J.-L.; Commeiras, L.; Organic & biomolecular chemistry 15 (2017) 3304–3309; doi:10.1039/c7ob00532f

data_7155540
_publ_section_title
;
 A tunable copper-catalyzed multicomponent reaction towards
 alkaloid-inspired indole/lactam polycycles.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3304
_journal_page_last               3309
_journal_paper_doi               10.1039/c7ob00532f
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         '2(C20 H24 N2 O)'
_chemical_formula_sum            'C40 H48 N4 O2'
_chemical_formula_weight         616.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-12-24 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.062(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7853(6)
_cell_length_b                   15.0292(8)
_cell_length_c                   19.3138(13)
_cell_measurement_reflns_used    5324
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3640
_cell_measurement_theta_min      4.1280
_cell_volume                     3547.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
  1 omega   31.00   69.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629 -160.0000  -96.0000 38

  2 omega    6.00   51.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -99.0000 -180.0000 45

  3 omega  -13.00   43.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   38.0000  120.0000 56

  4 omega  -11.00   15.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -38.0000    0.0000 26

  5 omega  -33.00   35.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -57.0000 -120.0000 68

  6 omega  -31.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   19.0000   30.0000 121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0141888000
_diffrn_orient_matrix_UB_12      0.0069509000
_diffrn_orient_matrix_UB_13      0.0379498000
_diffrn_orient_matrix_UB_21      0.0086361000
_diffrn_orient_matrix_UB_22      -0.0463668000
_diffrn_orient_matrix_UB_23      0.0058139000
_diffrn_orient_matrix_UB_31      0.0556014000
_diffrn_orient_matrix_UB_32      0.0054439000
_diffrn_orient_matrix_UB_33      0.0011641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.040
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.155
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8219
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0488P)^2^+1.9298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4579
_reflns_number_total             8219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00532f2.cif
_cod_data_source_block           idh502
_cod_depositor_comments
'Adding full bibliography for 7155539--7155540.cif.'
_cod_original_cell_volume        3547.8(4)
_cod_database_code               7155540
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C233
 1.54 with sigma of 0.005
 C22-C233
 1.54 with sigma of 0.005
 C22-C23
 1.54 with sigma of 0.005
 C24-C23
 1.54 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C233)
4. Others
 Sof(H22C)=Sof(H22D)=Sof(H24C)=Sof(H24D)=Sof(C233)=Sof(H23C)=Sof(H23D)=1-FVAR(1)
 Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H24A)=Sof(H24B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B), C0AA(H0AA,H0AB), C22(H22A,H22B), C22(H22C,H22D), C23(H23A,
 H23B), C24(H24A,H24B), C24(H24C,H24D), C37(H37A,H37B), C38(H38A,H38B),
 C233(H23C,H23D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), N3(H3), C27(H27),
 C28(H28), C29(H29), C30(H30), C34(H34)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C36(H36A,H36B,H36C), C39(H39A,H39B,
 H39C)
;
_olex2_submission_special_instructions 'No special instructions were received'