Synthesis of a phosphapyracene via metal-mediated cyclization: structural and reactivity effects of acenaphthene precursors.
Wang, Ge; Guino-O, Marites A; Glueck, David S.; Golen, James A.; Daley, Christopher J. A.; Rheingold, Arnold L.; Dalton transactions (Cambridge, England : 2003) 44 (2015) 9943–9954; doi:10.1039/c5dt00520e

data_7035058
_publ_section_title
;
 Synthesis of a phosphapyracene via metal-mediated cyclization: structural
 and reactivity effects of acenaphthene precursors.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9943
_journal_page_last               9954
_journal_paper_doi               10.1039/c5dt00520e
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C19 H18 B P'
_chemical_formula_sum            'C19 H18 B P'
_chemical_formula_weight         288.11
_chemical_name_systematic        GWr99
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.11.04 svn.r2830 for OlexSys, GUI svn.r4690)
;
_audit_update_record
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.000(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.795(3)
_cell_length_b                   6.3966(7)
_cell_length_c                   17.4407(17)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.143
_cell_measurement_theta_min      2.736
_cell_volume                     3100.4(6)
_computing_cell_refinement       'Bruker Saint'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.736
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0552 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9166.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0483P)^2^+1.8404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2897
_reflns_number_total             3852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt00520e2.cif
_cod_data_source_block           14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7035053--7035062.cif.
;
_cod_original_cell_volume        3100.3(5)
_cod_database_code               7035058
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.936
_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 B(H,H,H) groups
2. Restrained distances
 B1-H1C = B1-H1B = B1-H1A
 1.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13M) = Uanis(C13)
Uanis(C1M) = Uanis(C1)
Uanis(C2M) = Uanis(C2)
Uanis(C3M) = Uanis(C3)
Uanis(C4M) = Uanis(C4)
Uanis(C5M) = Uanis(C5)
Uanis(C6M) = Uanis(C6)
Uanis(C7M) = Uanis(C7)
Uanis(C8M) = Uanis(C8)
Uanis(C9M) = Uanis(C9)
Uanis(C10M) = Uanis(C10)
Uanis(C11M) = Uanis(C11)
Uanis(C12M) = Uanis(C12)
Uanis(B1M) = Uanis(B1)
Uanis(P1M) = Uanis(P1)
4. Same fragment restrains
{C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13}
as
{C1M, C2M, C3M, C4M, C5M, C6M, C7M, C8M, C9M, C10M, C11M, C12M, C13M}
5. Others
 Sof(P1M)=Sof(C1M)=Sof(C2M)=Sof(H2M)=Sof(C3M)=Sof(H3M)=Sof(C4M)=Sof(C5M)=
 Sof(H5MA)=Sof(H5MB)=Sof(C6M)=Sof(H6MA)=Sof(H6MB)=Sof(C7M)=Sof(C8M)=Sof(H8M)=
 Sof(C9M)=Sof(H9M)=Sof(C10M)=Sof(C11M)=Sof(C12M)=Sof(C13M)=Sof(H13C)=Sof(H13D)=
 Sof(B1M)=Sof(H1MA)=Sof(H1MB)=Sof(H1MC)=1-FVAR(1)
 Sof(P1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(C6)=Sof(H6B)=Sof(H6A)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(C11)=Sof(C12)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(B1)=Sof(H1A)=
 Sof(H1B)=Sof(H1C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6B,H6A), C13(H13A,H13B), C5M(H5MA,H5MB), C6M(H6MA,H6MB),
 C13M(H13C,H13D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C2M(H2M), C3M(H3M), C8M(H8M), C9M(H9M),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
6.c Idealised Me refined as rotating group:
 B1M(H1MA,H1MB,H1MC)
;
_shelx_res_checksum              35570