# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3bi
_database_code_depnum_ccdc_archive 'CCDC 1970436'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-((5-isopropyl-3,8-dimethylazulen-1-yl)hexa-1,3,5-triyn-1-yl)benzonitrile
_chemical_formula_moiety         'C28 H21 N'
_chemical_formula_sum            'C28 H21 N'
_chemical_formula_weight         371.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.156(3)
_cell_length_b                   8.911(3)
_cell_length_c                   15.671(5)
_cell_angle_alpha                101.68(2)
_cell_angle_beta                 96.05(3)
_cell_angle_gamma                113.08(3)
_cell_volume                     1004.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3071
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.5755
_cell_measurement_theta_min      3.1288
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 10 -9 0.1495
8 -6 14 0.1009
-7 8 -15 0.1428
-2 -10 11 0.2452

_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.1329 9.6962 -8.6908 0.0922 -0.2439 0.9654
8.0597 -5.9769 14.0244 0.3638 -0.8621 -0.3528
-6.7615 8.1518 -15.4573 -0.3180 0.7470 0.5838
-1.7260 -10.3900 10.7276 -0.0302 0.0961 -0.9949

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7183
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  70.75   0.75   55.00    --   30.00 -79.00   0.00  193
  2  ω    -74.00  70.75   0.75   55.00    --   30.00 -79.00  90.00  193
  3  ω    -74.00  70.75   0.75   55.00    --   30.00 -79.00 180.00  193
  4  ω    -10.00  71.00   0.75   55.00    --   30.00 -79.00 270.00  108
  5  ω    -54.00 -47.25   0.75   65.00    --   48.00 -79.00  45.00    9
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  Kuma
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0599330000
_diffrn_orient_matrix_UB_12      -0.0282766000
_diffrn_orient_matrix_UB_13      -0.0205555000
_diffrn_orient_matrix_UB_21      -0.0664781000
_diffrn_orient_matrix_UB_22      -0.0396958000
_diffrn_orient_matrix_UB_23      -0.0401842000
_diffrn_orient_matrix_UB_31      0.0362952000
_diffrn_orient_matrix_UB_32      0.0753929000
_diffrn_orient_matrix_UB_33      -0.0138838000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2926
_reflns_number_total             3889
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      1.028
_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)+(0.1106P)²+0.4123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.2013
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C23(H23), C8(H8), C11(H11), C12(H12), C15(H15), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N1 N -0.7184(3) -0.5288(3) 0.12891(15) 0.0371(5) Uani 1 1 d . . . . .
C18 C 0.8678(3) 1.1246(3) 0.73060(14) 0.0225(5) Uani 1 1 d . . . . .
C10 C -0.4706(3) -0.2571(3) 0.24086(15) 0.0240(5) Uani 1 1 d . . . . .
C9 C -0.4481(3) -0.0981(3) 0.23127(15) 0.0244(5) Uani 1 1 d . . . . .
H9 H -0.526769 -0.089125 0.185338 0.029 Uiso 1 1 calc R . . . .
C7 C -0.1930(3) 0.0336(3) 0.35622(15) 0.0241(5) Uani 1 1 d . . . . .
C23 C 1.1159(3) 1.3832(3) 0.85119(16) 0.0261(5) Uani 1 1 d . . . . .
H23 H 1.199798 1.409774 0.904867 0.031 Uiso 1 1 calc R . . . .
C16 C 1.0225(3) 1.0846(3) 0.85271(15) 0.0261(5) Uani 1 1 d . . . . .
C13 C -0.6095(3) -0.4078(3) 0.17909(16) 0.0281(5) Uani 1 1 d . . . . .
C8 C -0.3113(3) 0.0455(3) 0.28876(15) 0.0262(5) Uani 1 1 d . . . . .
H8 H -0.296856 0.153655 0.282707 0.031 Uiso 1 1 calc R . . . .
C5 C 0.0799(3) 0.3070(3) 0.46115(16) 0.0281(5) Uani 1 1 d . . . . .
C11 C -0.3560(3) -0.2705(3) 0.30887(16) 0.0289(5) Uani 1 1 d . . . . .
H11 H -0.372905 -0.378687 0.315821 0.035 Uiso 1 1 calc R . . . .
C17 C 1.0119(3) 1.2120(3) 0.81252(15) 0.0248(5) Uani 1 1 d . . . . .
C3 C 0.3608(3) 0.5639(3) 0.56202(16) 0.0290(5) Uani 1 1 d . . . . .
C12 C -0.2185(3) -0.1264(3) 0.36584(16) 0.0290(5) Uani 1 1 d . . . . .
H12 H -0.140495 -0.135768 0.411942 0.035 Uiso 1 1 calc R . . . .
C22 C 1.1167(3) 1.5225(3) 0.82359(15) 0.0260(5) Uani 1 1 d . . . . .
C15 C 0.8874(3) 0.9290(3) 0.80175(16) 0.0293(5) Uani 1 1 d . . . . .
H15 H 0.862683 0.823597 0.814813 0.035 Uiso 1 1 calc R . . . .
C4 C 0.2263(3) 0.4440(3) 0.51455(16) 0.0293(5) Uani 1 1 d . . . . .
C1 C 0.6421(3) 0.8159(3) 0.66599(17) 0.0308(6) Uani 1 1 d . . . . .
C2 C 0.5105(3) 0.6959(3) 0.61711(17) 0.0309(6) Uani 1 1 d . . . . .
C26 C 1.2362(3) 1.6987(3) 0.88612(16) 0.0281(5) Uani 1 1 d . . . . .
H26 H 1.205256 1.781758 0.861601 0.034 Uiso 1 1 calc R . . . .
C19 C 0.8241(3) 1.2028(3) 0.66660(15) 0.0288(5) Uani 1 1 d . . . . .
C14 C 0.7918(3) 0.9509(3) 0.72728(16) 0.0278(5) Uani 1 1 d . . . . .
C6 C -0.0472(3) 0.1827(3) 0.41338(16) 0.0284(5) Uani 1 1 d . . . . .
C27 C 1.1970(3) 1.7153(3) 0.98024(16) 0.0330(6) Uani 1 1 d . . . . .
H27A H 1.066591 1.683515 0.977052 0.050 Uiso 1 1 calc GR . . . .
H27B H 1.266581 1.832596 1.016062 0.050 Uiso 1 1 calc GR . . . .
H27C H 1.232609 1.640254 1.007789 0.050 Uiso 1 1 calc GR . . . .
C20 C 0.8966(3) 1.3748(3) 0.67446(16) 0.0325(6) Uani 1 1 d . . . . .
H20 H 0.855594 1.403764 0.623837 0.039 Uiso 1 1 calc R . . . .
C24 C 1.1551(3) 1.1135(3) 0.93422(15) 0.0296(5) Uani 1 1 d . . . . .
H24A H 1.278395 1.153682 0.922096 0.044 Uiso 1 1 calc GR . . . .
H24B H 1.124636 1.007267 0.951183 0.044 Uiso 1 1 calc GR . . . .
H24C H 1.149547 1.198670 0.982941 0.044 Uiso 1 1 calc GR . . . .
C28 C 1.4363(3) 1.7457(3) 0.88764(19) 0.0357(6) Uani 1 1 d . . . . .
H28A H 1.473372 1.670877 0.914620 0.053 Uiso 1 1 calc GR . . . .
H28B H 1.508198 1.863348 0.922637 0.053 Uiso 1 1 calc GR . . . .
H28C H 1.456998 1.733462 0.826629 0.053 Uiso 1 1 calc GR . . . .
C25 C 0.6875(3) 1.0938(3) 0.58295(16) 0.0368(6) Uani 1 1 d . . . . .
H25A H 0.718719 1.001773 0.556130 0.055 Uiso 1 1 calc GR . . . .
H25B H 0.687924 1.161952 0.541059 0.055 Uiso 1 1 calc GR . . . .
H25C H 0.566085 1.045987 0.596785 0.055 Uiso 1 1 calc GR . . . .
C21 C 1.0192(3) 1.5142(3) 0.74317(16) 0.0305(5) Uani 1 1 d . . . . .
H21 H 1.039025 1.621048 0.733143 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N1 C13 1.153(3) . ?
C18 C17 1.482(3) . ?
C18 C19 1.422(3) . ?
C18 C14 1.411(3) . ?
C10 C9 1.397(3) . ?
C10 C13 1.439(3) . ?
C10 C11 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.377(3) . ?
C7 C8 1.404(3) . ?
C7 C12 1.400(3) . ?
C7 C6 1.427(3) . ?
C23 H23 0.9500 . ?
C23 C17 1.384(3) . ?
C23 C22 1.393(3) . ?
C16 C17 1.431(3) . ?
C16 C15 1.394(3) . ?
C16 C24 1.492(3) . ?
C8 H8 0.9500 . ?
C5 C4 1.360(3) . ?
C5 C6 1.209(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(3) . ?
C3 C4 1.218(3) . ?
C3 C2 1.364(3) . ?
C12 H12 0.9500 . ?
C22 C26 1.533(3) . ?
C22 C21 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.424(4) . ?
C1 C2 1.215(3) . ?
C1 C14 1.412(3) . ?
C26 H26 1.0000 . ?
C26 C27 1.532(3) . ?
C26 C28 1.514(3) . ?
C19 C20 1.382(3) . ?
C19 C25 1.494(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.400(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C21 H21 0.9500 . ?

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
C19 C18 C17 125.6(2) . . ?
C14 C18 C17 106.6(2) . . ?
C14 C18 C19 127.7(2) . . ?
C9 C10 C13 119.9(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 C13 119.9(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C8 C7 C6 120.3(2) . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 C6 120.5(2) . . ?
C17 C23 H23 115.0 . . ?
C17 C23 C22 130.0(2) . . ?
C22 C23 H23 115.0 . . ?
C17 C16 C24 126.0(2) . . ?
C15 C16 C17 107.7(2) . . ?
C15 C16 C24 126.3(2) . . ?
N1 C13 C10 178.8(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C6 C5 C4 178.2(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C23 C17 C18 130.1(2) . . ?
C23 C17 C16 122.6(2) . . ?
C16 C17 C18 107.23(19) . . ?
C4 C3 C2 178.4(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C23 C22 C26 117.6(2) . . ?
C21 C22 C23 125.0(2) . . ?
C21 C22 C26 117.4(2) . . ?
C16 C15 H15 124.9 . . ?
C16 C15 C14 110.2(2) . . ?
C14 C15 H15 124.9 . . ?
C3 C4 C5 177.9(2) . . ?
C2 C1 C14 176.4(3) . . ?
C1 C2 C3 178.5(3) . . ?
C22 C26 H26 107.2 . . ?
C27 C26 C22 112.24(18) . . ?
C27 C26 H26 107.2 . . ?
C28 C26 C22 111.35(18) . . ?
C28 C26 H26 107.2 . . ?
C28 C26 C27 111.4(2) . . ?
C18 C19 C25 118.8(2) . . ?
C20 C19 C18 125.7(2) . . ?
C20 C19 C25 115.5(2) . . ?
C18 C14 C15 108.2(2) . . ?
C18 C14 C1 128.9(2) . . ?
C1 C14 C15 122.8(2) . . ?
C5 C6 C7 178.0(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C20 H20 114.0 . . ?
C19 C20 C21 132.0(2) . . ?
C21 C20 H20 114.0 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C21 C20 130.8(2) . . ?
C22 C21 H21 114.6 . . ?
C20 C21 H21 114.6 . . ?

_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.787
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3bj
_database_code_depnum_ccdc_archive 'CCDC 1970438'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O2'
_chemical_formula_sum            'C27 H21 N O2'
_chemical_formula_weight         391.47
# start Validation Reply Form
_vrf_PLAT026_3bj                 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        35% Check 
RESPONSE: 'Low quality of crystals. One of two molecules in asymmetric unit is strongly
disordered'
;
_vrf_PLAT097_3bj                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.03 eA-3  
RESPONSE: One of two molecules in asymmetric unit is strongly disordered
;
_vrf_PLAT201_3bj                 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          3 Report
RESPONSE: One of two molecules in asymmetric unit is strongly disordered
;
# end Validation Reply Form

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.653(2)
_cell_length_b                   16.102(5)
_cell_length_c                   17.021(5)
_cell_angle_alpha                76.24(3)
_cell_angle_beta                 89.86(3)
_cell_angle_gamma                81.03(3)
_cell_volume                     2011.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1751
_cell_measurement_theta_min      2.8002
_cell_measurement_theta_max      27.3953

_exptl_crystal_description       plates
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'KUMA KM4 CCDC'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            13846
_diffrn_reflns_av_unetI/netI     0.2094
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             8101
_reflns_number_gt                2815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0945P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8101
_refine_ls_number_parameters     602
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.2463
_refine_ls_R_factor_gt           0.0971
_refine_ls_wR_factor_ref         0.3030
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1A O 1.0735(5) 0.7483(3) 1.3982(2) 0.0475(11) Uani 1 1 d . . . . .
O2A O 1.0975(5) 0.8467(3) 1.2890(2) 0.0523(12) Uani 1 1 d . . . . .
N1A N 1.0655(6) 0.7754(3) 1.3238(3) 0.0386(12) Uani 1 1 d . . . . .
C1A C 0.5878(7) 0.3202(3) 0.9294(3) 0.0315(13) Uani 1 1 d . . . . .
C2A C 0.6403(7) 0.3658(4) 0.9684(4) 0.0381(14) Uani 1 1 d . . . . .
C3A C 0.6997(7) 0.4191(4) 1.0105(4) 0.0408(15) Uani 1 1 d . . . . .
C4A C 0.7525(7) 0.4645(4) 1.0501(4) 0.0415(16) Uani 1 1 d . . . . .
C5A C 0.8086(7) 0.5166(4) 1.0940(4) 0.0414(15) Uani 1 1 d . . . . .
C6A C 0.8540(7) 0.5617(4) 1.1347(4) 0.0392(15) Uani 1 1 d . . . . .
C7A C 0.9092(6) 0.6161(3) 1.1821(3) 0.0267(12) Uani 1 1 d . . . . .
C8A C 0.9664(7) 0.6933(3) 1.1455(3) 0.0330(13) Uani 1 1 d . . . . .
H8A H 0.9698 0.7102 1.0882 0.040 Uiso 1 1 calc R U . . .
C9A C 1.0187(7) 0.7458(3) 1.1917(3) 0.0329(13) Uani 1 1 d . . . . .
H9A H 1.0573 0.7990 1.1670 0.039 Uiso 1 1 calc R U . . .
C10A C 1.0131(7) 0.7185(3) 1.2751(3) 0.0299(13) Uani 1 1 d . . . . .
C11A C 0.9599(7) 0.6417(3) 1.3138(3) 0.0347(14) Uani 1 1 d . . . . .
H11A H 0.9590 0.6246 1.3712 0.042 Uiso 1 1 calc R U . . .
C12A C 0.9077(6) 0.5903(3) 1.2667(3) 0.0337(13) Uani 1 1 d . . . . .
H12A H 0.8706 0.5370 1.2919 0.040 Uiso 1 1 calc R U . . .
C13A C 0.5240(7) 0.2628(3) 0.8898(3) 0.0310(13) Uani 1 1 d . . . . .
C14A C 0.4685(6) 0.1848(3) 0.9332(3) 0.0320(13) Uani 1 1 d . . . . .
H14A H 0.4667 0.1668 0.9906 0.038 Uiso 1 1 calc R U . . .
C15A C 0.4177(6) 0.1389(3) 0.8808(3) 0.0288(12) Uani 1 1 d . . . . .
C16A C 0.4425(6) 0.1864(3) 0.7997(3) 0.0287(12) Uani 1 1 d . . . . .
C17A C 0.4186(6) 0.1555(3) 0.7325(3) 0.0301(13) Uani 1 1 d . . . . .
H17A H 0.3826 0.1001 0.7439 0.036 Uiso 1 1 calc R U . . .
C18A C 0.4382(7) 0.1914(3) 0.6502(3) 0.0323(13) Uani 1 1 d . . . . .
C19A C 0.4781(7) 0.2745(3) 0.6198(3) 0.0343(13) Uani 1 1 d . . . . .
H19A H 0.4794 0.2918 0.5625 0.041 Uiso 1 1 calc R U . . .
C20A C 0.5160(6) 0.3355(3) 0.6589(3) 0.0313(13) Uani 1 1 d . . . . .
H20A H 0.5351 0.3880 0.6230 0.038 Uiso 1 1 calc R U . . .
C21A C 0.5323(6) 0.3359(3) 0.7411(3) 0.0294(13) Uani 1 1 d . . . . .
C22A C 0.5049(6) 0.2683(3) 0.8054(3) 0.0301(13) Uani 1 1 d . . . . .
C23A C 0.5805(7) 0.4177(3) 0.7581(3) 0.0350(14) Uani 1 1 d . . . . .
H23G H 0.6931 0.4039 0.7893 0.052 Uiso 1 1 calc R U . . .
H23H H 0.4875 0.4428 0.7892 0.052 Uiso 1 1 calc R U . . .
H23I H 0.5922 0.4595 0.7068 0.052 Uiso 1 1 calc R U . . .
C24A C 0.4240(7) 0.1357(4) 0.5903(3) 0.0371(14) Uani 1 1 d . . . . .
H24A H 0.3912 0.1764 0.5363 0.044 Uiso 1 1 calc R U . . .
C25A C 0.2837(7) 0.0763(3) 0.6075(3) 0.0391(14) Uani 1 1 d . . . . .
H25G H 0.3188 0.0306 0.6567 0.059 Uiso 1 1 calc R U . . .
H25H H 0.2728 0.0500 0.5617 0.059 Uiso 1 1 calc R U . . .
H25I H 0.1696 0.1101 0.6151 0.059 Uiso 1 1 calc R U . . .
C26A C 0.6054(7) 0.0842(4) 0.5827(4) 0.0498(17) Uani 1 1 d . . . . .
H26G H 0.6935 0.1233 0.5726 0.075 Uiso 1 1 calc R U . . .
H26H H 0.6013 0.0564 0.5375 0.075 Uiso 1 1 calc R U . . .
H26I H 0.6381 0.0398 0.6329 0.075 Uiso 1 1 calc R U . . .
C27A C 0.3454(7) 0.0553(3) 0.9026(3) 0.0339(13) Uani 1 1 d . . . . .
H27G H 0.3543 0.0326 0.9615 0.051 Uiso 1 1 calc R U . . .
H27H H 0.4136 0.0133 0.8765 0.051 Uiso 1 1 calc R U . . .
H27I H 0.2210 0.0655 0.8841 0.051 Uiso 1 1 calc R U . . .
O1B O 0.4999(6) 0.9130(3) 0.7632(2) 0.0522(12) Uani 1 1 d . . . . .
O2B O 0.4330(6) 0.8232(3) 0.8710(3) 0.0590(13) Uani 1 1 d . . . . .
N1B N 0.4532(6) 0.8444(3) 0.7978(3) 0.0406(12) Uani 1 1 d . . . . .
C2B C 0.1964(6) 0.4162(3) 0.4258(3) 0.0317(13) Uani 1 1 d . . . . .
C3B C 0.2290(6) 0.4702(3) 0.4717(3) 0.0329(13) Uani 1 1 d . . . . .
C4B C 0.2547(7) 0.5186(4) 0.5149(3) 0.0354(14) Uani 1 1 d . . . . .
C5B C 0.2865(7) 0.5714(4) 0.5628(3) 0.0350(14) Uani 1 1 d . . . . .
C6B C 0.3136(7) 0.6168(4) 0.6066(3) 0.0364(14) Uani 1 1 d . . . . .
C7B C 0.3465(6) 0.6746(3) 0.6563(3) 0.0281(12) Uani 1 1 d . . . . .
C8B C 0.4175(7) 0.7492(3) 0.6213(3) 0.0353(14) Uani 1 1 d . . . . .
H8B H 0.4415 0.7615 0.5653 0.042 Uiso 1 1 calc R U . . .
C9B C 0.4530(7) 0.8049(3) 0.6664(3) 0.0343(13) Uani 1 1 d . . . . .
H9B H 0.5014 0.8556 0.6425 0.041 Uiso 1 1 calc R U . . .
C10B C 0.4168(6) 0.7856(3) 0.7473(3) 0.0315(13) Uani 1 1 d . . . . .
C11B C 0.3457(7) 0.7123(4) 0.7856(3) 0.0359(14) Uani 1 1 d . . . . .
H11B H 0.3223 0.7007 0.8417 0.043 Uiso 1 1 calc R U . . .
C12B C 0.3104(7) 0.6569(4) 0.7381(3) 0.0358(14) Uani 1 1 d . . . . .
H12B H 0.2612 0.6065 0.7619 0.043 Uiso 1 1 calc R U . . .
C1B C 0.1675(19) 0.3624(9) 0.3915(8) 0.032(3) Uani 0.680(6) 1 d . U P A 1
C13B C 0.1231(10) 0.2958(5) 0.3609(5) 0.034(2) Uani 0.680(6) 1 d . U P A 1
C14B C 0.0675(14) 0.2243(8) 0.4153(8) 0.045(3) Uani 0.680(6) 1 d . U P A 1
H14B H 0.0519 0.2204 0.4714 0.054 Uiso 0.680(6) 1 calc R U P A 1
C15B C 0.0391(12) 0.1617(7) 0.3768(7) 0.039(3) Uani 0.680(6) 1 d . U P A 1
C16B C 0.0748(10) 0.1923(5) 0.2930(6) 0.038(2) Uani 0.680(6) 1 d . U P A 1
C17B C 0.0526(13) 0.1447(7) 0.2377(7) 0.060(3) Uani 0.680(6) 1 d . U P A 1
H17B H 0.0132 0.0909 0.2587 0.072 Uiso 0.680(6) 1 calc R U P A 1
C18B C 0.0814(17) 0.1658(8) 0.1516(8) 0.074(4) Uani 0.680(6) 1 d D U P A 1
C19B C 0.1315(15) 0.2403(7) 0.1103(7) 0.074(4) Uani 0.680(6) 1 d . U P A 1
H19B H 0.1402 0.2446 0.0539 0.088 Uiso 0.680(6) 1 calc R U P A 1
C20B C 0.1733(14) 0.3130(8) 0.1342(7) 0.061(3) Uani 0.680(6) 1 d . U P A 1
H20B H 0.2053 0.3566 0.0909 0.073 Uiso 0.680(6) 1 calc R U P A 1
C21B C 0.1767(12) 0.3328(6) 0.2083(7) 0.036(3) Uani 0.680(6) 1 d . U P A 1
C22B C 0.1286(14) 0.2799(7) 0.2811(7) 0.030(3) Uani 0.680(6) 1 d . U P A 1
C23B C 0.2249(15) 0.4186(7) 0.2130(7) 0.042(3) Uani 0.680(6) 1 d . U P A 1
H23A H 0.2549 0.4498 0.1592 0.063 Uiso 0.680(6) 1 calc R U P A 1
H23B H 0.3269 0.4089 0.2506 0.063 Uiso 0.680(6) 1 calc R U P A 1
H23C H 0.1242 0.4530 0.2323 0.063 Uiso 0.680(6) 1 calc R U P A 1
C24B C 0.0381(15) 0.0878(7) 0.1169(7) 0.073(3) Uiso 0.680(6) 1 d D . P A 1
H24B H -0.0636 0.0698 0.1501 0.088 Uiso 0.680(6) 1 calc R U P A 1
C26B C 0.1749(13) 0.0074(7) 0.1397(7) 0.036(3) Uiso 0.680(6) 1 d D . P A 1
H26A H 0.1595 -0.0309 0.1042 0.054 Uiso 0.680(6) 1 calc R U P A 1
H26B H 0.1609 -0.0227 0.1960 0.054 Uiso 0.680(6) 1 calc R U P A 1
H26C H 0.2935 0.0234 0.1337 0.054 Uiso 0.680(6) 1 calc R U P A 1
C25B C -0.0469(15) 0.1220(7) 0.0351(6) 0.043(3) Uiso 0.680(6) 1 d D . P A 1
H25A H 0.0365 0.1502 -0.0018 0.064 Uiso 0.680(6) 1 calc R U P A 1
H25B H -0.1526 0.1642 0.0376 0.064 Uiso 0.680(6) 1 calc R U P A 1
H25C H -0.0809 0.0742 0.0152 0.064 Uiso 0.680(6) 1 calc R U P A 1
C27B C -0.0219(11) 0.0780(5) 0.4143(6) 0.054(3) Uani 0.680(6) 1 d . U P A 1
H27A H -0.0273 0.0710 0.4730 0.081 Uiso 0.680(6) 1 calc R U P A 1
H27B H 0.0613 0.0301 0.4026 0.081 Uiso 0.680(6) 1 calc R U P A 1
H27C H -0.1397 0.0781 0.3918 0.081 Uiso 0.680(6) 1 calc R U P A 1
C1C C 0.167(4) 0.3810(18) 0.3719(17) 0.021(7) Uiso 0.320(6) 1 d . . P A 2
C13C C 0.1549(19) 0.3402(10) 0.3050(10) 0.023(4) Uiso 0.320(6) 1 d . . P A 2
C14C C 0.205(3) 0.3846(15) 0.2261(14) 0.025(5) Uiso 0.320(6) 1 d . . P A 2
H14C H 0.2501 0.4377 0.2152 0.030 Uiso 0.320(6) 1 calc R U P A 2
C15C C 0.177(3) 0.3388(15) 0.1676(15) 0.028(6) Uiso 0.320(6) 1 d . . P A 2
C16C C 0.1219(19) 0.2625(10) 0.2086(9) 0.021(4) Uiso 0.320(6) 1 d . . P A 2
C17C C 0.094(3) 0.1988(14) 0.1721(14) 0.034(5) Uiso 0.320(6) 1 d . . P A 2
H17C H 0.1175 0.2126 0.1160 0.041 Uiso 0.320(6) 1 calc R U P A 2
C18C C 0.043(2) 0.1227(11) 0.1958(11) 0.022(4) Uiso 0.320(6) 1 d D . P A 2
C19C C 0.0055(19) 0.0818(10) 0.2771(9) 0.023(4) Uiso 0.320(6) 1 d . . P A 2
H19C H -0.0275 0.0261 0.2846 0.027 Uiso 0.320(6) 1 calc R U P A 2
C20C C 0.011(2) 0.1128(12) 0.3456(12) 0.035(5) Uiso 0.320(6) 1 d . . P A 2
H20C H -0.0210 0.0756 0.3939 0.042 Uiso 0.320(6) 1 calc R U P A 2
C21C C 0.057(3) 0.1934(14) 0.3549(14) 0.027(6) Uiso 0.320(6) 1 d . . P A 2
C22C C 0.102(3) 0.2596(15) 0.2994(14) 0.017(6) Uiso 0.320(6) 1 d . . P A 2
C23C C 0.045(3) 0.2080(17) 0.4421(12) 0.024(6) Uiso 0.320(6) 1 d . . P A 2
H23D H 0.0098 0.1571 0.4789 0.037 Uiso 0.320(6) 1 calc R U P A 2
H23E H -0.0429 0.2592 0.4421 0.037 Uiso 0.320(6) 1 calc R U P A 2
H23F H 0.1608 0.2169 0.4602 0.037 Uiso 0.320(6) 1 calc R U P A 2
C24C C 0.010(3) 0.0607(14) 0.1434(12) 0.073(3) Uiso 0.320(6) 1 d D . P A 2
H24C H -0.0639 0.0165 0.1696 0.088 Uiso 0.320(6) 1 calc R U P A 2
C25C C -0.063(2) 0.1149(12) 0.0591(11) 0.022(5) Uiso 0.320(6) 1 d D . P A 2
H25D H -0.1666 0.1565 0.0653 0.033 Uiso 0.320(6) 1 calc R U P A 2
H25E H -0.0963 0.0764 0.0270 0.033 Uiso 0.320(6) 1 calc R U P A 2
H25F H 0.0288 0.1462 0.0315 0.033 Uiso 0.320(6) 1 calc R U P A 2
C26C C 0.190(3) 0.0226(18) 0.1223(16) 0.049(9) Uiso 0.320(6) 1 d D . P A 2
H26D H 0.2469 0.0683 0.0885 0.073 Uiso 0.320(6) 1 calc R U P A 2
H26E H 0.1786 -0.0216 0.0926 0.073 Uiso 0.320(6) 1 calc R U P A 2
H26F H 0.2621 -0.0040 0.1720 0.073 Uiso 0.320(6) 1 calc R U P A 2
C27C C 0.216(2) 0.3662(11) 0.0820(10) 0.034(4) Uiso 0.320(6) 1 d . . P A 2
H27D H 0.1050 0.3812 0.0493 0.051 Uiso 0.320(6) 1 calc R U P A 2
H27E H 0.2923 0.3189 0.0658 0.051 Uiso 0.320(6) 1 calc R U P A 2
H27F H 0.2758 0.4169 0.0736 0.051 Uiso 0.320(6) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1A N1A 1.236(5) . ?
O2A N1A 1.221(5) . ?
N1A C10A 1.472(6) . ?
C1A C2A 1.211(7) . ?
C1A C13A 1.410(7) . ?
C2A C3A 1.368(7) . ?
C3A C4A 1.216(7) . ?
C4A C5A 1.363(7) . ?
C5A C6A 1.203(7) . ?
C6A C7A 1.432(7) . ?
C7A C8A 1.386(7) . ?
C7A C12A 1.402(7) . ?
C8A C9A 1.385(7) . ?
C9A C10A 1.385(7) . ?
C10A C11A 1.377(7) . ?
C11A C12A 1.381(7) . ?
C13A C14A 1.424(7) . ?
C13A C22A 1.424(7) . ?
C14A C15A 1.377(6) . ?
C15A C16A 1.437(7) . ?
C15A C27A 1.501(6) . ?
C16A C17A 1.376(7) . ?
C16A C22A 1.495(7) . ?
C17A C18A 1.400(7) . ?
C18A C19A 1.395(7) . ?
C18A C24A 1.523(7) . ?
C19A C20A 1.375(7) . ?
C20A C21A 1.407(7) . ?
C21A C22A 1.390(7) . ?
C21A C23A 1.513(6) . ?
C24A C26A 1.525(7) . ?
C24A C25A 1.530(7) . ?
O1B N1B 1.227(6) . ?
O2B N1B 1.226(5) . ?
N1B C10B 1.478(6) . ?
C2B C1B 1.201(15) . ?
C2B C1C 1.23(3) . ?
C2B C3B 1.348(7) . ?
C3B C4B 1.228(7) . ?
C4B C5B 1.356(7) . ?
C5B C6B 1.202(7) . ?
C6B C7B 1.446(7) . ?
C7B C12B 1.390(7) . ?
C7B C8B 1.398(7) . ?
C8B C9B 1.367(7) . ?
C9B C10B 1.376(7) . ?
C10B C11B 1.395(7) . ?
C11B C12B 1.393(7) . ?
C1B C13B 1.384(16) . ?
C13B C14B 1.417(15) . ?
C13B C22B 1.441(14) . ?
C14B C15B 1.371(15) . ?
C15B C16B 1.436(14) . ?
C15B C27B 1.491(13) . ?
C16B C17B 1.372(13) . ?
C16B C22B 1.498(13) . ?
C17B C18B 1.447(17) . ?
C18B C19B 1.349(17) . ?
C18B C24B 1.588(12) . ?
C19B C20B 1.407(14) . ?
C20B C21B 1.374(13) . ?
C21B C22B 1.411(16) . ?
C21B C23B 1.503(13) . ?
C24B C25B 1.481(12) . ?
C24B C26B 1.504(11) . ?
C1C C13C 1.45(3) . ?
C13C C22C 1.44(3) . ?
C13C C14C 1.44(3) . ?
C14C C15C 1.41(3) . ?
C15C C16C 1.39(3) . ?
C15C C27C 1.46(3) . ?
C16C C17C 1.36(2) . ?
C16C C22C 1.54(3) . ?
C17C C18C 1.32(3) . ?
C18C C19C 1.43(2) . ?
C18C C24C 1.536(17) . ?
C19C C20C 1.38(2) . ?
C20C C21C 1.44(3) . ?
C21C C22C 1.33(3) . ?
C21C C23C 1.56(3) . ?
C24C C26C 1.496(18) . ?
C24C C25C 1.545(17) . ?

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
O2A N1A O1A 123.6(5) . . ?
O2A N1A C10A 118.7(5) . . ?
O1A N1A C10A 117.7(5) . . ?
C2A C1A C13A 175.6(6) . . ?
C1A C2A C3A 178.4(7) . . ?
C4A C3A C2A 178.0(7) . . ?
C3A C4A C5A 178.8(7) . . ?
C6A C5A C4A 177.8(7) . . ?
C5A C6A C7A 179.1(7) . . ?
C8A C7A C12A 119.6(4) . . ?
C8A C7A C6A 121.0(5) . . ?
C12A C7A C6A 119.4(5) . . ?
C9A C8A C7A 120.7(5) . . ?
C10A C9A C8A 117.9(5) . . ?
C11A C10A C9A 123.2(5) . . ?
C11A C10A N1A 119.1(5) . . ?
C9A C10A N1A 117.6(5) . . ?
C10A C11A C12A 118.0(5) . . ?
C11A C12A C7A 120.6(5) . . ?
C1A C13A C14A 122.1(5) . . ?
C1A C13A C22A 129.4(5) . . ?
C14A C13A C22A 108.5(4) . . ?
C15A C14A C13A 110.7(5) . . ?
C14A C15A C16A 107.9(5) . . ?
C14A C15A C27A 127.0(5) . . ?
C16A C15A C27A 125.1(4) . . ?
C17A C16A C15A 123.2(5) . . ?
C17A C16A C22A 129.3(5) . . ?
C15A C16A C22A 107.4(4) . . ?
C16A C17A C18A 131.2(5) . . ?
C19A C18A C17A 123.7(5) . . ?
C19A C18A C24A 117.6(5) . . ?
C17A C18A C24A 118.6(5) . . ?
C20A C19A C18A 130.9(5) . . ?
C19A C20A C21A 133.1(5) . . ?
C22A C21A C20A 124.8(5) . . ?
C22A C21A C23A 119.3(5) . . ?
C20A C21A C23A 115.8(5) . . ?
C21A C22A C13A 128.2(5) . . ?
C21A C22A C16A 126.4(5) . . ?
C13A C22A C16A 105.4(4) . . ?
C18A C24A C26A 109.4(4) . . ?
C18A C24A C25A 115.8(4) . . ?
C26A C24A C25A 110.8(5) . . ?
O2B N1B O1B 123.7(5) . . ?
O2B N1B C10B 118.9(5) . . ?
O1B N1B C10B 117.4(5) . . ?
C1B C2B C3B 173.9(9) . . ?
C1C C2B C3B 167.5(13) . . ?
C4B C3B C2B 178.1(6) . . ?
C3B C4B C5B 178.8(6) . . ?
C6B C5B C4B 178.5(6) . . ?
C5B C6B C7B 177.5(6) . . ?
C12B C7B C8B 119.5(4) . . ?
C12B C7B C6B 121.2(5) . . ?
C8B C7B C6B 119.3(5) . . ?
C9B C8B C7B 121.2(5) . . ?
C8B C9B C10B 118.1(5) . . ?
C9B C10B C11B 123.4(4) . . ?
C9B C10B N1B 119.6(5) . . ?
C11B C10B N1B 117.0(5) . . ?
C12B C11B C10B 117.2(5) . . ?
C7B C12B C11B 120.7(5) . . ?
C2B C1B C13B 172.6(14) . . ?
C1B C13B C14B 118.4(10) . . ?
C1B C13B C22B 132.8(10) . . ?
C14B C13B C22B 108.7(9) . . ?
C15B C14B C13B 111.4(12) . . ?
C14B C15B C16B 107.3(10) . . ?
C14B C15B C27B 126.6(11) . . ?
C16B C15B C27B 126.1(9) . . ?
C17B C16B C15B 121.3(9) . . ?
C17B C16B C22B 130.1(10) . . ?
C15B C16B C22B 108.5(9) . . ?
C16B C17B C18B 128.5(11) . . ?
C19B C18B C17B 124.5(11) . . ?
C19B C18B C24B 127.8(11) . . ?
C17B C18B C24B 107.6(12) . . ?
C18B C19B C20B 132.8(11) . . ?
C21B C20B C19B 132.2(11) . . ?
C20B C21B C22B 124.4(9) . . ?
C20B C21B C23B 118.9(11) . . ?
C22B C21B C23B 116.6(11) . . ?
C21B C22B C13B 128.6(10) . . ?
C21B C22B C16B 127.4(10) . . ?
C13B C22B C16B 104.0(9) . . ?
C25B C24B C26B 123.7(10) . . ?
C25B C24B C18B 109.6(9) . . ?
C26B C24B C18B 114.1(9) . . ?
C2B C1C C13C 173(3) . . ?
C22C C13C C14C 108.9(17) . . ?
C22C C13C C1C 132.9(19) . . ?
C14C C13C C1C 118.2(18) . . ?
C15C C14C C13C 111.0(19) . . ?
C16C C15C C14C 107(2) . . ?
C16C C15C C27C 129(2) . . ?
C14C C15C C27C 124.4(19) . . ?
C17C C16C C15C 123.2(19) . . ?
C17C C16C C22C 125.6(17) . . ?
C15C C16C C22C 111.2(18) . . ?
C18C C17C C16C 135(2) . . ?
C17C C18C C19C 125.9(19) . . ?
C17C C18C C24C 128(2) . . ?
C19C C18C C24C 106.4(15) . . ?
C20C C19C C18C 128.5(16) . . ?
C19C C20C C21C 129.5(19) . . ?
C22C C21C C20C 130(2) . . ?
C22C C21C C23C 114(2) . . ?
C20C C21C C23C 115.6(19) . . ?
C21C C22C C13C 133(2) . . ?
C21C C22C C16C 125(2) . . ?
C13C C22C C16C 102.1(16) . . ?
C26C C24C C18C 105.3(18) . . ?
C26C C24C C25C 100.4(18) . . ?
C18C C24C C25C 108.7(17) . . ?

_refine_diff_density_max         1.029
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.076

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5bg
_database_code_depnum_ccdc_archive 'CCDC 1970440'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT340_5bg                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01445 Ang.  
RESPONSE: 'Low quality of crystals'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        
1-(4-(5-(5-isopropyl-3,8-dimethylazulen-1-yl)thiophen-2-yl)phenyl)ethan-1-one
_chemical_formula_moiety         'C27 H26 O S'
_chemical_formula_sum            'C27 H26 O S'
_chemical_formula_weight         398.54
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   23.690(5)
_cell_length_b                   16.013(3)
_cell_length_c                   5.510(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2090.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    701
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      65.7200
_cell_measurement_theta_min      2.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.1344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7893
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.085
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_ 1 omega -32.00 71.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - 42.6143 -37.0000 -60.0000 103 #__ type_ start__ end____ width___ exp.time_ 2 omega 73.00 98.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - 42.6143 125.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega 15.00 118.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - 42.6143 37.0000 -120.0000 103 #__ type_ start__ end____ width___ exp.time_ 4 omega 39.00 73.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 5 omega 44.00 74.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 6 omega 44.00 70.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega 39.00 64.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 8 omega 84.00 176.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 61.0000 82.0000 92 #__ type_ start__ end____ width___ exp.time_ 9 omega 40.00 77.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 0.0000 37 #__ type_ start__ end____ width___ exp.time_ 10 omega 43.00 75.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -60.0000 32 #__ type_ start__ end____ width___ exp.time_ 11 omega 50.00 79.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 179.0000 -180.0000 29 #__ type_ start__ end____ width___ exp.time_ 12 omega 106.00 148.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 179.0000 -180.0000 42 #__ type_ start__ end____ width___ exp.time_ 13 omega 45.00 75.00 1.0000 400.0000 omega____ theta____ kappa____ phi______ fra
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0421144000
_diffrn_orient_matrix_UB_12      0.0283249000
_diffrn_orient_matrix_UB_13      0.1962322000
_diffrn_orient_matrix_UB_21      0.0357288000
_diffrn_orient_matrix_UB_22      -0.0788866000
_diffrn_orient_matrix_UB_23      -0.0453564000
_diffrn_orient_matrix_UB_31      0.0343662000
_diffrn_orient_matrix_UB_32      0.0473708000
_diffrn_orient_matrix_UB_33      -0.1934864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.619
_reflns_Friedel_fraction_max     0.565
_reflns_number_gt                2246
_reflns_number_total             3521
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.96
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.1022
_refine_ls_restrained_S_all      1.072
_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)+(0.1448P)²+0.6984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2529
_refine_ls_wR_factor_ref         0.3156
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C19(H19), C20(H20),
 C22(H22), C2(H2)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.64250(8) 0.14463(14) 0.9485(5) 0.0385(6) Uani 1 1 d . . . . .
C1 C 0.6619(4) 0.0597(6) 0.776(2) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.6953(4) 0.1741(7) 0.561(2) 0.040(2) Uani 1 1 d . . . . .
H3 H 0.713442 0.201664 0.429663 0.048 Uiso 1 1 calc R . . . .
C4 C 0.6724(3) 0.2156(6) 0.750(2) 0.039(2) Uani 1 1 d . . . . .
C6 C 0.6472(3) 0.3365(6) 1.0117(19) 0.036(2) Uani 1 1 d . . . . .
H6 H 0.630771 0.299113 1.125327 0.044 Uiso 1 1 calc R . . . .
C7 C 0.6469(3) 0.4212(6) 1.060(2) 0.038(2) Uani 1 1 d . . . . .
H7 H 0.631089 0.441120 1.207905 0.046 Uiso 1 1 calc R . . . .
C9 C 0.6929(3) 0.4480(6) 0.683(2) 0.035(2) Uani 1 1 d . . . . .
H9 H 0.708320 0.485916 0.568053 0.042 Uiso 1 1 calc R . . . .
C10 C 0.6939(3) 0.3631(6) 0.6365(19) 0.033(2) Uani 1 1 d . . . . .
H10 H 0.710632 0.343813 0.490030 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6709(3) 0.5699(5) 0.959(2) 0.0351(19) Uani 1 1 d . . . . .
C12 C 0.6904(4) 0.6318(6) 0.771(2) 0.041(2) Uani 1 1 d . . . . .
H12A H 0.685242 0.688623 0.832534 0.062 Uiso 1 1 calc GR . . . .
H12B H 0.668148 0.624599 0.621993 0.062 Uiso 1 1 calc GR . . . .
H12C H 0.730386 0.622330 0.734729 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.6514(3) -0.0245(6) 0.867(2) 0.037(2) Uani 1 1 d . . . . .
C14 C 0.6847(3) -0.0606(6) 1.057(2) 0.036(2) Uani 1 1 d . . . . .
H14 H 0.717030 -0.034935 1.126977 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6637(4) -0.1373(6) 1.126(2) 0.037(2) Uani 1 1 d . . . . .
C16 C 0.6165(3) -0.1550(6) 0.978(2) 0.035(2) Uani 1 1 d . . . . .
C17 C 0.6076(3) -0.0836(6) 0.8098(18) 0.0317(19) Uani 1 1 d . . . . .
C18 C 0.5651(4) -0.0765(7) 0.633(2) 0.043(2) Uani 1 1 d . . . . .
C19 C 0.5245(4) -0.1397(7) 0.583(2) 0.045(3) Uani 1 1 d . . . . .
H19 H 0.498846 -0.125295 0.457263 0.054 Uiso 1 1 calc R . . . .
C20 C 0.5149(4) -0.2173(7) 0.680(3) 0.050(3) Uani 1 1 d . . . . .
H20 H 0.485224 -0.247346 0.604141 0.060 Uiso 1 1 calc R . . . .
C21 C 0.5409(4) -0.2605(6) 0.872(2) 0.039(2) Uani 1 1 d . . . . .
C22 C 0.5868(3) -0.2293(6) 1.0003(18) 0.035(2) Uani 1 1 d . . . . .
H22 H 0.600163 -0.265061 1.125316 0.042 Uiso 1 1 calc R . . . .
C23 C 0.5606(4) 0.0003(6) 0.478(2) 0.043(2) Uani 1 1 d . . . . .
H23A H 0.564928 0.050057 0.579886 0.064 Uiso 1 1 calc GR . . . .
H23B H 0.523655 0.001486 0.398395 0.064 Uiso 1 1 calc GR . . . .
H23C H 0.590421 -0.000449 0.354517 0.064 Uiso 1 1 calc GR . . . .
C24 C 0.5181(3) -0.3464(6) 0.941(3) 0.043(2) Uani 1 1 d . . . . .
H24 H 0.543923 -0.369651 1.067307 0.052 Uiso 1 1 calc R . . . .
C25 C 0.4603(4) -0.3387(7) 1.056(3) 0.048(3) Uani 1 1 d . . . . .
H25A H 0.462359 -0.300733 1.195276 0.072 Uiso 1 1 calc GR . . . .
H25B H 0.447571 -0.393835 1.111000 0.072 Uiso 1 1 calc GR . . . .
H25C H 0.433460 -0.316626 0.936868 0.072 Uiso 1 1 calc GR . . . .
C26 C 0.5176(4) -0.4072(8) 0.736(3) 0.057(3) Uani 1 1 d . . . . .
H26A H 0.491799 -0.387530 0.609066 0.086 Uiso 1 1 calc GR . . . .
H26B H 0.505023 -0.461869 0.794658 0.086 Uiso 1 1 calc GR . . . .
H26C H 0.555781 -0.412257 0.668400 0.086 Uiso 1 1 calc GR . . . .
C27 C 0.6887(4) -0.1902(7) 1.320(2) 0.042(2) Uani 1 1 d . . . . .
H27A H 0.726653 -0.169864 1.359515 0.063 Uiso 1 1 calc GR . . . .
H27B H 0.691042 -0.248191 1.264136 0.063 Uiso 1 1 calc GR . . . .
H27C H 0.664916 -0.187502 1.465694 0.063 Uiso 1 1 calc GR . . . .
C2 C 0.6899(4) 0.0875(7) 0.574(2) 0.044(2) Uani 1 1 d . . . . .
H2 H 0.704361 0.050977 0.452881 0.053 Uiso 1 1 calc R . . . .
O1 O 0.6561(3) 0.5918(5) 1.1594(15) 0.0438(17) Uani 1 1 d . . . . .
C5 C 0.6712(3) 0.3046(6) 0.7981(19) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.6697(3) 0.4778(6) 0.8935(19) 0.035(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 C1 1.721(11) . ?
S1 C4 1.728(11) . ?
C1 C13 1.461(13) . ?
C1 C2 1.373(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.350(16) . ?
C3 C2 1.394(14) . ?
C4 C5 1.450(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(14) . ?
C6 C5 1.404(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.399(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(13) . ?
C9 C8 1.370(14) . ?
C10 H10 0.9500 . ?
C10 C5 1.399(14) . ?
C11 C12 1.505(15) . ?
C11 O1 1.213(14) . ?
C11 C8 1.519(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.433(14) . ?
C13 C17 1.438(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(14) . ?
C15 C16 1.414(14) . ?
C15 C27 1.489(15) . ?
C16 C17 1.485(14) . ?
C16 C22 1.388(13) . ?
C17 C18 1.406(14) . ?
C18 C19 1.424(14) . ?
C18 C23 1.501(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.405(17) . ?
C21 C22 1.389(14) . ?
C21 C24 1.526(14) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 1.0000 . ?
C24 C25 1.515(15) . ?
C24 C26 1.491(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C2 H2 0.9500 . ?

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
C1 S1 C4 93.5(5) . . ?
C13 C1 S1 119.7(9) . . ?
C2 C1 S1 108.8(8) . . ?
C2 C1 C13 131.4(10) . . ?
C4 C3 H3 122.8 . . ?
C4 C3 C2 114.4(10) . . ?
C2 C3 H3 122.8 . . ?
C3 C4 S1 109.3(8) . . ?
C3 C4 C5 129.2(10) . . ?
C5 C4 S1 121.6(8) . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.5(10) . . ?
C5 C6 H6 119.3 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(10) . . ?
C8 C7 H7 119.8 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(9) . . ?
C9 C10 H10 118.9 . . ?
C9 C10 C5 122.2(9) . . ?
C5 C10 H10 118.9 . . ?
C12 C11 C8 118.9(10) . . ?
O1 C11 C12 121.8(9) . . ?
O1 C11 C8 119.3(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C1 121.9(8) . . ?
C14 C13 C17 107.0(8) . . ?
C17 C13 C1 130.9(9) . . ?
C13 C14 H14 124.4 . . ?
C15 C14 C13 111.1(8) . . ?
C15 C14 H14 124.4 . . ?
C14 C15 C16 107.8(9) . . ?
C14 C15 C27 124.1(9) . . ?
C16 C15 C27 128.1(9) . . ?
C15 C16 C17 108.5(8) . . ?
C22 C16 C15 121.4(9) . . ?
C22 C16 C17 130.1(9) . . ?
C13 C17 C16 105.5(8) . . ?
C18 C17 C13 128.0(9) . . ?
C18 C17 C16 126.5(9) . . ?
C17 C18 C19 124.1(10) . . ?
C17 C18 C23 120.7(9) . . ?
C19 C18 C23 115.2(9) . . ?
C18 C19 H19 113.6 . . ?
C20 C19 C18 132.9(11) . . ?
C20 C19 H19 113.6 . . ?
C19 C20 H20 114.1 . . ?
C19 C20 C21 131.9(11) . . ?
C21 C20 H20 114.1 . . ?
C20 C21 C24 118.3(10) . . ?
C22 C21 C20 123.3(10) . . ?
C22 C21 C24 118.4(10) . . ?
C16 C22 C21 131.2(10) . . ?
C16 C22 H22 114.4 . . ?
C21 C22 H22 114.4 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24 106.9 . . ?
C25 C24 C21 110.5(8) . . ?
C25 C24 H24 106.9 . . ?
C26 C24 C21 113.8(12) . . ?
C26 C24 H24 106.9 . . ?
C26 C24 C25 111.4(8) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 C27 H27A 109.5 . . ?
C15 C27 H27B 109.5 . . ?
C15 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1 C2 C3 114.1(10) . . ?
C1 C2 H2 123.0 . . ?
C3 C2 H2 123.0 . . ?
C6 C5 C4 121.2(9) . . ?
C10 C5 C4 122.3(10) . . ?
C10 C5 C6 116.5(9) . . ?
C7 C8 C11 118.8(9) . . ?
C9 C8 C7 119.1(9) . . ?
C9 C8 C11 122.0(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3bk
_database_code_depnum_ccdc_archive 'CCDC 1970441'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-((5-isopropyl-3,8-dimethylazulen-1-yl)octa-1,3,5,7-tetrayn-1-yl)benzonitrile
_chemical_formula_moiety         'C30 H21 N'
_chemical_formula_sum            'C30 H21 N'
_chemical_formula_weight         395.48
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.594(3)
_cell_length_b                   10.028(3)
_cell_length_c                   15.437(3)
_cell_angle_alpha                99.94(2)
_cell_angle_beta                 95.43(2)
_cell_angle_gamma                109.53(2)
_cell_volume                     1076.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    726
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.0280
_cell_measurement_theta_min      2.3160
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.1901
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6596
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.208
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  96.00   1.00  250.00    --   15.58  77.00 -90.00  102
  2  ω     -6.00  98.00   1.00  250.00    --   15.58  77.00  30.00  104
  3  ω    -56.00  35.00   1.00  250.00    --  -16.44  77.00 150.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291989000
_diffrn_orient_matrix_UB_12      -0.0273530000
_diffrn_orient_matrix_UB_13      0.0359930000
_diffrn_orient_matrix_UB_21      -0.0959679000
_diffrn_orient_matrix_UB_22      -0.0405540000
_diffrn_orient_matrix_UB_23      0.0010475000
_diffrn_orient_matrix_UB_31      0.0055789000
_diffrn_orient_matrix_UB_32      -0.0593249000
_diffrn_orient_matrix_UB_33      -0.0306511000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1724
_reflns_number_total             4220
_reflns_odcompleteness_completeness 85.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.71
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.0739
_refine_ls_restrained_S_all      0.993
_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)+(0.0333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1762
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C22(H22), C17(H17), C14(H14), C10(H10), C13(H13), C23(H23), C11(H11)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 1.7360(5) 1.6138(4) 0.8230(3) 0.0468(11) Uani 1 1 d . . . . .
C9 C 1.2821(5) 1.0681(4) 0.6705(3) 0.0257(10) Uani 1 1 d . . . . .
C19 C -0.0638(5) -0.2336(4) 0.1672(3) 0.0273(10) Uani 1 1 d . . . . .
C5 C 0.8022(5) 0.5537(4) 0.5131(3) 0.0299(11) Uani 1 1 d . . . . .
C27 C -0.1975(5) -0.1341(4) 0.0395(3) 0.0329(11) Uani 1 1 d . . . . .
H27A H -0.178864 -0.202461 -0.009068 0.049 Uiso 1 1 calc GR . . . .
H27B H -0.167609 -0.039120 0.024075 0.049 Uiso 1 1 calc GR . . . .
H27C H -0.329625 -0.169779 0.048852 0.049 Uiso 1 1 calc GR . . . .
C25 C -0.1735(5) -0.3794(4) 0.1298(3) 0.0298(11) Uani 1 1 d . . . . .
H25 H -0.251576 -0.396269 0.074199 0.036 Uiso 1 1 calc R . . . .
C7 C 1.0428(5) 0.8029(4) 0.5981(3) 0.0284(10) Uani 1 1 d . . . . .
C22 C 0.0256(5) -0.3897(4) 0.3115(3) 0.0330(11) Uani 1 1 d . . . . .
H22 H 0.059750 -0.419541 0.363752 0.040 Uiso 1 1 calc R . . . .
C6 C 0.9147(5) 0.6687(4) 0.5547(3) 0.0275(10) Uani 1 1 d . . . . .
C16 C 0.1536(5) -0.0191(4) 0.2519(3) 0.0290(11) Uani 1 1 d . . . . .
C17 C 0.0628(5) 0.0075(4) 0.1743(3) 0.0296(11) Uani 1 1 d . . . . .
H17 H 0.089978 0.099960 0.159989 0.036 Uiso 1 1 calc R . . . .
C1 C 0.2966(5) 0.0938(4) 0.3144(3) 0.0297(11) Uani 1 1 d . . . . .
C2 C 0.4179(5) 0.1989(4) 0.3618(3) 0.0302(11) Uani 1 1 d . . . . .
C18 C -0.0700(5) -0.1204(4) 0.1231(3) 0.0276(10) Uani 1 1 d . . . . .
C20 C 0.0727(5) -0.1694(4) 0.2507(3) 0.0285(10) Uani 1 1 d . . . . .
C26 C 0.2400(5) -0.1516(4) 0.4026(3) 0.0347(11) Uani 1 1 d . . . . .
H26A H 0.193443 -0.077070 0.430220 0.052 Uiso 1 1 calc GR . . . .
H26B H 0.367138 -0.105227 0.389421 0.052 Uiso 1 1 calc GR . . . .
H26C H 0.244886 -0.215230 0.443660 0.052 Uiso 1 1 calc GR . . . .
C3 C 0.5533(5) 0.3180(4) 0.4166(3) 0.0290(10) Uani 1 1 d . . . . .
C14 C 1.2842(5) 1.1794(4) 0.6261(3) 0.0313(11) Uani 1 1 d . . . . .
H14 H 1.203618 1.159266 0.570815 0.038 Uiso 1 1 calc R . . . .
C4 C 0.6713(5) 0.4262(4) 0.4636(3) 0.0289(10) Uani 1 1 d . . . . .
C24 C -0.1851(5) -0.5048(4) 0.1624(3) 0.0310(11) Uani 1 1 d . . . . .
C10 C 1.4012(5) 1.0977(4) 0.7506(3) 0.0297(10) Uani 1 1 d . . . . .
H10 H 1.400654 1.021071 0.779354 0.036 Uiso 1 1 calc R . . . .
C13 C 1.4072(5) 1.3202(4) 0.6648(3) 0.0301(11) Uani 1 1 d . . . . .
H13 H 1.412092 1.396508 0.635075 0.036 Uiso 1 1 calc R . . . .
C8 C 1.1525(5) 0.9226(4) 0.6318(3) 0.0297(11) Uani 1 1 d . . . . .
C21 C 0.1090(5) -0.2394(4) 0.3179(3) 0.0302(11) Uani 1 1 d . . . . .
C23 C -0.0967(5) -0.5038(4) 0.2445(3) 0.0327(11) Uani 1 1 d . . . . .
H23 H -0.123533 -0.596892 0.257923 0.039 Uiso 1 1 calc R . . . .
C15 C 1.6429(5) 1.4981(4) 0.7879(3) 0.0342(11) Uani 1 1 d . . . . .
C12 C 1.5217(5) 1.3497(4) 0.7458(3) 0.0290(11) Uani 1 1 d . . . . .
C28 C -0.3041(5) -0.6492(4) 0.0977(3) 0.0328(11) Uani 1 1 d . . . . .
H28 H -0.417097 -0.636123 0.066847 0.039 Uiso 1 1 calc R . . . .
C11 C 1.5228(5) 1.2400(4) 0.7897(3) 0.0302(11) Uani 1 1 d . . . . .
H11 H 1.604051 1.260877 0.844852 0.036 Uiso 1 1 calc R . . . .
C29 C -0.3762(6) -0.7777(4) 0.1430(3) 0.0443(13) Uani 1 1 d . . . . .
H29A H -0.269277 -0.803014 0.165565 0.066 Uiso 1 1 calc GR . . . .
H29B H -0.467600 -0.861119 0.099678 0.066 Uiso 1 1 calc GR . . . .
H29C H -0.437755 -0.750760 0.192715 0.066 Uiso 1 1 calc GR . . . .
C30 C -0.1889(6) -0.6848(4) 0.0263(3) 0.0422(12) Uani 1 1 d . . . . .
H30A H -0.155007 -0.607403 -0.006905 0.063 Uiso 1 1 calc GR . . . .
H30B H -0.264988 -0.776872 -0.014778 0.063 Uiso 1 1 calc GR . . . .
H30C H -0.073312 -0.692851 0.055084 0.063 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N1 C15 1.141(4) . ?
C9 C14 1.404(5) . ?
C9 C10 1.385(5) . ?
C9 C8 1.443(5) . ?
C19 C25 1.403(5) . ?
C19 C18 1.432(5) . ?
C19 C20 1.472(5) . ?
C5 C6 1.206(5) . ?
C5 C4 1.370(5) . ?
C27 C18 1.494(5) . ?
C25 C24 1.413(5) . ?
C7 C6 1.376(5) . ?
C7 C8 1.200(5) . ?
C22 C21 1.409(5) . ?
C22 C23 1.393(5) . ?
C16 C17 1.435(5) . ?
C16 C1 1.412(5) . ?
C16 C20 1.421(5) . ?
C17 C18 1.386(5) . ?
C1 C2 1.205(5) . ?
C2 C3 1.366(5) . ?
C20 C21 1.403(5) . ?
C26 C21 1.499(5) . ?
C3 C4 1.209(5) . ?
C14 C13 1.394(5) . ?
C24 C23 1.374(5) . ?
C24 C28 1.538(5) . ?
C10 C11 1.403(5) . ?
C13 C12 1.379(5) . ?
C15 C12 1.457(5) . ?
C12 C11 1.390(5) . ?
C28 C29 1.536(5) . ?
C28 C30 1.537(5) . ?

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
C14 C9 C8 118.9(4) . . ?
C10 C9 C14 120.5(3) . . ?
C10 C9 C8 120.5(4) . . ?
C25 C19 C18 121.4(4) . . ?
C25 C19 C20 129.6(4) . . ?
C18 C19 C20 108.9(3) . . ?
C6 C5 C4 177.5(5) . . ?
C19 C25 C24 129.6(4) . . ?
C8 C7 C6 176.4(5) . . ?
C23 C22 C21 133.3(4) . . ?
C5 C6 C7 176.9(5) . . ?
C1 C16 C17 121.6(4) . . ?
C1 C16 C20 130.4(4) . . ?
C20 C16 C17 108.0(3) . . ?
C18 C17 C16 110.6(3) . . ?
C2 C1 C16 173.5(4) . . ?
C1 C2 C3 179.0(5) . . ?
C19 C18 C27 127.5(3) . . ?
C17 C18 C19 106.7(4) . . ?
C17 C18 C27 125.8(4) . . ?
C16 C20 C19 105.6(3) . . ?
C21 C20 C19 127.6(3) . . ?
C21 C20 C16 126.7(4) . . ?
C4 C3 C2 177.9(5) . . ?
C13 C14 C9 118.6(4) . . ?
C3 C4 C5 176.4(5) . . ?
C25 C24 C28 115.0(4) . . ?
C23 C24 C25 124.6(4) . . ?
C23 C24 C28 120.4(4) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C13 C14 120.6(4) . . ?
C7 C8 C9 178.4(5) . . ?
C22 C21 C26 116.9(4) . . ?
C20 C21 C22 123.6(4) . . ?
C20 C21 C26 119.5(3) . . ?
C24 C23 C22 131.0(4) . . ?
N1 C15 C12 178.1(5) . . ?
C13 C12 C15 120.3(4) . . ?
C13 C12 C11 121.2(4) . . ?
C11 C12 C15 118.5(4) . . ?
C29 C28 C24 114.2(3) . . ?
C29 C28 C30 109.7(3) . . ?
C30 C28 C24 109.6(3) . . ?
C12 C11 C10 118.5(4) . . ?

_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ce
_database_code_depnum_ccdc_archive 'CCDC 1970439'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
5-(4,8-dimethyl-6-phenylazulen-1-yl)-1-phenylpenta-2,4-diyn-1-one
_chemical_formula_moiety         'C29 H20 O'
_chemical_formula_sum            'C29 H20 O'
_chemical_formula_weight         384.45
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   6.921(3)
_cell_length_b                   12.804(3)
_cell_length_c                   22.410(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.585(4)
_cell_angle_gamma                90
_cell_volume                     1979.53(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.2953
_cell_measurement_theta_min      2.9468
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_preparation       .
_exptl_crystal_recrystallization_method .
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_unetI/netI     0.0990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12799
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.020
_diffrn_ambient_temperature      100
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'KUMA KM4 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_special_details          .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2298
_reflns_number_total             3883
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.032
_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)+(0.0661P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1759
_refine_special_details          .
_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:
 C14(H14), C18(H18), C7(H7), C10(H10), C25(H25), C28(H28), C27(H27), C20(H20),
 C11(H11), C26(H26), C8(H8), C29(H29), C13(H13), C9(H9)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.3029(3) 0.42370(15) 0.20109(9) 0.0319(6) Uani 1 1 d . . . . .
C14 C 0.1684(4) 0.6836(2) -0.19817(13) 0.0247(7) Uani 1 1 d . . . . .
H14 H 0.157350 0.667202 -0.239649 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1657(4) 0.9598(2) -0.07599(12) 0.0223(7) Uani 1 1 d . . . . .
H18 H 0.174031 1.002152 -0.041060 0.027 Uiso 1 1 calc R . . . .
C12 C 0.2069(4) 0.6641(2) -0.09628(13) 0.0215(7) Uani 1 1 d . . . . .
C6 C 0.3281(4) 0.2658(2) 0.14627(12) 0.0219(7) Uani 1 1 d . . . . .
C19 C 0.1377(4) 1.0161(2) -0.12942(12) 0.0200(7) Uani 1 1 d . . . . .
C7 C 0.3569(4) 0.2051(2) 0.19796(13) 0.0260(7) Uani 1 1 d . . . . .
H7 H 0.363073 0.237689 0.236153 0.031 Uiso 1 1 calc R . . . .
C24 C 0.1241(4) 1.1318(2) -0.12183(12) 0.0226(7) Uani 1 1 d . . . . .
C1 C 0.2358(4) 0.6097(2) -0.04162(13) 0.0235(7) Uani 1 1 d . . . . .
C10 C 0.3388(4) 0.1103(2) 0.08709(14) 0.0303(8) Uani 1 1 d . . . . .
H10 H 0.332959 0.077458 0.048977 0.036 Uiso 1 1 calc R . . . .
C17 C 0.1838(4) 0.8531(2) -0.06440(12) 0.0219(7) Uani 1 1 d . . . . .
C4 C 0.2915(4) 0.4406(2) 0.09755(13) 0.0261(7) Uani 1 1 d . . . . .
C25 C 0.2655(4) 1.1855(2) -0.08514(13) 0.0238(7) Uani 1 1 d . . . . .
H25 H 0.374289 1.148552 -0.067307 0.029 Uiso 1 1 calc R . . . .
C28 C -0.0509(4) 1.2945(2) -0.13663(12) 0.0243(7) Uani 1 1 d . . . . .
H28 H -0.159921 1.331840 -0.154027 0.029 Uiso 1 1 calc R . . . .
C22 C 0.0914(5) 0.8599(2) -0.27536(12) 0.0289(8) Uani 1 1 d . . . . .
H22A H 0.048190 0.925824 -0.294274 0.043 Uiso 1 1 calc GR . . . .
H22B H -0.007081 0.806014 -0.284505 0.043 Uiso 1 1 calc GR . . . .
H22C H 0.213771 0.838296 -0.290762 0.043 Uiso 1 1 calc GR . . . .
C27 C 0.0878(4) 1.3462(2) -0.09966(13) 0.0253(7) Uani 1 1 d . . . . .
H27 H 0.073281 1.418418 -0.091457 0.030 Uiso 1 1 calc R . . . .
C2 C 0.2580(4) 0.5550(2) 0.00254(13) 0.0259(7) Uani 1 1 d . . . . .
C21 C 0.1210(4) 0.8749(2) -0.20829(12) 0.0212(7) Uani 1 1 d . . . . .
C20 C 0.1141(4) 0.9774(2) -0.18770(12) 0.0221(7) Uani 1 1 d . . . . .
H20 H 0.089735 1.028746 -0.217982 0.027 Uiso 1 1 calc R . . . .
C11 C 0.3190(4) 0.2170(2) 0.09054(13) 0.0261(7) Uani 1 1 d . . . . .
H11 H 0.299202 0.257309 0.054993 0.031 Uiso 1 1 calc R . . . .
C16 C 0.1827(4) 0.7739(2) -0.10751(12) 0.0202(7) Uani 1 1 d . . . . .
C26 C 0.2482(5) 1.2920(2) -0.07464(13) 0.0264(7) Uani 1 1 d . . . . .
H26 H 0.345905 1.327588 -0.050376 0.032 Uiso 1 1 calc R . . . .
C8 C 0.3765(4) 0.0983(2) 0.19401(14) 0.0308(8) Uani 1 1 d . . . . .
H8 H 0.396468 0.057581 0.229408 0.037 Uiso 1 1 calc R . . . .
C23 C 0.2054(5) 0.8239(2) 0.00077(13) 0.0290(8) Uani 1 1 d . . . . .
H23A H 0.203892 0.887308 0.025249 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.328551 0.787121 0.009616 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.097976 0.778354 0.009943 0.044 Uiso 1 1 calc GR . . . .
C29 C -0.0322(4) 1.1885(2) -0.14854(12) 0.0241(7) Uani 1 1 d . . . . .
H29 H -0.126261 1.154519 -0.174974 0.029 Uiso 1 1 calc R . . . .
C15 C 0.1554(4) 0.7850(2) -0.17358(13) 0.0212(7) Uani 1 1 d . . . . .
C13 C 0.1997(4) 0.6129(2) -0.15239(13) 0.0258(7) Uani 1 1 d . . . . .
H13 H 0.214372 0.539737 -0.157631 0.031 Uiso 1 1 calc R . . . .
C9 C 0.3672(4) 0.0501(2) 0.13841(14) 0.0308(8) Uani 1 1 d . . . . .
H9 H 0.380144 -0.023541 0.135552 0.037 Uiso 1 1 calc R . . . .
C3 C 0.2782(4) 0.4945(2) 0.05311(13) 0.0250(7) Uani 1 1 d . . . . .
C5 C 0.3077(4) 0.3802(2) 0.15208(13) 0.0233(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 1.234(3) . ?
C14 C15 1.416(4) . ?
C14 C13 1.373(4) . ?
C18 C19 1.398(4) . ?
C18 C17 1.395(4) . ?
C12 C1 1.410(4) . ?
C12 C16 1.436(4) . ?
C12 C13 1.416(4) . ?
C6 C7 1.396(4) . ?
C6 C11 1.393(4) . ?
C6 C5 1.479(4) . ?
C19 C24 1.495(4) . ?
C19 C20 1.394(4) . ?
C7 C8 1.378(4) . ?
C24 C25 1.407(4) . ?
C24 C29 1.397(4) . ?
C1 C2 1.212(4) . ?
C10 C11 1.375(4) . ?
C10 C9 1.385(4) . ?
C17 C16 1.400(4) . ?
C17 C23 1.503(4) . ?
C4 C3 1.209(4) . ?
C4 C5 1.443(4) . ?
C25 C26 1.390(4) . ?
C28 C27 1.385(4) . ?
C28 C29 1.391(4) . ?
C22 C21 1.513(4) . ?
C27 C26 1.389(4) . ?
C2 C3 1.371(4) . ?
C21 C20 1.394(4) . ?
C21 C15 1.398(4) . ?
C16 C15 1.484(4) . ?
C8 C9 1.387(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
C13 C14 C15 109.0(3) . . ?
C17 C18 C19 132.0(3) . . ?
C1 C12 C16 130.0(3) . . ?
C1 C12 C13 122.3(3) . . ?
C13 C12 C16 107.6(2) . . ?
C7 C6 C5 119.1(3) . . ?
C11 C6 C7 119.2(3) . . ?
C11 C6 C5 121.7(3) . . ?
C18 C19 C24 114.8(2) . . ?
C20 C19 C18 128.1(3) . . ?
C20 C19 C24 117.1(2) . . ?
C8 C7 C6 120.5(3) . . ?
C25 C24 C19 120.2(3) . . ?
C29 C24 C19 121.3(3) . . ?
C29 C24 C25 118.4(3) . . ?
C2 C1 C12 174.3(3) . . ?
C11 C10 C9 120.9(3) . . ?
C18 C17 C16 125.9(3) . . ?
C18 C17 C23 115.1(2) . . ?
C16 C17 C23 119.0(2) . . ?
C3 C4 C5 177.6(3) . . ?
C26 C25 C24 120.9(3) . . ?
C27 C28 C29 120.7(3) . . ?
C28 C27 C26 119.7(3) . . ?
C1 C2 C3 178.2(3) . . ?
C20 C21 C22 116.3(2) . . ?
C20 C21 C15 126.8(3) . . ?
C15 C21 C22 116.9(2) . . ?
C21 C20 C19 129.8(3) . . ?
C10 C11 C6 119.9(3) . . ?
C12 C16 C15 105.8(2) . . ?
C17 C16 C12 126.4(3) . . ?
C17 C16 C15 127.7(2) . . ?
C27 C26 C25 119.9(3) . . ?
C7 C8 C9 120.1(3) . . ?
C28 C29 C24 120.4(3) . . ?
C14 C15 C16 107.0(2) . . ?
C21 C15 C14 123.4(3) . . ?
C21 C15 C16 129.5(3) . . ?
C14 C13 C12 110.5(3) . . ?
C10 C9 C8 119.4(3) . . ?
C4 C3 C2 178.5(3) . . ?
O1 C5 C6 122.3(3) . . ?
O1 C5 C4 120.4(3) . . ?
C4 C5 C6 117.3(3) . . ?

_olex2_exptl_crystal_mounting_method .
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ae
_database_code_depnum_ccdc_archive 'CCDC 1970435'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;

_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        5-(azulen-1-yl)-1-phenylpenta-2,4-diyn-1-one
_chemical_formula_moiety         'C21 H12 O'
_chemical_formula_sum            'C21 H12 O'
_chemical_formula_weight         280.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.413(3)
_cell_length_b                   3.830(3)
_cell_length_c                   21.881(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.59(2)
_cell_angle_gamma                90
_cell_volume                     1383.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    846
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.4150
_cell_measurement_theta_min      2.6310
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 0 31 0.0209
-20 -3 -1 0.1097
-7 0 31 0.0105
21 3 -2 0.1377
7 0 -31 0.0123

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.0067 0.0095 31.0094 -0.9680 0.2426 -0.1247
-20.2109 -2.5919 -0.7707 -0.1004 0.0275 0.9946
-6.6522 0.0226 30.7968 -0.9490 0.2631 -0.1737
20.8873 2.5953 -2.1573 0.1909 -0.0526 -0.9802
7.1323 0.0377 -30.8208 0.9526 -0.2641 0.1507

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7817
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.958
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.9825
_diffrn_measured_fraction_theta_max 0.8849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  15.00   1.00  100.00    --  -21.12 -37.00-180.00  121
  2  ω    -64.00  57.00   1.00  100.00    --   20.34 -57.00  60.00  121
  3  ω    -61.00   2.00   1.00  100.00    --  -21.12  84.00 -19.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0097992000
_diffrn_orient_matrix_UB_12      -0.0291315000
_diffrn_orient_matrix_UB_13      -0.0286772000
_diffrn_orient_matrix_UB_21      0.0187136000
_diffrn_orient_matrix_UB_22      -0.1603242000
_diffrn_orient_matrix_UB_23      0.0127033000
_diffrn_orient_matrix_UB_31      -0.0374185000
_diffrn_orient_matrix_UB_32      -0.0878808000
_diffrn_orient_matrix_UB_33      -0.0136564000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1732
_reflns_number_total             2694
_reflns_odcompleteness_completeness 98.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.008
_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)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C13(H13), C7(H7), C11(H11), C9(H9), C21(H21), C14(H14), C8(H8),
 C18(H18), C10(H10), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.86467(9) 0.9149(4) 0.45199(8) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.89427(13) 0.6376(5) 0.55469(11) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.45033(13) 0.3070(5) 0.39046(11) 0.0153(5) Uani 1 1 d . . . . .
C16 C 0.39867(12) 0.3820(5) 0.32721(11) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.53322(13) 0.3985(5) 0.41454(11) 0.0167(5) Uani 1 1 d . . . . .
C15 C 0.31709(13) 0.2476(5) 0.32371(11) 0.0164(6) Uani 1 1 d . . . . .
C3 C 0.68455(14) 0.5718(5) 0.45519(11) 0.0183(6) Uani 1 1 d . . . . .
C17 C 0.42083(13) 0.5479(5) 0.27921(11) 0.0168(5) Uani 1 1 d . . . . .
H17 H 0.475590 0.623382 0.291033 0.020 Uiso 1 1 calc R . . . .
C5 C 0.84018(13) 0.7480(5) 0.49019(12) 0.0180(6) Uani 1 1 d . . . . .
C13 C 0.40391(13) 0.1354(5) 0.42394(12) 0.0185(6) Uani 1 1 d . . . . .
H13 H 0.424197 0.055574 0.467238 0.022 Uiso 1 1 calc R . . . .
C7 C 0.97784(13) 0.6824(5) 0.57003(11) 0.0180(6) Uani 1 1 d . . . . .
H7 H 0.999474 0.784106 0.539434 0.022 Uiso 1 1 calc R . . . .
C11 C 0.86312(13) 0.4933(5) 0.60038(11) 0.0181(6) Uani 1 1 d . . . . .
H11 H 0.806304 0.462178 0.590272 0.022 Uiso 1 1 calc R . . . .
C9 C 0.99759(14) 0.4369(5) 0.67507(12) 0.0204(6) Uani 1 1 d . . . . .
H9 H 1.032883 0.368138 0.716138 0.024 Uiso 1 1 calc R . . . .
C21 C 0.24710(13) 0.2615(5) 0.27091(12) 0.0201(6) Uani 1 1 d . . . . .
H21 H 0.200086 0.165774 0.277608 0.024 Uiso 1 1 calc R . . . .
C2 C 0.60395(13) 0.4793(5) 0.43391(11) 0.0174(5) Uani 1 1 d . . . . .
C14 C 0.32479(13) 0.1010(5) 0.38440(11) 0.0187(6) Uani 1 1 d . . . . .
H14 H 0.282260 -0.004903 0.396237 0.022 Uiso 1 1 calc R . . . .
C8 C 1.02919(13) 0.5795(5) 0.62953(11) 0.0200(6) Uani 1 1 d . . . . .
H8 H 1.086105 0.605986 0.639440 0.024 Uiso 1 1 calc R . . . .
C18 C 0.37392(13) 0.6191(5) 0.21605(11) 0.0198(6) Uani 1 1 d . . . . .
H18 H 0.401428 0.729910 0.190187 0.024 Uiso 1 1 calc R . . . .
C10 C 0.91443(13) 0.3954(5) 0.66028(11) 0.0206(6) Uani 1 1 d . . . . .
H10 H 0.892782 0.299731 0.691361 0.025 Uiso 1 1 calc R . . . .
C20 C 0.23585(13) 0.3957(5) 0.20940(12) 0.0210(6) Uani 1 1 d . . . . .
H20 H 0.182410 0.378674 0.179986 0.025 Uiso 1 1 calc R . . . .
C4 C 0.75502(13) 0.6530(5) 0.47284(11) 0.0195(6) Uani 1 1 d . . . . .
C19 C 0.29236(13) 0.5504(5) 0.18560(11) 0.0205(6) Uani 1 1 d . . . . .
H19 H 0.272219 0.620287 0.141699 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 1.231(3) . ?
C6 C5 1.487(3) . ?
C6 C7 1.396(3) . ?
C6 C11 1.395(3) . ?
C12 C16 1.419(3) . ?
C12 C1 1.414(3) . ?
C12 C13 1.414(3) . ?
C16 C15 1.490(3) . ?
C16 C17 1.384(3) . ?
C1 C2 1.208(3) . ?
C15 C21 1.388(3) . ?
C15 C14 1.408(3) . ?
C3 C2 1.377(3) . ?
C3 C4 1.204(3) . ?
C17 C18 1.390(3) . ?
C5 C4 1.455(3) . ?
C13 C14 1.380(3) . ?
C7 C8 1.381(3) . ?
C11 C10 1.382(3) . ?
C9 C8 1.394(3) . ?
C9 C10 1.389(3) . ?
C21 C20 1.395(3) . ?
C18 C19 1.388(3) . ?
C20 C19 1.385(3) . ?

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
C7 C6 C5 119.3(2) . . ?
C11 C6 C5 121.3(2) . . ?
C11 C6 C7 119.4(2) . . ?
C1 C12 C16 124.6(2) . . ?
C1 C12 C13 127.3(2) . . ?
C13 C12 C16 108.05(19) . . ?
C12 C16 C15 106.1(2) . . ?
C17 C16 C12 126.1(2) . . ?
C17 C16 C15 127.7(2) . . ?
C2 C1 C12 178.7(3) . . ?
C21 C15 C16 126.8(2) . . ?
C21 C15 C14 126.5(2) . . ?
C14 C15 C16 106.67(19) . . ?
C4 C3 C2 179.0(3) . . ?
C16 C17 C18 128.8(2) . . ?
O1 C5 C6 122.7(2) . . ?
O1 C5 C4 119.8(2) . . ?
C4 C5 C6 117.5(2) . . ?
C14 C13 C12 109.9(2) . . ?
C8 C7 C6 120.2(2) . . ?
C10 C11 C6 120.4(2) . . ?
C10 C9 C8 119.9(2) . . ?
C15 C21 C20 129.3(2) . . ?
C1 C2 C3 179.3(3) . . ?
C13 C14 C15 109.2(2) . . ?
C7 C8 C9 120.1(2) . . ?
C19 C18 C17 128.8(2) . . ?
C11 C10 C9 120.1(2) . . ?
C19 C20 C21 128.5(2) . . ?
C3 C4 C5 176.5(3) . . ?
C20 C19 C18 129.9(2) . . ?

_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 1.091
_oxdiff_exptl_absorpt_empirical_full_min 0.917



_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3bh
_database_code_depnum_ccdc_archive 'CCDC 1970437'
loop_
_audit_author_name
_audit_author_address
'Bartlomiej Pigulski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2020-12-20 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.917(2)
_cell_length_b                   10.694(3)
_cell_length_c                   14.206(4)
_cell_angle_alpha                73.17(3)
_cell_angle_beta                 81.00(3)
_cell_angle_gamma                71.94(3)
_cell_volume                     953.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5935
_cell_measurement_theta_min      3.0015
_cell_measurement_theta_max      36.8500

_exptl_crystal_description       plates
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.816
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.165
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'KUMA KM4 CCD'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            18476
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         36.949
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8213
_reflns_number_gt                5839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1029P)²+0.1171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8213
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C5 C -0.16423(17) 1.05212(11) 0.18720(9) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.19826(18) 0.37561(11) 0.07559(9) 0.0176(2) Uani 1 1 d . . . . .
H12 H 0.1839 0.4408 0.0135 0.021 Uiso 1 1 calc R U . . .
C6 C -0.20616(18) 1.07765(12) 0.28124(9) 0.0189(2) Uani 1 1 d . . . . .
H6 H -0.1802 1.0040 0.3386 0.023 Uiso 1 1 calc R U . . .
C15 C 0.19125(16) 0.28356(10) 0.24387(8) 0.01451(19) Uani 1 1 d . . . . .
C1 C 0.08722(18) 0.54384(11) 0.17577(9) 0.0180(2) Uani 1 1 d . . . . .
C14 C 0.26536(16) 0.17356(10) 0.19143(8) 0.01470(19) Uani 1 1 d . . . . .
C11 C 0.15216(17) 0.40792(11) 0.16856(9) 0.0167(2) Uani 1 1 d . . . . .
C8 C -0.32339(17) 1.31516(11) 0.20516(10) 0.0190(2) Uani 1 1 d . . . . .
C19 C 0.33204(17) -0.04688(11) 0.32622(9) 0.0164(2) Uani 1 1 d . . . . .
C20 C 0.32545(16) 0.03297(11) 0.22866(8) 0.01556(19) Uani 1 1 d . . . . .
H20 H 0.3691 -0.0170 0.1800 0.019 Uiso 1 1 calc R U . . .
C10 C -0.20365(18) 1.16075(11) 0.10307(9) 0.0191(2) Uani 1 1 d . . . . .
H10 H -0.1741 1.1436 0.0396 0.023 Uiso 1 1 calc R U . . .
C17 C 0.20602(18) 0.14060(11) 0.41680(9) 0.0188(2) Uani 1 1 d . . . . .
H17 H 0.1800 0.1479 0.4830 0.023 Uiso 1 1 calc R U . . .
C4 C -0.08432(19) 0.91534(11) 0.17907(9) 0.0193(2) Uani 1 1 d . . . . .
C13 C 0.26677(17) 0.23632(11) 0.08825(8) 0.0165(2) Uani 1 1 d . . . . .
C3 C -0.02444(19) 0.79725(11) 0.17590(9) 0.0194(2) Uani 1 1 d . . . . .
N1 N -0.40545(17) 1.45544(11) 0.21522(10) 0.0249(2) Uani 1 1 d . . . . .
C16 C 0.16533(17) 0.26700(11) 0.34614(9) 0.01613(19) Uani 1 1 d . . . . .
C23 C 0.40381(18) -0.20157(11) 0.34346(9) 0.0183(2) Uani 1 1 d . . . . .
H23 H 0.4318 -0.2222 0.2775 0.022 Uiso 1 1 calc R U . . .
C7 C -0.28521(18) 1.20986(12) 0.29026(10) 0.0204(2) Uani 1 1 d . . . . .
H7 H -0.3127 1.2281 0.3534 0.024 Uiso 1 1 calc R U . . .
C18 C 0.27711(19) 0.00669(11) 0.40877(9) 0.0194(2) Uani 1 1 d . . . . .
H18 H 0.2907 -0.0600 0.4702 0.023 Uiso 1 1 calc R U . . .
C9 C -0.28563(18) 1.29344(11) 0.11139(10) 0.0201(2) Uani 1 1 d . . . . .
H9 H -0.3151 1.3674 0.0545 0.024 Uiso 1 1 calc R U . . .
O1 O -0.43551(18) 1.47213(11) 0.29944(9) 0.0353(3) Uani 1 1 d . . . . .
C25 C 0.24131(19) -0.26928(12) 0.40173(10) 0.0214(2) Uani 1 1 d . . . . .
H25A H 0.2137 -0.2528 0.4675 0.032 Uiso 1 1 calc R U . . .
H25B H 0.2904 -0.3675 0.4079 0.032 Uiso 1 1 calc R U . . .
H25C H 0.1158 -0.2310 0.3671 0.032 Uiso 1 1 calc R U . . .
O2 O -0.43936(17) 1.54829(10) 0.13966(9) 0.0349(3) Uani 1 1 d . . . . .
C2 C 0.03723(19) 0.66406(11) 0.17396(9) 0.0204(2) Uani 1 1 d . . . . .
C22 C 0.08671(19) 0.39136(11) 0.38586(9) 0.0198(2) Uani 1 1 d . . . . .
H22A H 0.1817 0.4474 0.3637 0.030 Uiso 1 1 calc R U . . .
H22B H 0.0747 0.3633 0.4581 0.030 Uiso 1 1 calc R U . . .
H22C H -0.0474 0.4443 0.3617 0.030 Uiso 1 1 calc R U . . .
C24 C 0.60198(19) -0.26435(12) 0.39626(11) 0.0239(2) Uani 1 1 d . . . . .
H24A H 0.7063 -0.2212 0.3589 0.036 Uiso 1 1 calc R U . . .
H24B H 0.6492 -0.3622 0.4011 0.036 Uiso 1 1 calc R U . . .
H24C H 0.5771 -0.2497 0.4626 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3339(2) 0.16499(12) 0.00753(9) 0.0212(2) Uani 1 1 d . . . . .
H21A H 0.3197 0.2323 -0.0565 0.032 Uiso 1 1 calc R U . . .
H21B H 0.2492 0.1045 0.0129 0.032 Uiso 1 1 calc R U . . .
H21C H 0.4770 0.1114 0.0132 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C5 C10 1.3978(17) . ?
C5 C6 1.4085(17) . ?
C5 C4 1.4265(16) . ?
C12 C13 1.3819(16) . ?
C12 C11 1.4247(17) . ?
C12 H12 0.9500 . ?
C6 C7 1.3850(17) . ?
C6 H6 0.9500 . ?
C15 C16 1.4012(17) . ?
C15 C11 1.4247(16) . ?
C15 C14 1.4885(16) . ?
C1 C2 1.2170(16) . ?
C1 C11 1.4113(16) . ?
C14 C20 1.3906(16) . ?
C14 C13 1.4243(17) . ?
C8 C7 1.3880(19) . ?
C8 C9 1.3889(18) . ?
C8 N1 1.4711(16) . ?
C19 C20 1.4008(17) . ?
C19 C18 1.4008(17) . ?
C19 C23 1.5288(16) . ?
C20 H20 0.9500 . ?
C10 C9 1.3879(16) . ?
C10 H10 0.9500 . ?
C17 C18 1.3950(16) . ?
C17 C16 1.4074(17) . ?
C17 H17 0.9500 . ?
C4 C3 1.2130(16) . ?
C13 C21 1.4942(17) . ?
C3 C2 1.3616(17) . ?
N1 O2 1.2289(17) . ?
N1 O1 1.2367(17) . ?
C16 C22 1.5076(16) . ?
C23 C25 1.5295(18) . ?
C23 C24 1.5335(18) . ?
C23 H23 1.0000 . ?
C7 H7 0.9500 . ?
C18 H18 0.9500 . ?
C9 H9 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C10 C5 C6 119.71(10) . . ?
C10 C5 C4 120.78(11) . . ?
C6 C5 C4 119.51(11) . . ?
C13 C12 C11 110.61(11) . . ?
C13 C12 H12 124.7 . . ?
C11 C12 H12 124.7 . . ?
C7 C6 C5 120.14(11) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C16 C15 C11 127.57(10) . . ?
C16 C15 C14 126.75(10) . . ?
C11 C15 C14 105.67(10) . . ?
C2 C1 C11 174.64(13) . . ?
C20 C14 C13 122.07(11) . . ?
C20 C14 C15 130.18(11) . . ?
C13 C14 C15 107.75(9) . . ?
C1 C11 C15 130.21(11) . . ?
C1 C11 C12 121.71(11) . . ?
C15 C11 C12 108.04(10) . . ?
C7 C8 C9 122.74(11) . . ?
C7 C8 N1 118.31(11) . . ?
C9 C8 N1 118.95(11) . . ?
C20 C19 C18 123.86(10) . . ?
C20 C19 C23 117.98(10) . . ?
C18 C19 C23 118.16(10) . . ?
C14 C20 C19 130.47(11) . . ?
C14 C20 H20 114.8 . . ?
C19 C20 H20 114.8 . . ?
C9 C10 C5 120.59(11) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C18 C17 C16 132.62(11) . . ?
C18 C17 H17 113.7 . . ?
C16 C17 H17 113.7 . . ?
C3 C4 C5 176.51(13) . . ?
C12 C13 C14 107.92(11) . . ?
C12 C13 C21 125.75(11) . . ?
C14 C13 C21 126.31(10) . . ?
C4 C3 C2 178.19(14) . . ?
O2 N1 O1 124.27(12) . . ?
O2 N1 C8 118.06(12) . . ?
O1 N1 C8 117.67(12) . . ?
C15 C16 C17 124.69(10) . . ?
C15 C16 C22 119.15(10) . . ?
C17 C16 C22 116.16(11) . . ?
C19 C23 C25 112.14(10) . . ?
C19 C23 C24 111.84(10) . . ?
C25 C23 C24 109.43(10) . . ?
C19 C23 H23 107.8 . . ?
C25 C23 H23 107.8 . . ?
C24 C23 H23 107.8 . . ?
C6 C7 C8 118.59(12) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C17 C18 C19 131.44(11) . . ?
C17 C18 H18 114.3 . . ?
C19 C18 H18 114.3 . . ?
C10 C9 C8 118.23(11) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 C2 C3 177.29(14) . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.084

