Diverse privileged <i>N</i>-polycyclic skeletons accessed from a metal-free cascade cyclization reaction.
Li, Wenzhong; Wang, Yu; Qi, Huijing; Shi, Ran; Li, Jiazhu; Chen, Si; Xu, Xin-Ming; Wang, Wei-Li; Organic & biomolecular chemistry 19 (2021) 8086–8095; doi:10.1039/d1ob01206a

data_7158250
_publ_section_title
;
 Diverse privileged <i>N</i>-polycyclic skeletons accessed from a
 metal-free cascade cyclization reaction.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8086
_journal_page_last               8095
_journal_paper_doi               10.1039/d1ob01206a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-04 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.04690(10)
_cell_length_b                   10.3794(2)
_cell_length_c                   16.3300(3)
_cell_measurement_reflns_used    30427
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.9420
_cell_measurement_theta_min      2.2940
_cell_volume                     1702.91(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -84.00  94.00   0.50    2.00    --    5.00  45.00  90.00  356
  2  \w    -19.00  48.00   0.50    2.00    --    5.00  45.00  60.00  134
  3  \w    -54.00 -28.00   0.50    2.00    --    5.00  45.00 150.00   52
  4  \w    -10.00  60.00   0.50    2.00    --    5.00  45.00 120.00  140
  5  \w     19.00  56.00   0.50    2.00    --    5.00  45.00  90.00   74
  6  \w      5.00  31.00   0.50    2.00    --    5.00  45.00  30.00   52
  7  \w     62.00  94.00   0.50    2.00    --    5.00  45.00  30.00   64
  8  \w   -101.00  77.00   0.50    2.00    --  -11.60  45.00 150.00  356
  9  \w     37.00  63.00   0.50    2.00    --  -11.60  45.00 -18.31   52
 10  \w   -101.00 -35.00   0.50    2.00    --  -11.60  45.00 -18.31  132
 11  \w     25.00  53.00   0.50    2.00    --  -11.60  45.00  87.70   56
 12  \w    -98.00  19.00   0.50    2.00    --  -11.60  45.00  87.70  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0396808000
_diffrn_orient_matrix_UB_12      -0.0268604000
_diffrn_orient_matrix_UB_13      0.0315929000
_diffrn_orient_matrix_UB_21      0.0406146000
_diffrn_orient_matrix_UB_22      -0.0559728000
_diffrn_orient_matrix_UB_23      0.0000576000
_diffrn_orient_matrix_UB_31      0.0419076000
_diffrn_orient_matrix_UB_32      0.0285520000
_diffrn_orient_matrix_UB_33      0.0298348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42107
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.886
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0524P)^2^+0.1988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                4576
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01206a2.cif
_cod_data_source_block           mx8972
_cod_depositor_comments
'Adding full bibliography for 7158250--7158251.cif.'
_cod_database_code               7158250
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C18(H18), C14(H14), C12(H12), C19(H19), C21(H21), C13(H13),
 C20(H20)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              78560
_shelx_hkl_checksum              13000
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.571