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_7155539
_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         'C22 H20 N2 O, C2 H6 O'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-12-24 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.253(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4563(5)
_cell_length_b                   18.7494(8)
_cell_length_c                   9.4799(3)
_cell_measurement_reflns_used    8643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9820
_cell_measurement_theta_min      4.1620
_cell_volume                     2036.25(14)
_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, 2008)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
  1 omega  -84.00  -53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  153.0000    1.4328 31

  2 omega  -20.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  -99.0000 -180.0000 51

  3 omega  -84.00  -55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.6629  153.0000  -76.6376 29

  4 omega  -15.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   38.0000   30.0000 98

  5 omega  -18.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348   57.0000  120.0000 101

  6 omega  -20.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348  -99.0000  -60.0000 71

  7 omega  -71.00   73.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348    0.0000  -30.0000 144

  8 omega    0.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8348 -113.0000 -165.1299 59
;
_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      0.0290749000
_diffrn_orient_matrix_UB_12      -0.0278650000
_diffrn_orient_matrix_UB_13      -0.0362471000
_diffrn_orient_matrix_UB_21      0.0539447000
_diffrn_orient_matrix_UB_22      0.0180011000
_diffrn_orient_matrix_UB_23      0.0092896000
_diffrn_orient_matrix_UB_31      0.0088427000
_diffrn_orient_matrix_UB_32      -0.0181852000
_diffrn_orient_matrix_UB_33      0.0647909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30771
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.075
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91379
_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    1.222
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0685P)^2^+1.0141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             4900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00532f2.cif
_cod_data_source_block           1dh444
_cod_depositor_comments
'Adding full bibliography for 7155539--7155540.cif.'
_cod_original_cell_volume        2036.23(13)
_cod_database_code               7155539
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.66
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_olex2_submission_special_instructions 'No special instructions were received'