One-pot syntheses of irida-polycyclic aromatic hydrocarbons
Hu, Yuxuan; Zhang, Jing; Wang, Xiaoyan; Lu, Zhengyu; Zhang, Fangfang; Yang, Xiaofei; Ma, Zhihua; Yin, Jun; Xia, Haiping; Liu, Shenghua; Chemical Science  (2019) –; doi:10.1039/C9SC03914G

data_1552419
_publ_section_title
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 One-pot syntheses of irida-polycyclic aromatic hydrocarbons
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03914G
_journal_year                    2019
_chemical_formula_moiety         'C37 H40 Cl Ir O P, F6 P'
_chemical_formula_sum            'C37 H40 Cl F6 Ir O P2'
_chemical_formula_weight         904.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-14 deposited with the CCDC.    2019-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.480(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8879(8)
_cell_length_b                   37.424(3)
_cell_length_c                   10.5294(8)
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.418
_cell_measurement_theta_min      4.375
_cell_volume                     3491.6(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1849
_diffrn_reflns_av_unetI/netI     0.1862
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12613
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        63.989
_diffrn_reflns_theta_max         63.989
_diffrn_reflns_theta_min         4.374
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.514
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1316 before and 0.0674 after correction. The Ratio of minimum to maximum transmission is 0.5966. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       plate
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         3.272
_refine_diff_density_min         -4.817
_refine_diff_density_rms         0.360
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1817
_refine_ls_R_factor_gt           0.1047
_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^)+(0.1691P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2362
_refine_ls_wR_factor_ref         0.2856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3292
_reflns_number_total             5518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03914g2.cif
_cod_data_source_block           Complex_8a
_cod_database_code               1552419
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.648
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C27) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C32) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C32) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C28) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C17) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C27) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C25) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C36) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21)
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              89221
_olex2_submission_special_instructions 'No special instructions were received'