Regioselective Synthesis of Unsymmetric Tetra- and Pentasubstituted Pyrenes with a Strategy for Primary C-Alkylation at the 2-Position.
Dmytrejchuk, Ana M.; Jackson, Sydney N.; Meudom, Rolande; Gorden, John D.; Merner, Bradley L.; The Journal of organic chemistry 83 (2018) 10660–10667; doi:10.1021/acs.joc.8b01491

data_4035122
_publ_section_title
;
 Regioselective Synthesis of Unsymmetric Tetra- and Pentasubstituted
 Pyrenes with a Strategy for Primary C-Alkylation at the 2-Position.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10660
_journal_page_last               10667
_journal_paper_doi               10.1021/acs.joc.8b01491
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H16 F3 O5 S'
_chemical_formula_sum            'C21 H16 F3 O5 S'
_chemical_formula_weight         437.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                94.022(2)
_cell_angle_beta                 98.197(2)
_cell_angle_gamma                113.638(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7597(5)
_cell_length_b                   10.6780(6)
_cell_length_c                   11.1484(7)
_cell_measurement_reflns_used    9240
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.56
_cell_volume                     936.16(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      180.45
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45973
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1290 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5516
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             450.5720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.0993
_refine_diff_density_min         -1.1001
_refine_diff_density_rms         0.0981
_refine_ls_d_res_high            0.7801
_refine_ls_d_res_low             10.9252
_refine_ls_goodness_of_fit_ref   1.0486
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0486
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0819
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0963P)^2^+2.1310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3648
_reflns_number_total             4128
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b01491_si_002.cif
_cod_data_source_block           merner110714_0m
_cod_database_code               4035122
_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:
 C1(H1a,H1b), C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C15(H15), C11(H11), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'