#------------------------------------------------------------------------------
#$Date: 2022-04-28 00:55:24 +0300 (Thu, 28 Apr 2022) $
#$Revision: 274720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/00/7130026.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_7130026
loop_
_publ_author_name
'Silber, Vincent'
'Kyritsakas, Nathalie'
'Jean, Marion'
'Vanthuyne, Nicolas'
'Ruppert, Romain'
_publ_section_title
;
 Synthesis of a helicene-fused porphyrin leading to a π-extended chiral
 chromophore
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01475K
_journal_year                    2022
_chemical_formula_moiety         'C28 H18 O2'
_chemical_formula_sum            'C28 H18 O2'
_chemical_formula_weight         386.42
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-07 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.2170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5972(4)
_cell_length_b                   12.8994(5)
_cell_length_c                   13.7902(5)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.49
_cell_volume                     1881.43(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            71287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_min         2.262
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0375
_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)+(0.0503P)²+0.7407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3925
_reflns_number_total             4496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01475k2.cif
_cod_data_source_block           ejwvs211201
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130026
_shelx_shelxl_version_number     2018/3
_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_min   0.983
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60630(7) 0.30448(6) 0.38159(6) 0.02070(17) Uani 1 1 d . . . . .
O2 O 0.12585(9) 0.59728(8) 0.11795(9) 0.0409(2) Uani 1 1 d . . . . .
C22 C 0.67987(9) 0.49843(8) 0.21904(8) 0.0197(2) Uani 1 1 d . . . . .
H22 H 0.648011 0.552428 0.248014 0.024 Uiso 1 1 calc R U . . .
C2 C 0.50921(9) 0.35725(8) 0.30826(8) 0.0187(2) Uani 1 1 d . . . . .
C23 C 0.75829(9) 0.42159(8) 0.28766(8) 0.0190(2) Uani 1 1 d . . . . .
C24 C 0.79830(10) 0.42429(8) 0.40219(8) 0.0203(2) Uani 1 1 d . . . . .
C26 C 0.60815(10) 0.52036(8) 0.41032(8) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.50469(10) 0.46603(8) 0.32738(8) 0.0197(2) Uani 1 1 d . . . . .
C6 C 0.38884(10) 0.51856(8) 0.26935(9) 0.0219(2) Uani 1 1 d . . . . .
C3 C 0.41466(10) 0.30895(9) 0.22296(9) 0.0220(2) Uani 1 1 d . . . . .
H3 H 0.422157 0.237966 0.208104 0.026 Uiso 1 1 calc R U . . .
C25 C 0.73918(10) 0.48716(8) 0.45556(8) 0.0213(2) Uani 1 1 d . . . . .
C21 C 0.64849(10) 0.49704(9) 0.11136(9) 0.0243(2) Uani 1 1 d . . . . .
H21 H 0.596527 0.550218 0.067296 0.029 Uiso 1 1 calc R U . . .
C9 C 0.57768(11) 0.61141(9) 0.45193(9) 0.0255(2) Uani 1 1 d . . . . .
C5 C 0.29116(10) 0.46733(9) 0.18189(9) 0.0238(2) Uani 1 1 d . . . . .
C18 C 0.81112(10) 0.34629(8) 0.24226(9) 0.0238(2) Uani 1 1 d . . . . .
C27 C 0.62945(11) 0.20020(8) 0.35806(9) 0.0240(2) Uani 1 1 d . . . . .
H27A H 0.559652 0.155533 0.354934 0.036 Uiso 1 1 calc R U . . .
H27B H 0.708730 0.175205 0.413807 0.036 Uiso 1 1 calc R U . . .
H27C H 0.635780 0.198615 0.289358 0.036 Uiso 1 1 calc R U . . .
C12 C 0.81589(11) 0.52013(9) 0.56074(9) 0.0272(2) Uani 1 1 d . . . . .
C4 C 0.30858(10) 0.36565(9) 0.15932(9) 0.0242(2) Uani 1 1 d . . . . .
H4 H 0.246137 0.333500 0.098431 0.029 Uiso 1 1 calc R U . . .
C7 C 0.37058(11) 0.61961(9) 0.30445(10) 0.0286(3) Uani 1 1 d . . . . .
H7 H 0.296860 0.658376 0.263732 0.034 Uiso 1 1 calc R U . . .
C15 C 0.90847(10) 0.36862(9) 0.46454(9) 0.0260(2) Uani 1 1 d . . . . .
C20 C 0.69300(12) 0.41732(10) 0.06642(9) 0.0290(3) Uani 1 1 d . . . . .
H20 H 0.667450 0.414232 -0.008378 0.035 Uiso 1 1 calc R U . . .
C16 C 0.95879(11) 0.29338(9) 0.41630(11) 0.0310(3) Uani 1 1 d . . . . .
H16 H 1.029095 0.252577 0.460067 0.037 Uiso 1 1 calc R U . . .
C17 C 0.90881(11) 0.27900(9) 0.31016(11) 0.0299(3) Uani 1 1 d . . . . .
H17 H 0.938504 0.224141 0.280481 0.036 Uiso 1 1 calc R U . . .
C11 C 0.77652(13) 0.60500(10) 0.60547(9) 0.0325(3) Uani 1 1 d . . . . .
H11 H 0.828508 0.627472 0.675501 0.039 Uiso 1 1 calc R U . . .
C14 C 0.97348(11) 0.39171(10) 0.57467(10) 0.0322(3) Uani 1 1 d . . . . .
H14 H 1.045784 0.352334 0.617337 0.039 Uiso 1 1 calc R U . . .
C28 C 0.16785(11) 0.51196(10) 0.11305(10) 0.0307(3) Uani 1 1 d . . . . .
H28 H 0.113871 0.468397 0.057394 0.037 Uiso 1 1 calc R U . . .
C19 C 0.77323(11) 0.34422(9) 0.13077(10) 0.0293(3) Uani 1 1 d . . . . .
H19 H 0.804172 0.291007 0.100146 0.035 Uiso 1 1 calc R U . . .
C8 C 0.45845(12) 0.65964(9) 0.39558(10) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.439788 0.722064 0.422775 0.036 Uiso 1 1 calc R U . . .
C13 C 0.93323(12) 0.46926(11) 0.61914(9) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.983731 0.490058 0.690107 0.040 Uiso 1 1 calc R U . . .
C10 C 0.66608(13) 0.65416(10) 0.54971(10) 0.0316(3) Uani 1 1 d . . . . .
H10 H 0.647211 0.717283 0.575598 0.038 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 O1 C27 118.66(8) . . ?
C21 C22 C23 121.72(10) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
O1 C2 C3 122.45(10) . . ?
O1 C2 C1 116.01(9) . . ?
C3 C2 C1 121.41(10) . . ?
C22 C23 C18 117.31(10) . . ?
C22 C23 C24 122.81(9) . . ?
C18 C23 C24 119.44(10) . . ?
C15 C24 C25 118.46(10) . . ?
C15 C24 C23 117.16(10) . . ?
C25 C24 C23 124.14(9) . . ?
C9 C26 C25 117.56(10) . . ?
C9 C26 C1 117.17(10) . . ?
C25 C26 C1 125.25(10) . . ?
C6 C1 C2 117.42(9) . . ?
C6 C1 C26 119.83(10) . . ?
C2 C1 C26 122.43(10) . . ?
C1 C6 C5 119.47(10) . . ?
C1 C6 C7 118.60(10) . . ?
C5 C6 C7 121.83(10) . . ?
C2 C3 C4 119.15(10) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C12 C25 C24 117.35(10) . . ?
C12 C25 C26 117.23(10) . . ?
C24 C25 C26 125.41(9) . . ?
C22 C21 C20 120.23(11) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C26 C9 C8 119.37(10) . . ?
C26 C9 C10 120.12(11) . . ?
C8 C9 C10 120.51(11) . . ?
C4 C5 C6 119.29(10) . . ?
C4 C5 C28 114.79(11) . . ?
C6 C5 C28 125.89(11) . . ?
C19 C18 C23 119.53(10) . . ?
C19 C18 C17 120.64(11) . . ?
C23 C18 C17 119.65(11) . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C12 C11 119.73(11) . . ?
C25 C12 C13 119.47(12) . . ?
C11 C12 C13 120.78(11) . . ?
C5 C4 C3 122.03(10) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C8 C7 C6 120.01(11) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C24 C15 C14 119.70(11) . . ?
C24 C15 C16 120.20(11) . . ?
C14 C15 C16 120.01(11) . . ?
C19 C20 C21 119.66(11) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C17 C16 C15 121.54(11) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.00(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C10 C11 C12 120.86(11) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C14 C15 120.56(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
O2 C28 C5 128.58(13) . . ?
O2 C28 H28 115.7 . . ?
C5 C28 H28 115.7 . . ?
C20 C19 C18 121.20(11) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C7 C8 C9 122.23(11) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C14 C13 C12 120.76(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C10 C9 120.12(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
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
O1 C2 1.3489(12) . ?
O1 C27 1.4347(13) . ?
O2 C28 1.2166(16) . ?
C22 C21 1.3764(15) . ?
C22 C23 1.4138(14) . ?
C22 H22 0.9500 . ?
C2 C3 1.3842(14) . ?
C2 C1 1.4328(15) . ?
C23 C18 1.4232(15) . ?
C23 C24 1.4525(14) . ?
C24 C15 1.4093(15) . ?
C24 C25 1.4435(15) . ?
C26 C9 1.4142(15) . ?
C26 C25 1.4506(15) . ?
C26 C1 1.4536(14) . ?
C1 C6 1.4222(15) . ?
C6 C5 1.4331(16) . ?
C6 C7 1.4360(15) . ?
C3 C4 1.3904(15) . ?
C3 H3 0.9500 . ?
C25 C12 1.4204(15) . ?
C21 C20 1.4038(17) . ?
C21 H21 0.9500 . ?
C9 C8 1.4218(17) . ?
C9 C10 1.4280(17) . ?
C5 C4 1.3819(16) . ?
C5 C28 1.4711(15) . ?
C18 C19 1.4154(17) . ?
C18 C17 1.4295(16) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C12 C11 1.4207(18) . ?
C12 C13 1.4255(18) . ?
C4 H4 0.9500 . ?
C7 C8 1.3541(18) . ?
C7 H7 0.9500 . ?
C15 C14 1.4228(17) . ?
C15 C16 1.4295(18) . ?
C20 C19 1.3656(18) . ?
C20 H20 0.9500 . ?
C16 C17 1.3478(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C11 C10 1.351(2) . ?
C11 H11 0.9500 . ?
C14 C13 1.353(2) . ?
C14 H14 0.9500 . ?
C28 H28 0.9500 . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C27 O1 C2 C3 15.03(14) . . . . ?
C27 O1 C2 C1 -168.95(9) . . . . ?
C21 C22 C23 C18 4.27(15) . . . . ?
C21 C22 C23 C24 176.62(10) . . . . ?
C22 C23 C24 C15 -157.63(10) . . . . ?
C18 C23 C24 C15 14.57(14) . . . . ?
C22 C23 C24 C25 16.69(15) . . . . ?
C18 C23 C24 C25 -171.11(9) . . . . ?
O1 C2 C1 C6 -163.70(9) . . . . ?
C3 C2 C1 C6 12.37(15) . . . . ?
O1 C2 C1 C26 9.77(14) . . . . ?
C3 C2 C1 C26 -174.15(10) . . . . ?
C9 C26 C1 C6 18.91(14) . . . . ?
C25 C26 C1 C6 -162.82(10) . . . . ?
C9 C26 C1 C2 -154.42(10) . . . . ?
C25 C26 C1 C2 23.86(16) . . . . ?
C2 C1 C6 C5 -11.54(15) . . . . ?
C26 C1 C6 C5 174.81(9) . . . . ?
C2 C1 C6 C7 164.82(9) . . . . ?
C26 C1 C6 C7 -8.83(15) . . . . ?
O1 C2 C3 C4 170.91(9) . . . . ?
C1 C2 C3 C4 -4.91(15) . . . . ?
C15 C24 C25 C12 22.66(14) . . . . ?
C23 C24 C25 C12 -151.59(10) . . . . ?
C15 C24 C25 C26 -158.00(10) . . . . ?
C23 C24 C25 C26 27.75(16) . . . . ?
C9 C26 C25 C12 24.24(14) . . . . ?
C1 C26 C25 C12 -154.03(10) . . . . ?
C9 C26 C25 C24 -155.11(10) . . . . ?
C1 C26 C25 C24 26.63(16) . . . . ?
C23 C22 C21 C20 0.84(16) . . . . ?
C25 C26 C9 C8 166.04(10) . . . . ?
C1 C26 C9 C8 -15.55(15) . . . . ?
C25 C26 C9 C10 -14.02(15) . . . . ?
C1 C26 C9 C10 164.39(10) . . . . ?
C1 C6 C5 C4 3.65(15) . . . . ?
C7 C6 C5 C4 -172.59(10) . . . . ?
C1 C6 C5 C28 -178.58(10) . . . . ?
C7 C6 C5 C28 5.18(17) . . . . ?
C22 C23 C18 C19 -6.72(15) . . . . ?
C24 C23 C18 C19 -179.35(9) . . . . ?
C22 C23 C18 C17 168.43(9) . . . . ?
C24 C23 C18 C17 -4.19(15) . . . . ?
C24 C25 C12 C11 161.38(10) . . . . ?
C26 C25 C12 C11 -18.02(15) . . . . ?
C24 C25 C12 C13 -16.98(15) . . . . ?
C26 C25 C12 C13 163.62(10) . . . . ?
C6 C5 C4 C3 4.22(16) . . . . ?
C28 C5 C4 C3 -173.80(10) . . . . ?
C2 C3 C4 C5 -3.63(16) . . . . ?
C1 C6 C7 C8 -4.98(16) . . . . ?
C5 C6 C7 C8 171.29(11) . . . . ?
C25 C24 C15 C14 -13.23(15) . . . . ?
C23 C24 C15 C14 161.42(10) . . . . ?
C25 C24 C15 C16 170.31(10) . . . . ?
C23 C24 C15 C16 -15.04(15) . . . . ?
C22 C21 C20 C19 -3.55(17) . . . . ?
C24 C15 C16 C17 4.96(17) . . . . ?
C14 C15 C16 C17 -171.48(11) . . . . ?
C15 C16 C17 C18 6.05(17) . . . . ?
C19 C18 C17 C16 168.81(11) . . . . ?
C23 C18 C17 C16 -6.29(16) . . . . ?
C25 C12 C11 C10 0.80(16) . . . . ?
C13 C12 C11 C10 179.14(11) . . . . ?
C24 C15 C14 C13 -2.52(17) . . . . ?
C16 C15 C14 C13 173.94(11) . . . . ?
C4 C5 C28 O2 176.67(12) . . . . ?
C6 C5 C28 O2 -1.2(2) . . . . ?
C21 C20 C19 C18 0.96(17) . . . . ?
C23 C18 C19 C20 4.26(16) . . . . ?
C17 C18 C19 C20 -170.84(11) . . . . ?
C6 C7 C8 C9 8.54(18) . . . . ?
C26 C9 C8 C7 2.10(17) . . . . ?
C10 C9 C8 C7 -177.83(11) . . . . ?
C15 C14 C13 C12 8.54(17) . . . . ?
C25 C12 C13 C14 1.52(17) . . . . ?
C11 C12 C13 C14 -176.82(11) . . . . ?
C12 C11 C10 C9 10.15(17) . . . . ?
C26 C9 C10 C11 -3.28(16) . . . . ?
C8 C9 C10 C11 176.65(11) . . . . ?
