Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by different benzynes and allenes.
Yao, Liangliang; Fang, Bo; Hu, Qiong; Lei, Yu; Bao, Li; Hu, Yimin; Chemical communications (Cambridge, England) 56 (2020) 15185–15188; doi:10.1039/d0cc06300b

data_7127515
_publ_section_title
;
 Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by
 different benzynes and allenes.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15185
_journal_page_last               15188
_journal_paper_doi               10.1039/d0cc06300b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C47 H48 O6'
_chemical_formula_sum            'C47 H48 O6'
_chemical_formula_weight         708.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                108.997(2)
_cell_angle_beta                 95.076(3)
_cell_angle_gamma                94.172(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5959(5)
_cell_length_b                   18.7821(11)
_cell_length_c                   27.0537(15)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.335
_cell_measurement_theta_min      2.951
_cell_volume                     4089.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.3381
_diffrn_reflns_av_unetI/netI     0.1955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            84338
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.996
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1071 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.8836. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1028
_refine_ls_number_reflns         14383
_refine_ls_number_restraints     113
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.2677
_refine_ls_R_factor_gt           0.0949
_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^)+(0.0940P)^2^+1.7534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5142
_reflns_number_total             14383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06300b2.cif
_cod_data_source_block           4k
_cod_database_code               7127515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.983
_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. Restrained distances
 C3A-C2 = C2-C1A
 1.54 with sigma of 0.02
 C3A-C1A
 2.515 with sigma of 0.04
 C80-C83 \\sim C80-C83'
 with sigma of 0.02
 C83-C84 \\sim C83'-C84'
 with sigma of 0.02
 C2-C1 \\sim C2-C1A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2
 with sigma of 0.02
 C50-C49 \\sim C50A-C49
 with sigma of 0.02
 C49-C48A \\sim C49-C48
 with sigma of 0.02
3. Rigid bond restraints
 C83, C84
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C80, C83'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C2 \\sim C1 \\sim C1A \\sim C3 \\sim C3A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C83') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C84') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C50A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C49, C50, C48
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C1, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C1A, C3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C49, C50A, C48A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C83')=Sof(H83C)=Sof(H83D)=Sof(C84')=Sof(H84D)=Sof(H84E)=Sof(H84F)=1-FVAR(1)
 Sof(C83)=Sof(H83A)=Sof(H83B)=Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(H84C)=FVAR(1)
 Sof(H2B)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(H2A)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=FVAR(2)
 Sof(H49A)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=Sof(C48A)=Sof(H48D)=
 Sof(H48E)=Sof(H48F)=1-FVAR(3)
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(H49)=Sof(C50)=Sof(H50A)=Sof(H50B)=
 Sof(H50C)=FVAR(3)
7.a Riding coordinates:
 C84'(H84D,H84E,H84F), C3A(H3AA,H3AB,H3AC), C50A(H50D,H50E,H50F), C48A(H48D,
 H48E,H48F)
7.b Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B), C6(H6), C49(H49), C49(H49A), C53(H53)
7.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C25(H25A,H25B), C28(H28A,H28B), C36(H36A,
 H36B), C46(H46A,H46B), C57(H57A,H57B), C61(H61A,H61B), C72(H72A,H72B),
 C75(H75A,H75B), C83(H83A,H83B), C83'(H83C,H83D), C93(H93A,H93B)
7.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C26(H26), C31(H31), C32(H32),
 C34(H34), C35(H35), C41(H41), C42(H42), C44(H44), C45(H45), C63(H63), C64(H64),
  C65(H65), C66(H66), C73(H73), C78(H78), C79(H79), C81(H81), C82(H82),
 C88(H88), C89(H89), C91(H91), C92(H92)
7.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C29(H29A,
 H29B,H29C), C37(H37A,H37B,H37C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C),
 C50(H50A,H50B,H50C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C76(H76A,H76B,
 H76C), C84(H84A,H84B,H84C), C94(H94A,H94B,H94C), C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              76304
_olex2_submission_special_instructions 'No special instructions were received'