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_7158251
_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_formula_moiety         'C19 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-30 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                   10.72690(10)
_cell_length_b                   10.72690(10)
_cell_length_c                   14.5422(3)
_cell_measurement_reflns_used    24486
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.0460
_cell_measurement_theta_min      1.8560
_cell_volume                     1673.32(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_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    0.80    --    5.00  45.00 120.00  356
  2  \w   -104.00  74.00   0.50    0.80    --  -14.80  45.00 120.00  356
  3  \w   -104.00  74.00   0.50    0.80    --  -14.80  45.00  -6.10  356
  4  \w   -104.00  74.00   0.50    0.80    --  -14.80  45.00 173.74  356
  5  \w   -104.00  74.00   0.50    0.80    --  -14.80  45.00  60.00  356
  6  \w    -84.00 -23.00   0.50    0.80    --    5.00  45.00  90.00  122
;
_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      0.0207199000
_diffrn_orient_matrix_UB_12      -0.0352564000
_diffrn_orient_matrix_UB_13      0.0383438000
_diffrn_orient_matrix_UB_21      0.0422691000
_diffrn_orient_matrix_UB_22      -0.0326731000
_diffrn_orient_matrix_UB_23      -0.0287578000
_diffrn_orient_matrix_UB_31      0.0464994000
_diffrn_orient_matrix_UB_32      0.0453147000
_diffrn_orient_matrix_UB_33      0.0091155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.761
_diffrn_reflns_theta_min         1.898
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47037
_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    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4706
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0293P)^2^+0.3079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0574
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                4343
_reflns_number_total             4706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01206a2.cif
_cod_data_source_block           mx8755
_cod_depositor_comments
'Adding full bibliography for 7158250--7158251.cif.'
_cod_original_cell_volume        1673.32(5)
_cod_database_code               7158251
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONBr
_shelx_estimated_absorpt_t_max   0.478
_shelx_estimated_absorpt_t_min   0.365
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C6(H6), C17(H17), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              76633
_shelx_hkl_checksum              91488
_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 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.565