Generation of a series of B<sub>n</sub> fused oligo-naphthalenes (n = 1 to 3) from a B<sub>1</sub>-polycyclic aromatic hydrocarbon.
Kahan, R. J.; Crossley, D. L.; Cid, J.; Radcliffe, J. E.; Woodward, A. W.; Fasano, V.; Endres, S.; Whitehead, G. F. S.; Ingleson, M. J.; Chemical communications (Cambridge, England) 54 (2018) 9490–9493; doi:10.1039/c8cc04701d

data_7122119
_publ_section_title
;
 Generation of a series of B<sub>n</sub> fused oligo-naphthalenes (n = 1
 to 3) from a B<sub>1</sub>-polycyclic aromatic hydrocarbon.
;
_journal_issue                   68
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9490
_journal_page_last               9493
_journal_paper_doi               10.1039/c8cc04701d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C39 H30.89 B Br0.11'
_chemical_formula_sum            'C39 H30.89 B Br0.11'
_chemical_formula_weight         518.93
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-08 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4564(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.71416(15)
_cell_length_b                   18.5823(3)
_cell_length_c                   14.07156(18)
_cell_measurement_reflns_used    24943
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.6090
_cell_measurement_theta_min      2.3590
_cell_volume                     2788.87(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.7b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.7b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.7b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     46.00  94.00   1.00    1.00    --    5.00  57.00  90.00   48
  2  \w     -9.00  18.00   1.00    1.00    --    5.00  57.00  90.00   27
  3  \w    -55.00  -6.00   1.00    1.00    --  -45.10 -76.00-120.00   49
  4  \w   -129.00 -82.00   1.00    1.00    --  -45.10 -50.00  56.56   47
  5  \w    -34.00  32.00   1.00    1.00    --  -45.10  64.00  -8.07   66
  6  \w    -53.00  43.00   1.00    1.00    --  -45.10  57.00 -30.00   96
  7  \w   -124.00 -82.00   1.00    1.00    --  -45.10 -76.00-120.00   42
  8  \w    -74.00   9.00   1.00    1.00    --  -45.10  61.00 173.36   83
  9  \w    -80.00 -54.00   1.00    1.00    --  -45.10  64.00  -8.07   26
 10  \w    -78.00  44.00   1.00    1.00    --  -45.10  57.00  90.00  122
 11  \w   -198.00 -79.00   1.00    1.00    -- -110.00 -57.00-150.00  119
 12  \w   -146.00-120.00   1.00    1.00    -- -110.00  38.00-150.00   26
 13  \w   -139.00-113.00   1.00    1.00    -- -110.00  76.00  30.00   26
 14  \w    -92.00 -62.00   1.00    1.00    -- -110.00  76.00  30.00   30
 15  \w   -138.00 -61.00   1.00    1.00    -- -110.00  76.00 120.00   77
 16  \w   -121.00 -22.00   1.00    1.00    -- -110.00  76.00 -60.00   99
 17  \w   -198.00 -75.00   1.00    1.00    -- -110.00 -64.00 -62.85  123
 18  \w   -138.00-112.00   1.00    1.00    -- -110.00  38.00  90.00   26
 19  \w   -143.00 -73.00   1.00    1.00    -- -110.00  76.00   0.00   70
 20  \w   -199.00 -72.00   1.00    1.00    -- -110.00 -76.00-120.00  127
 21  \w   -111.00 -70.00   1.00    1.00    -- -110.00 -75.00 -52.09   41
 22  \w   -106.00 -81.00   1.00    1.00    -- -110.00  38.00  90.00   25
 23  \w    -84.00 -22.00   1.00    1.00    -- -110.00  76.00-150.00   62
 24  \w    -91.00 -66.00   1.00    1.00    -- -110.00  38.00  60.00   25
 25  \w   -149.00 -61.00   1.00    1.00    -- -110.00  76.00  60.00   88
 26  \w   -119.00 -94.00   1.00    1.00    -- -110.00  57.00 -90.00   25
 27  \w    -98.00 -73.00   1.00    1.00    -- -110.00 -76.00 -60.00   25
 28  \w   -100.00 -70.00   1.00    1.00    -- -110.00 -76.00 -30.00   30
 29  \w   -157.00-131.00   1.00    1.00    -- -110.00 -57.00-180.00   26
 30  \w   -121.00 -78.00   1.00    1.00    -- -110.00 -57.00-180.00   43
 31  \w   -121.00 -95.00   1.00    1.00    -- -110.00  19.00-180.00   26
 32  \w   -192.00-133.00   1.00    1.00    -- -110.00  19.00-180.00   59
 33  \w   -199.00 -70.00   1.00    1.00    -- -110.00 -76.00 -34.89  129
 34  \w   -171.00 -75.00   1.00    1.00    -- -110.00 -76.00 150.00   96
 35  \w    -95.00 -70.00   1.00    1.00    -- -110.00 -75.00 -19.81   25
 36  \w   -177.00-144.00   1.00    1.00    -- -110.00 -75.00 -19.81   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0525375000
_diffrn_orient_matrix_UB_12      0.0568365000
_diffrn_orient_matrix_UB_13      0.0652914000
_diffrn_orient_matrix_UB_21      -0.0977576000
_diffrn_orient_matrix_UB_22      -0.0547660000
_diffrn_orient_matrix_UB_23      0.0285870000
_diffrn_orient_matrix_UB_31      0.0924963000
_diffrn_orient_matrix_UB_32      -0.0254412000
_diffrn_orient_matrix_UB_33      0.0836924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36142
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.410
_diffrn_reflns_theta_min         3.952
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.7b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             1095
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         5791
_refine_ls_number_restraints     1241
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0410P)^2^+1.7964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5487
_reflns_number_total             5791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04701d2.cif
_cod_data_source_block           rmji7
_cod_depositor_comments
'Adding full bibliography for 7122119--7122120.cif.'
_cod_database_code               7122119
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.795
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
 Br3-C3_1 = Br1-C3_2
 1.9 with sigma of 0.01
 C2_1-Br3 \\sim Br3-C4_1
 with sigma of 0.02
 C6_1-B1 \\sim B1-C2_1
 with sigma of 0.02
 C1_1-B1 \\sim C1_3-B1 \\sim C1_2-B1
 with sigma of 0.001
3. Restrained planarity
 C1_2, C2_2, C3_2, C4_2, C5_2, C7_2, Br1, C8_2, C6_2, C9_2
 with sigma of 0.1
 Br3, C2_1, C3_1, C4_1, C5_1, C6_1, C8_1, C9_1, C1_1, C7_1
 with sigma of 0.1
 C6_1, C1_1, C2_1, B1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C34 \\sim C39 \\sim C35 \\sim C36 \\sim C38 \\sim C37 \\sim C35A \\sim C37A
\\sim C36A \\sim C38A \\sim C39A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C7_2 \\sim C2_3: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
Br1 \\sim C5_1 \\sim C8_1 \\sim C8_2 \\sim C3_3 \\sim C8_3 \\sim C4_1 \\sim
C6_1 \\sim C9_1 \\sim C2_2 \\sim C3_2 \\sim C4_2 \\sim C7_2 \\sim C2_3 \\sim
C4_3 \\sim C7_3 \\sim Br3 \\sim C1_1 \\sim C2_1 \\sim C3_1 \\sim C7_1 \\sim
C1_2 \\sim C5_2 \\sim C6_2 \\sim C9_2 \\sim C1_3 \\sim C5_3 \\sim C6_3 \\sim
C9_3: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Rigid body (RIGU) restrains
 C39, C39A, C38, C38A, C37, C37A, C36, C36A, C35A, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Br1, C5_1, C8_1, C8_2, C3_3, C8_3, C4_1, C6_1, C9_1, C2_2, C3_2, C4_2, C7_2,
 C2_3, C4_3, C7_3, Br3, C1_1, C2_1, C3_1, C7_1, C1_2, C5_2, C6_2, C9_2, C1_3,
 C5_3, C6_3, C9_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3}
{C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1}
as
{C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2} sigma for 1-2: 0.01 1-3:
0.02
7. Others
 1*[Sof(Br3)+Sof(C1)+Sof(C2)+Sof(C3)+Sof(C4)+Sof(C5)+Sof(H5)+Sof(C6)+Sof(C7)+
 Sof(H7A)+Sof(H7B)+Sof(H7C)+Sof(C8)+Sof(H8A)+Sof(H8B)+Sof(H8C)+Sof(C9)+Sof(H9A)+
 Sof(H9B)+Sof(H9C)]+1*[Sof(Br1)+Sof(C1)+Sof(C2)+Sof(C3)+Sof(C4)+Sof(C5)+Sof(H5)+
 Sof(C6)+Sof(C7)+Sof(H7A)+Sof(H7B)+Sof(H7C)+Sof(C8)+Sof(H8A)+Sof(H8B)+Sof(H8C)+
 Sof(C9)+Sof(H9A)+Sof(H9B)+Sof(H9C)]+1*[Sof(C1)+Sof(C2)+Sof(C3)+Sof(H3)+Sof(C4)+
 Sof(C5)+Sof(H5)+Sof(C6)+Sof(C7)+Sof(H7A)+Sof(H7B)+Sof(H7C)+Sof(C8)+Sof(H8A)+
 Sof(H8B)+Sof(H8C)+Sof(C9)+Sof(H9A)+Sof(H9B)+Sof(H9C)]=1 with esd of 0.00001
 Sof(Br3)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H9C)=FVAR(1)
 Sof(Br1)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H9C)=FVAR(2)
 Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H9C)=FVAR(3)
 Sof(C39)=Sof(H39)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C38)=Sof(H38)=
 Sof(C37)=Sof(H37)=1-FVAR(4)
 Sof(C35A)=Sof(H35A)=Sof(C37A)=Sof(H37A)=Sof(C36A)=Sof(H36A)=Sof(C38A)=
 Sof(H38A)=Sof(C39A)=Sof(H39A)=FVAR(4)
8.a Riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
8.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B)
8.c Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
8.d Aromatic/amide H refined with riding coordinates:
 C28(H28), C11(H11), C17(H17), C13(H13), C22(H22), C12(H12), C15(H15),
 C16(H16), C25(H25), C23(H23), C24(H24), C39(H39), C35(H35), C36(H36), C38(H38),
  C37(H37), C35A(H35A), C37A(H37A), C36A(H36A), C38A(H38A), C39A(H39A), C5(H5),
 C3(H3), C5(H5), C5(H5)
8.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              92605
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.773