#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:23:23 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038057.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038057
loop_
_publ_author_name
'Hoenig, Samuel M.'
'Yan, Youmian'
'Dougherty, Emily A.'
'Hudson, Reuben'
'Petovic, Sava'
'Lee, Christopher K.'
'Hu, Yusheng'
'Gomez, Lucas S.'
'Katz, Jeffrey L.'
_publ_section_title
;
 Convergent Strategy for the Synthesis of Oxa-, Thia-, and
 Selena[5]helicenes by Acetylene-Activated SNAr Reactions.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4553
_journal_page_last               4559
_journal_paper_doi               10.1021/acs.joc.0c00052
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C26 H15 F S'
_chemical_formula_sum            'C26 H15 F S'
_chemical_formula_weight         378.47
_chemical_name_systematic
5-fluoro-2-phenylbenzo[5,6]phenanthro[4,3-b]thiophene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-03
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.048(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8863(5)
_cell_length_b                   18.6245(7)
_cell_length_c                   7.6360(3)
_cell_measurement_reflns_used    9731
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      2.69
_cell_measurement_theta_min      27.05
_cell_volume                     1818.80(12)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      173.03
_diffrn.ambient_temp_esd         2.0
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker Photon 50'
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker Photon 50'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26983
_diffrn_reflns_theta_full        27.0755
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens KFFMO2K--90C'
_diffrn_standards_number         0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784.8399
_exptl_crystal_recrystallization_method
'vapor diffusion from chloroform-hexanes'
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2330
_refine_diff_density_min         -0.3075
_refine_diff_density_rms         0.0530
_refine_ls_d_res_high            0.7807
_refine_ls_d_res_low             7.0195
_refine_ls_goodness_of_fit_ref   0.9850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9850
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.0539
_refine_ls_shift/su_mean         0.0108
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²+0.3008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                3485
_reflns_number_total             3987
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo0c00052_si_003.cif
_cod_data_source_block           JLKIII49_2_0ma_a
_cod_depositor_comments
'Adding full bibliography for 4038056--4038057.cif.'
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4038057
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
;
_olex2_exptl_crystal_mounting_method 'paratone oil on a 500 micron loop'
_olex2_submission_original_sample_id JLKIII49_2_0ma_a
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
S001 S 0.30058(3) 0.600647(18) 0.58819(5) 0.02973(14) Uani 1.000000 .
F002 F -0.11474(8) 0.72524(6) 0.45376(14) 0.0457(3) Uani 1.000000 .
C003 C 0.09091(12) 0.53756(7) 0.76109(17) 0.0289(3) Uani 1.000000 .
C004 C 0.08763(12) 0.60233(7) 0.65531(17) 0.0269(3) Uani 1.000000 .
C005 C 0.17478(11) 0.63491(7) 0.58707(17) 0.0262(3) Uani 1.000000 .
C006 C 0.16399(12) 0.69745(7) 0.48256(17) 0.0288(3) Uani 1.000000 .
C007 C 0.33720(12) 0.66930(7) 0.45309(17) 0.0284(3) Uani 1.000000 .
C008 C -0.01242(12) 0.63193(8) 0.59549(18) 0.0305(3) Uani 1.000000 .
C009 C 0.44336(12) 0.67121(8) 0.40400(18) 0.0311(3) Uani 1.000000 .
C00A C 0.18279(13) 0.51344(8) 0.87479(18) 0.0318(3) Uani 1.000000 .
C00B C 0.25731(13) 0.71657(7) 0.41168(18) 0.0307(3) Uani 1.000000 .
H00B H 0.26330(13) 0.75832(7) 0.34213(18) 0.0369(4) Uiso 1.000000 R
C00C C 0.06527(13) 0.73128(8) 0.44640(19) 0.0327(3) Uani 1.000000 .
H00C H 0.05777(13) 0.77610(8) 0.38677(19) 0.0393(4) Uiso 1.000000 R
C00D C -0.01745(13) 0.69737(8) 0.49996(19) 0.0335(3) Uani 1.000000 .
C00E C -0.00108(14) 0.49650(8) 0.75520(18) 0.0332(3) Uani 1.000000 .
C00F C 0.26295(14) 0.55998(9) 0.94773(19) 0.0364(4) Uani 1.000000 .
H00F H 0.25744(14) 0.60988(9) 0.92238(19) 0.0437(4) Uiso 1.000000 R
C00G C 0.18645(15) 0.44076(8) 0.93412(19) 0.0380(4) Uani 1.000000 .
C00H C 0.09524(18) 0.39688(8) 0.8987(2) 0.0440(4) Uani 1.000000 .
H00H H 0.09895(18) 0.34733(8) 0.9284(2) 0.0527(5) Uiso 1.000000 R
C00I C -0.09874(14) 0.52598(9) 0.6839(2) 0.0383(4) Uani 1.000000 .
H00I H -0.16037(14) 0.49790(9) 0.6825(2) 0.0459(4) Uiso 1.000000 R
C00J C -0.10545(13) 0.59346(9) 0.6179(2) 0.0366(3) Uani 1.000000 .
H00J H -0.17190(13) 0.61509(9) 0.5866(2) 0.0439(4) Uiso 1.000000 R
C00K C 0.00425(16) 0.42491(9) 0.8239(2) 0.0403(4) Uani 1.000000 .
H00K H -0.05755(16) 0.39670(9) 0.8165(2) 0.0483(5) Uiso 1.000000 R
C00L C 0.51087(14) 0.61251(9) 0.4345(2) 0.0398(4) Uani 1.000000 .
H00L H 0.48756(14) 0.57039(9) 0.4879(2) 0.0478(4) Uiso 1.000000 R
C00M C 0.48058(14) 0.73220(9) 0.3241(2) 0.0393(4) Uani 1.000000 .
H00M H 0.43637(14) 0.77285(9) 0.3022(2) 0.0471(4) Uiso 1.000000 R
C00N C 0.58049(15) 0.73406(11) 0.2769(2) 0.0453(4) Uani 1.000000 .
H00N H 0.60403(15) 0.77574(11) 0.2219(2) 0.0543(5) Uiso 1.000000 R
C00O C 0.64676(15) 0.67580(12) 0.3089(2) 0.0483(4) Uani 1.000000 .
H00O H 0.71573(15) 0.67747(12) 0.2771(2) 0.0579(5) Uiso 1.000000 R
C00P C 0.27666(19) 0.41599(10) 1.0396(2) 0.0500(5) Uani 1.000000 .
H00P H 0.28168(19) 0.36675(10) 1.0721(2) 0.0600(6) Uiso 1.000000 R
C00Q C 0.34904(16) 0.53485(11) 1.0548(2) 0.0466(4) Uani 1.000000 .
H00Q H 0.40285(16) 0.56703(11) 1.1005(2) 0.0559(5) Uiso 1.000000 R
C00R C 0.61145(15) 0.61507(11) 0.3876(3) 0.0493(4) Uani 1.000000 .
H00R H 0.65644(15) 0.57482(11) 0.4098(3) 0.0592(5) Uiso 1.000000 R
C00S C 0.35693(18) 0.46131(12) 1.0962(2) 0.0539(5) Uani 1.000000 .
H00S H 0.41822(18) 0.44321(12) 1.1636(2) 0.0647(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 S001 C005 92.74(7) . . ?
C00A C003 C004 123.84(13) . . ?
C00E C003 C004 117.89(14) . . ?
C00E C003 C00A 118.26(13) . . ?
C005 C004 C003 125.86(13) . . ?
C008 C004 C003 117.65(14) . . ?
C008 C004 C005 116.05(12) . . ?
C004 C005 S001 127.96(10) . . ?
C006 C005 S001 109.43(11) . . ?
C006 C005 C004 122.00(13) . . ?
C00B C006 C005 113.15(13) . . ?
C00C C006 C005 120.14(14) . . ?
C00C C006 C00B 126.52(13) . . ?
C009 C007 S001 119.93(11) . . ?
C00B C007 S001 111.08(12) . . ?
C00B C007 C009 128.97(13) . . ?
C00D C008 C004 118.69(14) . . ?
C00J C008 C004 120.56(14) . . ?
C00J C008 C00D 120.53(14) . . ?
C00L C009 C007 121.38(14) . . ?
C00M C009 C007 120.80(14) . . ?
C00M C009 C00L 117.82(16) . . ?
C00F C00A C003 123.41(13) . . ?
C00G C00A C003 118.46(15) . . ?
C00G C00A C00F 117.64(15) . . ?
C007 C00B C006 113.56(13) . . ?
H00B C00B C006 123.22(8) . . ?
H00B C00B C007 123.22(9) . . ?
H00C C00C C006 121.37(9) . . ?
C00D C00C C006 117.27(13) . . ?
C00D C00C H00C 121.37(9) . . ?
C008 C00D F002 116.30(15) . . ?
C00C C00D F002 118.73(14) . . ?
C00C C00D C008 124.91(14) . . ?
C00I C00E C003 120.40(14) . . ?
C00K C00E C003 119.49(16) . . ?
C00K C00E C00I 120.10(16) . . ?
H00F C00F C00A 119.22(9) . . ?
C00Q C00F C00A 121.57(16) . . ?
C00Q C00F H00F 119.22(11) . . ?
C00H C00G C00A 119.21(16) . . ?
C00P C00G C00A 119.04(17) . . ?
C00P C00G C00H 121.50(16) . . ?
H00H C00H C00G 119.61(10) . . ?
C00K C00H C00G 120.79(14) . . ?
C00K C00H H00H 119.61(10) . . ?
H00I C00I C00E 119.48(9) . . ?
C00J C00I C00E 121.04(15) . . ?
C00J C00I H00I 119.48(10) . . ?
C00I C00J C008 119.71(16) . . ?
H00J C00J C008 120.15(9) . . ?
H00J C00J C00I 120.15(10) . . ?
C00H C00K C00E 121.16(16) . . ?
H00K C00K C00E 119.42(11) . . ?
H00K C00K C00H 119.42(10) . . ?
H00L C00L C009 119.60(10) . . ?
C00R C00L C009 120.80(17) . . ?
C00R C00L H00L 119.60(11) . . ?
H00M C00M C009 119.52(10) . . ?
C00N C00M C009 120.96(16) . . ?
C00N C00M H00M 119.52(11) . . ?
H00N C00N C00M 119.68(11) . . ?
C00O C00N C00M 120.64(17) . . ?
C00O C00N H00N 119.68(12) . . ?
H00O C00O C00N 120.37(12) . . ?
C00R C00O C00N 119.27(18) . . ?
C00R C00O H00O 120.37(12) . . ?
H00P C00P C00G 119.36(11) . . ?
C00S C00P C00G 121.27(17) . . ?
C00S C00P H00P 119.36(11) . . ?
H00Q C00Q C00F 120.16(11) . . ?
C00S C00Q C00F 119.68(19) . . ?
C00S C00Q H00Q 120.16(12) . . ?
C00O C00R C00L 120.50(18) . . ?
H00R C00R C00L 119.75(11) . . ?
H00R C00R C00O 119.75(12) . . ?
C00Q C00S C00P 120.04(18) . . ?
H00S C00S C00P 119.98(11) . . ?
H00S C00S C00Q 119.98(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C005 1.7413(15) . ?
S001 C007 1.7440(14) . ?
F002 C00D 1.3628(17) . ?
C003 C004 1.4495(18) . ?
C003 C00A 1.451(2) . ?
C003 C00E 1.407(2) . ?
C004 C005 1.430(2) . ?
C004 C008 1.425(2) . ?
C005 C006 1.4091(18) . ?
C006 C00B 1.423(2) . ?
C006 C00C 1.416(2) . ?
C007 C009 1.463(2) . ?
C007 C00B 1.362(2) . ?
C008 C00D 1.418(2) . ?
C008 C00J 1.425(2) . ?
C009 C00L 1.399(2) . ?
C009 C00M 1.401(2) . ?
C00A C00F 1.410(2) . ?
C00A C00G 1.426(2) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00C C00D 1.345(2) . ?
C00E C00I 1.419(2) . ?
C00E C00K 1.431(2) . ?
C00F H00F 0.9500 . ?
C00F C00Q 1.377(2) . ?
C00G C00H 1.430(3) . ?
C00G C00P 1.408(3) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.345(3) . ?
C00I H00I 0.9500 . ?
C00I C00J 1.353(2) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00R 1.387(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.379(3) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.384(3) . ?
C00O H00O 0.9500 . ?
C00O C00R 1.384(3) . ?
C00P H00P 0.9500 . ?
C00P C00S 1.364(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C00S 1.406(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
