#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024466.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_4024466
loop_
_publ_author_name
'Jan Storch'
'Jan Sýkora'
'Jan Čermák'
'Jindřich Karban'
'Ivana Císařová'
'Aleš R°užička'
_publ_section_title
;
Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization
of Biphenylyl-Naphthalene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3090
_journal_page_last               3093
_journal_paper_doi               10.1021/jo900077j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C29 H22 O1'
_chemical_formula_sum            'C29 H22 O'
_chemical_formula_weight         386.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-09-22
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                87.141(2)
_cell_angle_beta                 79.041(2)
_cell_angle_gamma                66.122(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5863(3)
_cell_length_b                   8.6729(3)
_cell_length_c                   15.5859(7)
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     1041.48(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8347
_diffrn_reflns_theta_full        25.234
_diffrn_reflns_theta_max         27.133
_diffrn_reflns_theta_min         1.331
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9927
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1442
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000210
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.15 0.524 0.879 0.112 0.214 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0498
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0424
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3761
_reflns_number_total             4533
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.698(3)
_cod_data_source_file            jo900077j_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C29 H22 O1'
_cod_database_code               4024466
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O29 O 0.60797(11) 0.44833(11) 0.15803(6) 0.0332 1.0000 Uani . . . . . .
C1 C 0.08747(14) 0.67638(13) 0.24803(7) 0.0227 1.0000 Uani . . . . . .
C2 C 0.16076(16) 0.75705(14) 0.18549(7) 0.0273 1.0000 Uani . . . . . .
C3 C 0.06146(17) 0.87722(15) 0.13125(8) 0.0329 1.0000 Uani . . . . . .
C4 C -0.11148(17) 0.91529(15) 0.13991(8) 0.0337 1.0000 Uani . . . . . .
C5 C -0.37309(16) 0.87250(15) 0.21260(9) 0.0353 1.0000 Uani . . . . . .
C6 C -0.44973(16) 0.79225(17) 0.27217(9) 0.0376 1.0000 Uani . . . . . .
C7 C -0.35039(16) 0.66783(17) 0.32461(8) 0.0332 1.0000 Uani . . . . . .
C8 C -0.17687(15) 0.62893(14) 0.31756(7) 0.0274 1.0000 Uani . . . . . .
C9 C -0.09280(14) 0.71182(13) 0.25696(7) 0.0239 1.0000 Uani . . . . . .
C10 C -0.19299(15) 0.83390(13) 0.20250(7) 0.0278 1.0000 Uani . . . . . .
C11 C 0.19807(13) 0.55865(13) 0.30705(7) 0.0222 1.0000 Uani . . . . . .
C12 C 0.34173(14) 0.41092(13) 0.27399(7) 0.0235 1.0000 Uani . . . . . .
C13 C 0.45004(15) 0.30942(15) 0.32924(8) 0.0285 1.0000 Uani . . . . . .
C14 C 0.41924(16) 0.35334(16) 0.41696(8) 0.0335 1.0000 Uani . . . . . .
C15 C 0.27797(16) 0.49743(16) 0.45082(8) 0.0307 1.0000 Uani . . . . . .
C16 C 0.16525(14) 0.59986(14) 0.39725(7) 0.0247 1.0000 Uani . . . . . .
C17 C 0.01759(15) 0.74419(14) 0.43822(7) 0.0272 1.0000 Uani . . . . . .
C18 C -0.10433(15) 0.85398(15) 0.48047(8) 0.0300 1.0000 Uani . . . . . .
C19 C -0.25509(18) 0.98490(18) 0.53318(11) 0.0430 1.0000 Uani . . . . . .
C20 C 0.38431(13) 0.35343(13) 0.18020(7) 0.0236 1.0000 Uani . . . . . .
C21 C 0.52461(14) 0.36898(13) 0.12345(7) 0.0254 1.0000 Uani . . . . . .
C22 C 0.57125(16) 0.30715(14) 0.03728(8) 0.0295 1.0000 Uani . . . . . .
C23 C 0.47721(17) 0.22947(15) 0.00775(8) 0.0323 1.0000 Uani . . . . . .
C24 C 0.34010(16) 0.21069(14) 0.06254(8) 0.0307 1.0000 Uani . . . . . .
C25 C 0.29359(14) 0.27093(13) 0.14969(7) 0.0257 1.0000 Uani . . . . . .
C26 C 0.16127(15) 0.23873(14) 0.20903(8) 0.0276 1.0000 Uani . . . . . .
C27 C 0.05343(15) 0.20671(15) 0.25826(8) 0.0304 1.0000 Uani . . . . . .
C28 C -0.08262(19) 0.17462(19) 0.31705(10) 0.0390 1.0000 Uani . . . . . .
C30 C 0.77346(16) 0.43453(17) 0.11048(9) 0.0332 1.0000 Uani . . . . . .
H21 H 0.2878(18) 0.7302(17) 0.1799(9) 0.032(3) 1.0000 Uiso . . . . . .
H31 H 0.120(2) 0.934(2) 0.0875(11) 0.046(4) 1.0000 Uiso . . . . . .
H41 H -0.1817(19) 0.9984(19) 0.1047(10) 0.042(4) 1.0000 Uiso . . . . . .
H51 H -0.442(2) 0.960(2) 0.1739(11) 0.048(4) 1.0000 Uiso . . . . . .
H61 H -0.577(2) 0.816(2) 0.2788(11) 0.049(4) 1.0000 Uiso . . . . . .
H71 H -0.407(2) 0.6066(19) 0.3640(10) 0.042(4) 1.0000 Uiso . . . . . .
H81 H -0.1091(17) 0.5437(17) 0.3548(9) 0.027(3) 1.0000 Uiso . . . . . .
H131 H 0.5514(18) 0.2045(17) 0.3052(9) 0.032(3) 1.0000 Uiso . . . . . .
H141 H 0.497(2) 0.2818(19) 0.4550(10) 0.044(4) 1.0000 Uiso . . . . . .
H151 H 0.2531(19) 0.5298(18) 0.5134(10) 0.039(4) 1.0000 Uiso . . . . . .
H191 H -0.242(2) 1.091(3) 0.5344(13) 0.067(5) 1.0000 Uiso . . . . . .
H192 H -0.273(3) 0.947(3) 0.5939(17) 0.096(7) 1.0000 Uiso . . . . . .
H193 H -0.363(3) 1.008(3) 0.5089(14) 0.079(6) 1.0000 Uiso . . . . . .
H221 H 0.6687(19) 0.3192(18) -0.0026(10) 0.036(4) 1.0000 Uiso . . . . . .
H231 H 0.5125(19) 0.1848(19) -0.0547(10) 0.042(4) 1.0000 Uiso . . . . . .
H241 H 0.2754(18) 0.1552(17) 0.0420(9) 0.032(3) 1.0000 Uiso . . . . . .
H281 H -0.080(3) 0.067(3) 0.3087(13) 0.071(6) 1.0000 Uiso . . . . . .
H282 H -0.078(3) 0.187(3) 0.3792(15) 0.079(6) 1.0000 Uiso . . . . . .
H283 H -0.202(3) 0.263(3) 0.3099(14) 0.087(7) 1.0000 Uiso . . . . . .
H301 H 0.8180(19) 0.4913(19) 0.1483(10) 0.042(4) 1.0000 Uiso . . . . . .
H302 H 0.763(2) 0.490(2) 0.0530(11) 0.045(4) 1.0000 Uiso . . . . . .
H303 H 0.852(2) 0.315(2) 0.0987(10) 0.043(4) 1.0000 Uiso . . . . . .
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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 . O29 . C30 . 117.85(9) yes
C2 . C1 . C9 . 119.25(10) yes
C2 . C1 . C11 . 118.69(10) yes
C9 . C1 . C11 . 122.02(9) yes
C1 . C2 . C3 . 121.60(11) yes
C1 . C2 . H21 . 118.2(8) no
C3 . C2 . H21 . 120.2(8) no
C2 . C3 . C4 . 120.05(11) yes
C2 . C3 . H31 . 118.6(9) no
C4 . C3 . H31 . 121.4(9) no
C3 . C4 . C10 . 120.64(11) yes
C3 . C4 . H41 . 121.3(9) no
C10 . C4 . H41 . 118.0(9) no
C6 . C5 . C10 . 120.91(11) yes
C6 . C5 . H51 . 120.9(9) no
C10 . C5 . H51 . 118.1(9) no
C5 . C6 . C7 . 120.17(11) yes
C5 . C6 . H61 . 121.8(9) no
C7 . C6 . H61 . 117.9(9) no
C6 . C7 . C8 . 120.55(12) yes
C6 . C7 . H71 . 118.6(9) no
C8 . C7 . H71 . 120.8(9) no
C7 . C8 . C9 . 120.88(11) yes
C7 . C8 . H81 . 120.1(8) no
C9 . C8 . H81 . 119.0(8) no
C1 . C9 . C8 . 122.74(10) yes
C1 . C9 . C10 . 119.04(10) yes
C8 . C9 . C10 . 118.21(10) yes
C9 . C10 . C5 . 119.23(11) yes
C9 . C10 . C4 . 119.40(11) yes
C5 . C10 . C4 . 121.36(11) yes
C1 . C11 . C12 . 121.31(9) yes
C1 . C11 . C16 . 120.13(9) yes
C12 . C11 . C16 . 118.46(10) yes
C11 . C12 . C13 . 120.26(10) yes
C11 . C12 . C20 . 122.57(9) yes
C13 . C12 . C20 . 117.16(10) yes
C12 . C13 . C14 . 120.77(11) yes
C12 . C13 . H131 . 119.6(8) no
C14 . C13 . H131 . 119.6(8) no
C13 . C14 . C15 . 119.83(11) yes
C13 . C14 . H141 . 120.0(9) no
C15 . C14 . H141 . 120.1(9) no
C14 . C15 . C16 . 120.61(11) yes
C14 . C15 . H151 . 120.9(9) no
C16 . C15 . H151 . 118.5(9) no
C11 . C16 . C15 . 120.04(10) yes
C11 . C16 . C17 . 122.79(10) yes
C15 . C16 . C17 . 117.17(10) yes
C16 . C17 . C18 . 172.75(12) yes
C17 . C18 . C19 . 178.48(14) yes
C18 . C19 . H191 . 112.3(11) no
C18 . C19 . H192 . 109.7(13) no
H191 . C19 . H192 . 108.8(18) no
C18 . C19 . H193 . 110.6(12) no
H191 . C19 . H193 . 107.2(16) no
H192 . C19 . H193 . 108.1(18) no
C12 . C20 . C21 . 120.29(10) yes
C12 . C20 . C25 . 120.47(10) yes
C21 . C20 . C25 . 119.03(10) yes
C20 . C21 . O29 . 115.72(10) yes
C20 . C21 . C22 . 120.69(10) yes
O29 . C21 . C22 . 123.60(10) yes
C21 . C22 . C23 . 119.38(11) yes
C21 . C22 . H221 . 120.6(9) no
C23 . C22 . H221 . 120.0(8) no
C22 . C23 . C24 . 121.07(11) yes
C22 . C23 . H231 . 118.7(9) no
C24 . C23 . H231 . 120.2(9) no
C23 . C24 . C25 . 119.87(11) yes
C23 . C24 . H241 . 121.0(8) no
C25 . C24 . H241 . 119.1(8) no
C24 . C25 . C20 . 119.92(11) yes
C24 . C25 . C26 . 120.11(10) yes
C20 . C25 . C26 . 119.84(10) yes
C25 . C26 . C27 . 178.05(12) yes
C26 . C27 . C28 . 177.61(13) yes
C27 . C28 . H281 . 113.5(12) no
C27 . C28 . H282 . 112.1(12) no
H281 . C28 . H282 . 107.4(17) no
C27 . C28 . H283 . 110.3(12) no
H281 . C28 . H283 . 108.6(17) no
H282 . C28 . H283 . 104.5(16) no
O29 . C30 . H301 . 106.0(9) no
O29 . C30 . H302 . 111.1(9) no
H301 . C30 . H302 . 110.8(12) no
O29 . C30 . H303 . 110.1(9) no
H301 . C30 . H303 . 111.4(12) no
H302 . C30 . H303 . 107.6(13) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O29 . C21 . 1.3634(14) yes
O29 . C30 . 1.4330(14) yes
C1 . C2 . 1.3751(15) yes
C1 . C9 . 1.4307(15) yes
C1 . C11 . 1.4980(14) yes
C2 . C3 . 1.4124(16) yes
C2 . H21 . 1.006(14) no
C3 . C4 . 1.3651(19) yes
C3 . H31 . 1.000(16) no
C4 . C10 . 1.4183(18) yes
C4 . H41 . 0.959(15) no
C5 . C6 . 1.361(2) yes
C5 . C10 . 1.4219(17) yes
C5 . H51 . 1.010(16) no
C6 . C7 . 1.4114(19) yes
C6 . H61 . 1.009(16) no
C7 . C8 . 1.3713(16) yes
C7 . H71 . 0.978(16) no
C8 . C9 . 1.4224(16) yes
C8 . H81 . 0.979(13) no
C9 . C10 . 1.4254(15) yes
C11 . C12 . 1.4048(15) yes
C11 . C16 . 1.4148(15) yes
C12 . C13 . 1.3955(15) yes
C12 . C20 . 1.4971(15) yes
C13 . C14 . 1.3846(17) yes
C13 . H131 . 0.998(14) no
C14 . C15 . 1.3808(17) yes
C14 . H141 . 0.979(16) no
C15 . C16 . 1.4001(16) yes
C15 . H151 . 0.988(15) no
C16 . C17 . 1.4384(15) yes
C17 . C18 . 1.1957(16) yes
C18 . C19 . 1.4624(17) yes
C19 . H191 . 0.97(2) no
C19 . H192 . 0.99(3) no
C19 . H193 . 1.01(2) no
C20 . C21 . 1.4022(15) yes
C20 . C25 . 1.4039(15) yes
C21 . C22 . 1.3947(16) yes
C22 . C23 . 1.3894(18) yes
C22 . H221 . 0.982(15) no
C23 . C24 . 1.3787(18) yes
C23 . H231 . 1.010(16) no
C24 . C25 . 1.4047(16) yes
C24 . H241 . 0.971(14) no
C25 . C26 . 1.4338(16) yes
C26 . C27 . 1.2001(17) yes
C27 . C28 . 1.4534(18) yes
C28 . H281 . 0.94(2) no
C28 . H282 . 0.99(2) no
C28 . H283 . 1.02(2) no
C30 . H301 . 1.002(16) no
C30 . H302 . 0.998(17) no
C30 . H303 . 0.986(16) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24539737
