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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/57/4125732.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_4125732
loop_
_publ_author_name
'González-Fernández, Elisa'
'Nicholls, Leo D. M.'
'Schaaf, Lukas D.'
'Farès, Christophe'
'Lehmann, Christian W.'
'Alcarazo, Manuel'
_publ_section_title
;
 Enantioselective Synthesis of [6]Carbohelicenes.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1428
_journal_page_last               1431
_journal_paper_doi               10.1021/jacs.6b12443
_journal_volume                  139
_journal_year                    2017
_chemical_compound_source        dichlormethane
_chemical_formula_moiety         'C28 H20'
_chemical_formula_sum            'C28 H20'
_chemical_formula_weight         356.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GON-GC-215
_audit_creation_date             2014-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6516(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4625(9)
_cell_length_b                   14.2040(7)
_cell_length_c                   7.6031(4)
_cell_measurement_reflns_used    4001
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.1083
_cell_measurement_theta_min      4.0090
_cell_volume                     1889.13(17)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20805
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.779
_diffrn_reflns_theta_min         4.009
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.95948
_exptl_absorpt_correction_T_min  0.91513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0406
_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/[σ²(Fo²)+(0.0655P)²+1.0045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1472
_reflns_number_total             1686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12443_si_006.cif
_cod_data_source_block           8788sadabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_Hall     '-c 2yc'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4125732
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.846
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.5000 0.58713(14) 0.7500 0.0205(4) Uani 1 2 d S T P
C2 C 0.5000 0.48619(14) 0.7500 0.0220(5) Uani 1 2 d S T P
C3 C 0.56602(8) 0.43504(11) 0.75248(19) 0.0242(4) Uani 1 1 d . . .
H3 H 0.5654 0.3682 0.7577 0.029 Uiso 1 1 calc R . .
C4 C 0.63029(8) 0.47970(10) 0.7475(2) 0.0243(4) Uani 1 1 d . . .
H4 H 0.6746 0.4445 0.7517 0.029 Uiso 1 1 calc R . .
C5 C 0.63089(8) 0.57897(10) 0.73613(18) 0.0222(4) Uani 1 1 d . . .
C6 C 0.56793(7) 0.63341(10) 0.73737(18) 0.0210(4) Uani 1 1 d . . .
C7 C 0.69849(8) 0.62091(10) 0.7135(2) 0.0238(4) Uani 1 1 d . . .
C8 C 0.75590(8) 0.65022(10) 0.6915(2) 0.0256(4) Uani 1 1 d . . .
C9 C 0.82401(9) 0.69124(12) 0.6643(2) 0.0322(4) Uani 1 1 d . . .
H9A H 0.8234 0.6793 0.5369 0.048 Uiso 1 1 calc GR . .
H9B H 0.8698 0.6627 0.7516 0.048 Uiso 1 1 calc GR . .
H9C H 0.8246 0.7593 0.6861 0.048 Uiso 1 1 calc GR . .
C10 C 0.57614(8) 0.73715(10) 0.71614(19) 0.0217(4) Uani 1 1 d . . .
C11 C 0.52950(8) 0.78600(10) 0.5622(2) 0.0229(4) Uani 1 1 d . . .
H11 H 0.4892 0.7538 0.4725 0.027 Uiso 1 1 calc R . .
C12 C 0.54120(8) 0.88094(11) 0.5386(2) 0.0278(4) Uani 1 1 d . . .
H12 H 0.5087 0.9135 0.4339 0.033 Uiso 1 1 calc R . .
C13 C 0.60027(9) 0.92857(11) 0.6678(2) 0.0308(4) Uani 1 1 d . . .
H13 H 0.6085 0.9935 0.6509 0.037 Uiso 1 1 calc R . .
C14 C 0.64725(8) 0.88125(10) 0.8214(2) 0.0282(4) Uani 1 1 d . . .
H14 H 0.6876 0.9137 0.9103 0.034 Uiso 1 1 calc R . .
C15 C 0.63523(8) 0.78644(10) 0.8447(2) 0.0243(4) Uani 1 1 d . . .
H15 H 0.6677 0.7543 0.9501 0.029 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0900
0.00 1.00 -1.00 0.0200
-2.00 -1.00 2.00 0.0800
-1.00 0.00 0.00 0.0700
1.00 0.00 0.00 0.0500
1.00 2.00 1.00 0.1100
1.00 -2.00 -1.00 0.0700
-3.00 -2.00 -1.00 0.0500
-1.00 -2.00 2.00 0.0800
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
C2 C1 C6 117.04(9) . .
C2 C1 C6 117.04(9) . 2_656
C6 C1 C6 125.92(18) . 2_656
C3 C2 C1 120.92(9) 2_656 .
C3 C2 C1 120.92(9) . .
C3 C2 C3 118.16(18) 2_656 .
C4 C3 C2 121.15(14) . .
C3 C4 C5 119.51(13) . .
C4 C5 C7 116.35(12) . .
C6 C5 C4 121.89(13) . .
C6 C5 C7 121.69(13) . .
C1 C6 C10 125.11(13) . .
C5 C6 C1 119.30(13) . .
C5 C6 C10 115.52(12) . .
C8 C7 C5 175.81(15) . .
C7 C8 C9 176.77(15) . .
C11 C10 C6 121.58(12) . .
C11 C10 C15 118.15(13) . .
C15 C10 C6 120.09(12) . .
C12 C11 C10 120.80(13) . .
C11 C12 C13 120.16(14) . .
C14 C13 C12 119.89(14) . .
C13 C14 C15 119.79(14) . .
C14 C15 C10 121.21(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.434(3) .
C1 C6 1.4461(16) 2_656
C1 C6 1.4461(16) .
C2 C3 1.4139(17) .
C2 C3 1.4138(17) 2_656
C3 C4 1.357(2) .
C4 C5 1.413(2) .
C5 C6 1.3988(19) .
C5 C7 1.4419(19) .
C6 C10 1.495(2) .
C7 C8 1.199(2) .
C8 C9 1.460(2) .
C10 C11 1.396(2) .
C10 C15 1.398(2) .
C11 C12 1.386(2) .
C12 C13 1.388(2) .
C13 C14 1.386(2) .
C14 C15 1.385(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125144
