Copper-Catalyzed Annulation: A Method for the Systematic Synthesis of Phenanthridinium Bromide.
Jhang, Yuan-Ye; Fan-Chiang, Tai-Ting; Huang, Jun-Min; Hsieh, Jen-Chieh; Organic letters 18 (2016) 1154–; doi:10.1021/acs.orglett.6b00269

data_1542501
_publ_section_title
;
 Copper-Catalyzed Annulation: A Method for the Systematic Synthesis of
 Phenanthridinium Bromide.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1154
_journal_paper_doi               10.1021/acs.orglett.6b00269
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C17 H20 Br N O'
_chemical_formula_weight         334.25
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4548(3)
_cell_length_b                   10.8630(5)
_cell_length_c                   19.6508(9)
_cell_measurement_reflns_used    2705
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.9868
_cell_measurement_theta_min      2.9224
_cell_volume                     1591.35(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13744
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         2.073
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0236P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2607
_reflns_number_total             3267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00269_si_001.cif
_cod_data_source_block           mo_150923LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542500--1542501.cif.
;
_cod_database_code               1542501
_shelxl_version_number           2014/6
_shelx_res_checksum              27939
_shelx_hkl_checksum              70534