##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'APEX3 v2016.1-0'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2019-06-04
_journal_date_accepted     2019-11-30
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2020
_journal_volume     76
_journal_issue      1
_journal_page_first     87
_journal_page_last     92
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229619016127
_journal_coeditor_code     QS3087
_publ_contact_author_name
;
Jorge A. Cabezas
;
_publ_contact_author_address
;
Escuela de Quimica
Universidad de Costa Rica
2060 San Jose
Costa Rica
;
_publ_contact_author_email     jorge.cabezas@ucr.ac.cr
_publ_contact_author_fax
;
506 25112446
;
_publ_contact_author_phone
;
506 25114184
;
_publ_section_title
;
Crystal structure and biological activity of 1,1,4-triphenyl-substituted
1,3-enyne compounds
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Pineda, Leslie W.' .
;
Escuela de Química
Universidad de Costa Rica
11501 San José
Costa Rica
Centro de Electroquímica y Energía Química (CELEQ)
Universidad de Costa Rica
11501 San José
Costa Rica
;
    'Arias, María Laura' .
;
Centro de Investigación en Enfermedades Tropicales (CIET)
Facultad de Microbiología
Universidad de Costa Rica
11501 San José
Costa Rica
;
    'Cabezas, Jorge A.' .
;
Escuela de Química
Universidad de Costa Rica
11501 San José
Costa Rica
;
_publ_section_synopsis
;
A series of three 1,1,4-aromatic trisubstituted 1,3-enynes have been
structurally characterized by X-ray diffraction at 100 K. Biological tests for
one enyne reveal it inhibited the growth of Aspergillus niger. Such
1,3-enynes find widespread applications in organic synthesis and biological
tests.
;
data_JCP_07S
_audit_creation_method     'APEX3 v2016.1-0'
_chemical_name_systematic
;
4-(2-Methoxyphenyl)-1,1-diphenylbut-1-en-3-yne
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H18 O'
_chemical_formula_sum     'C23 H18 O'
_chemical_formula_iupac     'C23 H18 O'
_chemical_formula_weight     310.37
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     10.6325(2)
_cell_length_b     14.7734(2)
_cell_length_c     21.7751(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3420.39(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9909
_cell_measurement_theta_min     4.0604
_cell_measurement_theta_max     68.3060
_cell_measurement_temperature     100.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'clear light yellow'
_exptl_crystal_size_max     0.450
_exptl_crystal_size_mid     0.350
_exptl_crystal_size_min     0.250
_exptl_crystal_density_diffrn     1.205
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu     0.557
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_absorpt_correction_T_min     0.6629
_exptl_absorpt_correction_T_max     0.7531
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.(2)
_diffrn_source     'Incoatec Microsource'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     'mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_method     'omega scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     27165
_diffrn_reflns_av_R_equivalents     0.0488
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_theta_min     4.06
_diffrn_reflns_theta_max     68.30
_diffrn_reflns_theta_full     68.30
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_refine_special_details
;
;
_reflns_number_total     3129
_reflns_number_gt     2681
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0520
_refine_ls_R_factor_gt     0.0433
_refine_ls_wR_factor_gt     0.1047
_refine_ls_wR_factor_ref     0.1100
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     3129
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0495P)²+1.7874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.319
_refine_diff_density_min     -0.247
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.00168(17)
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'
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
shelXle (Hübschle et al.,  2011)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and
Mercury (Macrae et al.,  2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.81307(10) 0.58400(7) 0.40917(5) 0.0302(3) Uani d 1 . .
    C C1 0.35943(14) 0.36061(9) 0.40946(6) 0.0204(3) Uani d 1 . .
    C C2 0.32376(13) 0.27620(10) 0.44219(7) 0.0216(3) Uani d 1 . .
    C C3 0.25780(14) 0.20732(10) 0.41220(8) 0.0282(4) Uani d 1 . .
    H H3 0.2311 0.2156 0.3709 0.034 Uiso calc 1 . .
    C C4 0.23109(15) 0.12685(11) 0.44246(9) 0.0369(4) Uani d 1 . .
    H H4 0.1874 0.08 0.4215 0.044 Uiso calc 1 . .
    C C5 0.26775(16) 0.11423(12) 0.50312(9) 0.0397(5) Uani d 1 . .
    H H5 0.2496 0.0589 0.5236 0.048 Uiso calc 1 . .
    C C6 0.33078(16) 0.18274(12) 0.53345(8) 0.0350(4) Uani d 1 . .
    H H6 0.3551 0.1747 0.5751 0.042 Uiso calc 1 . .
    C C7 0.35865(14) 0.26295(11) 0.50356(7) 0.0271(3) Uani d 1 . .
    H H7 0.402 0.3096 0.5249 0.033 Uiso calc 1 . .
    C C8 0.26657(14) 0.40265(9) 0.36748(6) 0.0204(3) Uani d 1 . .
    C C9 0.13830(14) 0.40071(10) 0.38151(7) 0.0250(3) Uani d 1 . .
    H H9 0.1102 0.3683 0.4166 0.03 Uiso calc 1 . .
    C C10 0.05153(16) 0.44541(11) 0.34487(8) 0.0317(4) Uani d 1 . .
    H H10 -0.0353 0.4436 0.3551 0.038 Uiso calc 1 . .
    C C11 0.09088(17) 0.49242(11) 0.29361(8) 0.0358(4) Uani d 1 . .
    H H11 0.0317 0.5243 0.2691 0.043 Uiso calc 1 . .
    C C12 0.21694(17) 0.49281(12) 0.27806(7) 0.0360(4) Uani d 1 . .
    H H12 0.2441 0.524 0.2423 0.043 Uiso calc 1 . .
    C C13 0.30365(16) 0.44802(11) 0.31427(7) 0.0281(4) Uani d 1 . .
    H H13 0.3898 0.4481 0.3028 0.034 Uiso calc 1 . .
    C C14 0.47479(14) 0.39614(10) 0.42026(7) 0.0237(3) Uani d 1 . .
    H H14 0.5276 0.3628 0.4472 0.028 Uiso calc 1 . .
    C C15 0.52618(14) 0.47750(10) 0.39594(7) 0.0243(3) Uani d 1 . .
    C C16 0.57677(14) 0.54474(10) 0.37683(7) 0.0244(3) Uani d 1 . .
    C C17 0.63718(15) 0.62237(10) 0.35096(7) 0.0252(3) Uani d 1 . .
    C C18 0.76265(16) 0.64074(10) 0.36693(7) 0.0272(4) Uani d 1 . .
    C C19 0.82665(17) 0.71257(12) 0.33937(8) 0.0360(4) Uani d 1 . .
    H H19 0.9119 0.7245 0.3496 0.043 Uiso calc 1 . .
    C C20 0.7645(2) 0.76611(12) 0.29700(9) 0.0429(5) Uani d 1 . .
    H H20 0.8083 0.8145 0.2778 0.051 Uiso calc 1 . .
    C C21 0.64020(18) 0.75079(12) 0.28198(8) 0.0398(4) Uani d 1 . .
    H H21 0.5987 0.789 0.2533 0.048 Uiso calc 1 . .
    C C22 0.57572(17) 0.67880(11) 0.30908(7) 0.0319(4) Uani d 1 . .
    H H22 0.49 0.6682 0.299 0.038 Uiso calc 1 . .
    C C23 0.92553(16) 0.61278(13) 0.43930(9) 0.0396(4) Uani d 1 . .
    H H23A 0.9948 0.6143 0.4096 0.059 Uiso calc 1 . .
    H H23B 0.946 0.5704 0.4724 0.059 Uiso calc 1 . .
    H H23C 0.913 0.6734 0.4565 0.059 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C18 . 1.3550(19) ?
    O1 C23 . 1.4287(19) ?
    C1 C14 . 1.355(2) yes
    C1 C8 . 1.482(2) yes
    C1 C2 . 1.485(2) yes
    C2 C3 . 1.398(2) ?
    C2 C7 . 1.401(2) ?
    C3 C4 . 1.388(2) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.390(3) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.384(2) ?
    C6 H6 . 0.95 ?
    C7 H7 . 0.95 ?
    C8 C13 . 1.395(2) ?
    C8 C9 . 1.398(2) ?
    C9 C10 . 1.387(2) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.380(2) ?
    C10 H10 . 0.95 ?
    C11 C12 . 1.383(3) ?
    C11 H11 . 0.95 ?
    C12 C13 . 1.382(2) ?
    C12 H12 . 0.95 ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.423(2) yes
    C14 H14 . 0.95 ?
    C15 C16 . 1.204(2) yes
    C16 C17 . 1.430(2) yes
    C17 C22 . 1.398(2) ?
    C17 C18 . 1.405(2) ?
    C18 C19 . 1.396(2) ?
    C19 C20 . 1.383(3) ?
    C19 H19 . 0.95 ?
    C20 C21 . 1.380(3) ?
    C20 H20 . 0.95 ?
    C21 C22 . 1.396(2) ?
    C21 H21 . 0.95 ?
    C22 H22 . 0.95 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C18 O1 C23 . . 117.30(13) ?
    C14 C1 C8 . . 123.22(13) yes
    C14 C1 C2 . . 118.24(13) yes
    C8 C1 C2 . . 118.53(12) yes
    C3 C2 C7 . . 118.48(14) ?
    C3 C2 C1 . . 121.01(13) ?
    C7 C2 C1 . . 120.49(13) ?
    C4 C3 C2 . . 120.28(15) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 120.57(16) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C6 C5 C4 . . 119.47(15) ?
    C6 C5 H5 . . 120.3 ?
    C4 C5 H5 . . 120.3 ?
    C5 C6 C7 . . 120.42(16) ?
    C5 C6 H6 . . 119.8 ?
    C7 C6 H6 . . 119.8 ?
    C6 C7 C2 . . 120.76(16) ?
    C6 C7 H7 . . 119.6 ?
    C2 C7 H7 . . 119.6 ?
    C13 C8 C9 . . 117.84(14) ?
    C13 C8 C1 . . 121.68(14) ?
    C9 C8 C1 . . 120.43(13) ?
    C10 C9 C8 . . 120.89(14) ?
    C10 C9 H9 . . 119.6 ?
    C8 C9 H9 . . 119.6 ?
    C11 C10 C9 . . 120.22(16) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C10 C11 C12 . . 119.62(15) ?
    C10 C11 H11 . . 120.2 ?
    C12 C11 H11 . . 120.2 ?
    C13 C12 C11 . . 120.34(15) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C8 . . 121.01(15) ?
    C12 C13 H13 . . 119.5 ?
    C8 C13 H13 . . 119.5 ?
    C1 C14 C15 . . 127.63(14) yes
    C1 C14 H14 . . 116.2 ?
    C15 C14 H14 . . 116.2 ?
    C16 C15 C14 . . 175.94(16) yes
    C15 C16 C17 . . 176.93(16) yes
    C22 C17 C18 . . 119.35(15) ?
    C22 C17 C16 . . 121.69(15) ?
    C18 C17 C16 . . 118.94(14) ?
    O1 C18 C19 . . 124.69(15) ?
    O1 C18 C17 . . 115.10(13) ?
    C19 C18 C17 . . 120.21(15) ?
    C20 C19 C18 . . 119.24(17) ?
    C20 C19 H19 . . 120.4 ?
    C18 C19 H19 . . 120.4 ?
    C21 C20 C19 . . 121.44(17) ?
    C21 C20 H20 . . 119.3 ?
    C19 C20 H20 . . 119.3 ?
    C20 C21 C22 . . 119.67(17) ?
    C20 C21 H21 . . 120.2 ?
    C22 C21 H21 . . 120.2 ?
    C21 C22 C17 . . 120.03(17) ?
    C21 C22 H22 . . 120.0 ?
    C17 C22 H22 . . 120.0 ?
    O1 C23 H23A . . 109.5 ?
    O1 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    O1 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C14 C1 C2 C3 . . . . -139.45(15) ?
    C8 C1 C2 C3 . . . . 41.58(19) ?
    C14 C1 C2 C7 . . . . 38.8(2) ?
    C8 C1 C2 C7 . . . . -140.15(14) ?
    C7 C2 C3 C4 . . . . -1.8(2) ?
    C1 C2 C3 C4 . . . . 176.53(14) ?
    C2 C3 C4 C5 . . . . 1.0(2) ?
    C3 C4 C5 C6 . . . . 0.3(2) ?
    C4 C5 C6 C7 . . . . -0.8(2) ?
    C5 C6 C7 C2 . . . . -0.1(2) ?
    C3 C2 C7 C6 . . . . 1.3(2) ?
    C1 C2 C7 C6 . . . . -176.99(13) ?
    C14 C1 C8 C13 . . . . 34.7(2) ?
    C2 C1 C8 C13 . . . . -146.42(14) ?
    C14 C1 C8 C9 . . . . -142.96(15) ?
    C2 C1 C8 C9 . . . . 35.97(19) ?
    C13 C8 C9 C10 . . . . -2.4(2) ?
    C1 C8 C9 C10 . . . . 175.33(14) ?
    C8 C9 C10 C11 . . . . 0.2(2) ?
    C9 C10 C11 C12 . . . . 1.7(3) ?
    C10 C11 C12 C13 . . . . -1.4(3) ?
    C11 C12 C13 C8 . . . . -0.9(3) ?
    C9 C8 C13 C12 . . . . 2.7(2) ?
    C1 C8 C13 C12 . . . . -174.99(14) ?
    C8 C1 C14 C15 . . . . 1.5(2) ?
    C2 C1 C14 C15 . . . . -177.46(14) ?
    C23 O1 C18 C19 . . . . 17.2(2) ?
    C23 O1 C18 C17 . . . . -163.43(14) ?
    C22 C17 C18 O1 . . . . 178.13(13) ?
    C16 C17 C18 O1 . . . . -3.5(2) ?
    C22 C17 C18 C19 . . . . -2.5(2) ?
    C16 C17 C18 C19 . . . . 175.83(15) ?
    O1 C18 C19 C20 . . . . -179.67(15) ?
    C17 C18 C19 C20 . . . . 1.0(2) ?
    C18 C19 C20 C21 . . . . 0.8(3) ?
    C19 C20 C21 C22 . . . . -1.2(3) ?
    C20 C21 C22 C17 . . . . -0.3(3) ?
    C18 C17 C22 C21 . . . . 2.1(2) ?
    C16 C17 C22 C21 . . . . -176.13(15) ?
data_JCP_10S
_audit_creation_method     'APEX3 v2016.1-0'
_chemical_name_systematic
;
4-(4-Nitrophenyl)-1,1-diphenylbut-1-en-3-yne
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H15 N O2'
_chemical_formula_sum     'C22 H15 N O2'
_chemical_formula_iupac     'C22 H15 N O2'
_chemical_formula_weight     325.36
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_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     9.6548(5)
_cell_length_b     22.2107(10)
_cell_length_c     7.9248(4)
_cell_angle_alpha     90
_cell_angle_beta     105.7490(10)
_cell_angle_gamma     90
_cell_volume     1635.60(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9866
_cell_measurement_theta_min     2.8238
_cell_measurement_theta_max     27.5029
_cell_measurement_temperature     100.(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     'clear pale yellow'
_exptl_crystal_size_max     0.350
_exptl_crystal_size_mid     0.250
_exptl_crystal_size_min     0.150
_exptl_crystal_density_diffrn     1.321
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_absorpt_correction_T_min     0.7170
_exptl_absorpt_correction_T_max     0.7456
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.(2)
_diffrn_source     'Incoatec Microsource'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_method     'omega scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     40247
_diffrn_reflns_av_R_equivalents     0.0455
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_theta_min     2.82
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
;
_reflns_number_total     3763
_reflns_number_gt     2822
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_gt     0.0898
_refine_ls_wR_factor_ref     0.0995
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     3763
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0437P)²+0.5574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.260
_refine_diff_density_min     -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
shelXle (Hübschle et al.,  2011)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and
Mercury (Macrae et al.,  2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.06547(11) 0.57359(5) 1.24915(14) 0.0290(3) Uani d 1 . .
    O O2 0.96091(10) 0.66032(4) 1.23968(13) 0.0261(2) Uani d 1 . .
    N N1 0.96049(12) 0.60708(5) 1.19807(15) 0.0205(3) Uani d 1 . .
    C C1 0.23501(14) 0.39605(6) 0.47305(16) 0.0155(3) Uani d 1 . .
    C C2 0.35549(14) 0.35375(6) 0.54916(16) 0.0157(3) Uani d 1 . .
    C C3 0.32967(14) 0.29915(6) 0.62236(17) 0.0181(3) Uani d 1 . .
    H H3 0.2337 0.2878 0.6172 0.022 Uiso calc 1 . .
    C C4 0.44266(15) 0.26120(6) 0.70263(18) 0.0209(3) Uani d 1 . .
    H H4 0.4238 0.2247 0.7548 0.025 Uiso calc 1 . .
    C C5 0.58279(15) 0.27639(6) 0.70686(18) 0.0215(3) Uani d 1 . .
    H H5 0.66 0.2504 0.7617 0.026 Uiso calc 1 . .
    C C6 0.60984(15) 0.32977(6) 0.63058(18) 0.0214(3) Uani d 1 . .
    H H6 0.7055 0.3399 0.6311 0.026 Uiso calc 1 . .
    C C7 0.49756(14) 0.36836(6) 0.55356(17) 0.0181(3) Uani d 1 . .
    H H7 0.5172 0.4051 0.5032 0.022 Uiso calc 1 . .
    C C8 0.09902(14) 0.37215(6) 0.35605(16) 0.0161(3) Uani d 1 . .
    C C9 0.09857(15) 0.32199(6) 0.24950(17) 0.0197(3) Uani d 1 . .
    H H9 0.1862 0.3014 0.2566 0.024 Uiso calc 1 . .
    C C10 -0.02771(16) 0.30173(6) 0.13340(18) 0.0244(3) Uani d 1 . .
    H H10 -0.0259 0.2678 0.0612 0.029 Uiso calc 1 . .
    C C11 -0.15640(15) 0.33103(7) 0.12283(18) 0.0248(3) Uani d 1 . .
    H H11 -0.2427 0.3178 0.0417 0.03 Uiso calc 1 . .
    C C12 -0.15856(15) 0.37963(7) 0.23106(19) 0.0257(3) Uani d 1 . .
    H H12 -0.2471 0.3992 0.2262 0.031 Uiso calc 1 . .
    C C13 -0.03271(14) 0.40003(6) 0.34644(18) 0.0212(3) Uani d 1 . .
    H H13 -0.0359 0.4335 0.4201 0.025 Uiso calc 1 . .
    C C14 0.24632(14) 0.45581(6) 0.50884(17) 0.0181(3) Uani d 1 . .
    H H14 0.1693 0.4809 0.4476 0.022 Uiso calc 1 . .
    C C15 0.36393(15) 0.48402(6) 0.63032(17) 0.0179(3) Uani d 1 . .
    C C16 0.46033(14) 0.50917(6) 0.73385(17) 0.0188(3) Uani d 1 . .
    C C17 0.58479(14) 0.53456(6) 0.85444(17) 0.0177(3) Uani d 1 . .
    C C18 0.70564(15) 0.49816(6) 0.92069(17) 0.0203(3) Uani d 1 . .
    H H18 0.7034 0.457 0.8873 0.024 Uiso calc 1 . .
    C C19 0.82814(15) 0.52171(6) 1.03438(18) 0.0200(3) Uani d 1 . .
    H H19 0.9103 0.4971 1.0798 0.024 Uiso calc 1 . .
    C C20 0.82900(14) 0.58180(6) 1.08093(16) 0.0177(3) Uani d 1 . .
    C C21 0.71092(14) 0.61893(6) 1.01923(17) 0.0183(3) Uani d 1 . .
    H H21 0.714 0.66 1.0539 0.022 Uiso calc 1 . .
    C C22 0.58867(14) 0.59503(6) 0.90637(17) 0.0189(3) Uani d 1 . .
    H H22 0.5063 0.6198 0.8634 0.023 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N1 . 1.2336(14) ?
    O2 N1 . 1.2273(15) ?
    N1 C20 . 1.4659(17) ?
    C1 C14 . 1.3554(18) yes
    C1 C8 . 1.4848(17) yes
    C1 C2 . 1.4895(18) yes
    C2 C3 . 1.3957(18) ?
    C2 C7 . 1.4007(18) ?
    C3 C4 . 1.3886(18) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.386(2) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.387(2) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.3868(19) ?
    C6 H6 . 0.95 ?
    C7 H7 . 0.95 ?
    C8 C9 . 1.3971(18) ?
    C8 C13 . 1.3981(18) ?
    C9 C10 . 1.3881(19) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.385(2) ?
    C10 H10 . 0.95 ?
    C11 C12 . 1.382(2) ?
    C11 H11 . 0.95 ?
    C12 C13 . 1.3837(19) ?
    C12 H12 . 0.95 ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.4196(19) yes
    C14 H14 . 0.95 no
    C15 C16 . 1.1987(18) yes
    C16 C17 . 1.4324(19) yes
    C17 C18 . 1.3994(19) ?
    C17 C22 . 1.4023(19) ?
    C18 C19 . 1.3805(19) ?
    C18 H18 . 0.95 ?
    C19 C20 . 1.3841(19) ?
    C19 H19 . 0.95 ?
    C20 C21 . 1.3843(18) ?
    C21 C22 . 1.3790(18) ?
    C21 H21 . 0.95 ?
    C22 H22 . 0.95 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 N1 O1 . . 123.39(12) ?
    O2 N1 C20 . . 118.58(11) ?
    O1 N1 C20 . . 118.03(11) ?
    C14 C1 C8 . . 119.22(12) yes
    C14 C1 C2 . . 121.54(12) yes
    C8 C1 C2 . . 119.23(11) yes
    C3 C2 C7 . . 118.37(12) ?
    C3 C2 C1 . . 120.56(11) ?
    C7 C2 C1 . . 121.05(11) ?
    C4 C3 C2 . . 120.74(12) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C5 C4 C3 . . 120.25(13) ?
    C5 C4 H4 . . 119.9 ?
    C3 C4 H4 . . 119.9 ?
    C4 C5 C6 . . 119.70(12) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C7 C6 C5 . . 120.19(13) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C6 C7 C2 . . 120.72(12) ?
    C6 C7 H7 . . 119.6 ?
    C2 C7 H7 . . 119.6 ?
    C9 C8 C13 . . 117.83(12) ?
    C9 C8 C1 . . 121.31(12) ?
    C13 C8 C1 . . 120.85(12) ?
    C10 C9 C8 . . 121.15(13) ?
    C10 C9 H9 . . 119.4 ?
    C8 C9 H9 . . 119.4 ?
    C11 C10 C9 . . 119.99(13) ?
    C11 C10 H10 . . 120.0 ?
    C9 C10 H10 . . 120.0 ?
    C12 C11 C10 . . 119.59(13) ?
    C12 C11 H11 . . 120.2 ?
    C10 C11 H11 . . 120.2 ?
    C11 C12 C13 . . 120.49(14) ?
    C11 C12 H12 . . 119.8 ?
    C13 C12 H12 . . 119.8 ?
    C12 C13 C8 . . 120.90(13) ?
    C12 C13 H13 . . 119.5 ?
    C8 C13 H13 . . 119.5 ?
    C1 C14 C15 . . 125.33(12) yes
    C1 C14 H14 . . 117.3 ?
    C15 C14 H14 . . 117.3 no
    C16 C15 C14 . . 177.95(15) yes
    C15 C16 C17 . . 174.26(14) yes
    C18 C17 C22 . . 119.35(12) ?
    C18 C17 C16 . . 119.07(12) ?
    C22 C17 C16 . . 121.57(12) ?
    C19 C18 C17 . . 120.36(12) ?
    C19 C18 H18 . . 119.8 ?
    C17 C18 H18 . . 119.8 ?
    C18 C19 C20 . . 118.78(13) ?
    C18 C19 H19 . . 120.6 ?
    C20 C19 H19 . . 120.6 ?
    C19 C20 C21 . . 122.38(12) ?
    C19 C20 N1 . . 118.66(12) ?
    C21 C20 N1 . . 118.95(12) ?
    C22 C21 C20 . . 118.53(12) ?
    C22 C21 H21 . . 120.7 ?
    C20 C21 H21 . . 120.7 ?
    C21 C22 C17 . . 120.59(12) ?
    C21 C22 H22 . . 119.7 ?
    C17 C22 H22 . . 119.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C14 C1 C2 C3 . . . . 134.16(14) ?
    C8 C1 C2 C3 . . . . -45.48(17) ?
    C14 C1 C2 C7 . . . . -44.07(18) ?
    C8 C1 C2 C7 . . . . 136.29(13) ?
    C7 C2 C3 C4 . . . . 2.08(19) ?
    C1 C2 C3 C4 . . . . -176.19(12) ?
    C2 C3 C4 C5 . . . . -1.8(2) ?
    C3 C4 C5 C6 . . . . 0.1(2) ?
    C4 C5 C6 C7 . . . . 1.3(2) ?
    C5 C6 C7 C2 . . . . -1.0(2) ?
    C3 C2 C7 C6 . . . . -0.72(19) ?
    C1 C2 C7 C6 . . . . 177.55(12) ?
    C14 C1 C8 C9 . . . . 149.19(13) ?
    C2 C1 C8 C9 . . . . -31.16(18) ?
    C14 C1 C8 C13 . . . . -29.47(18) ?
    C2 C1 C8 C13 . . . . 150.18(12) ?
    C13 C8 C9 C10 . . . . 2.20(19) ?
    C1 C8 C9 C10 . . . . -176.50(12) ?
    C8 C9 C10 C11 . . . . -0.6(2) ?
    C9 C10 C11 C12 . . . . -1.4(2) ?
    C10 C11 C12 C13 . . . . 1.6(2) ?
    C11 C12 C13 C8 . . . . 0.1(2) ?
    C9 C8 C13 C12 . . . . -2.0(2) ?
    C1 C8 C13 C12 . . . . 176.74(13) ?
    C8 C1 C14 C15 . . . . 173.87(12) ?
    C2 C1 C14 C15 . . . . -5.8(2) ?
    C22 C17 C18 C19 . . . . -0.79(19) ?
    C16 C17 C18 C19 . . . . 178.70(12) ?
    C17 C18 C19 C20 . . . . -0.13(19) ?
    C18 C19 C20 C21 . . . . 0.8(2) ?
    C18 C19 C20 N1 . . . . -178.43(12) ?
    O2 N1 C20 C19 . . . . -179.76(12) ?
    O1 N1 C20 C19 . . . . 0.54(18) ?
    O2 N1 C20 C21 . . . . 1.00(18) ?
    O1 N1 C20 C21 . . . . -178.69(12) ?
    C19 C20 C21 C22 . . . . -0.5(2) ?
    N1 C20 C21 C22 . . . . 178.74(12) ?
    C20 C21 C22 C17 . . . . -0.48(19) ?
    C18 C17 C22 C21 . . . . 1.10(19) ?
    C16 C17 C22 C21 . . . . -178.38(12) ?
data_JCP_06S
_chemical_name_systematic
;
4-(2-Methylphenyl)-1,1-diphenylbut-1-en-3-yne
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H18'
_chemical_formula_sum     'C23 H18'
_chemical_formula_iupac     'C23 H18'
_chemical_formula_weight     294.37
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_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     14.3054(3)
_cell_length_b     5.83540(10)
_cell_length_c     19.0365(4)
_cell_angle_alpha     90
_cell_angle_beta     90.9350(10)
_cell_angle_gamma     90
_cell_volume     1588.91(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5897
_cell_measurement_theta_min     3.8353
_cell_measurement_theta_max     68.1862
_cell_measurement_temperature     100.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'clear light yellow'
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.150
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.231
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.524
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_absorpt_correction_T_min     0.6721
_exptl_absorpt_correction_T_max     0.7531
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.(2)
_diffrn_source     'Incoatec Microsource'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     'mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_method     'omega scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     21068
_diffrn_reflns_av_R_equivalents     0.0701
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_theta_min     3.83
_diffrn_reflns_theta_max     68.31
_diffrn_reflns_theta_full     68.31
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_refine_special_details
;
;
_reflns_number_total     2897
_reflns_number_gt     2201
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0715
_refine_ls_R_factor_gt     0.0497
_refine_ls_wR_factor_gt     0.1072
_refine_ls_wR_factor_ref     0.1163
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     2897
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0568P)²+0.3848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.150
_refine_diff_density_min     -0.267
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
shelXle (Hübschle et al.,  2011)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and
Mercury (Macrae et al.,  2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.62818(12) 0.4676(3) 0.34132(9) 0.0187(4) Uani d 1 . .
    C C2 0.52879(12) 0.5072(3) 0.32097(9) 0.0189(4) Uani d 1 . .
    C C3 0.50023(12) 0.7070(3) 0.28601(10) 0.0219(4) Uani d 1 . .
    H H3 0.5449 0.8224 0.2759 0.026 Uiso calc 1 . .
    C C4 0.40756(12) 0.7384(3) 0.26599(10) 0.0237(4) Uani d 1 . .
    H H4 0.3894 0.8738 0.2416 0.028 Uiso calc 1 . .
    C C5 0.34105(12) 0.5730(3) 0.28136(9) 0.0244(4) Uani d 1 . .
    H H5 0.2775 0.5948 0.2677 0.029 Uiso calc 1 . .
    C C6 0.36825(12) 0.3761(3) 0.31683(9) 0.0228(4) Uani d 1 . .
    H H6 0.3229 0.2633 0.3279 0.027 Uiso calc 1 . .
    C C7 0.46079(12) 0.3424(3) 0.33628(9) 0.0208(4) Uani d 1 . .
    H H7 0.4785 0.206 0.3603 0.025 Uiso calc 1 . .
    C C8 0.64544(11) 0.3118(3) 0.40258(9) 0.0185(4) Uani d 1 . .
    C C9 0.60968(12) 0.3669(3) 0.46846(9) 0.0213(4) Uani d 1 . .
    H H9 0.5777 0.5079 0.4748 0.026 Uiso calc 1 . .
    C C10 0.62064(13) 0.2171(3) 0.52448(10) 0.0243(4) Uani d 1 . .
    H H10 0.5964 0.2558 0.5691 0.029 Uiso calc 1 . .
    C C11 0.66701(13) 0.0108(3) 0.51541(10) 0.0249(4) Uani d 1 . .
    H H11 0.6744 -0.0921 0.5538 0.03 Uiso calc 1 . .
    C C12 0.70260(12) -0.0454(3) 0.45040(10) 0.0236(4) Uani d 1 . .
    H H12 0.7343 -0.1869 0.4442 0.028 Uiso calc 1 . .
    C C13 0.69196(12) 0.1047(3) 0.39437(10) 0.0216(4) Uani d 1 . .
    H H13 0.7167 0.0656 0.3499 0.026 Uiso calc 1 . .
    C C14 0.69851(12) 0.5676(3) 0.30626(9) 0.0196(4) Uani d 1 . .
    H H14 0.6826 0.6528 0.2653 0.024 Uiso calc 1 . .
    C C15 0.79494(12) 0.5547(3) 0.32617(9) 0.0200(4) Uani d 1 . .
    C C16 0.87627(12) 0.5582(3) 0.34320(9) 0.0215(4) Uani d 1 . .
    C C17 0.97189(12) 0.5445(3) 0.36746(9) 0.0206(4) Uani d 1 . .
    C C18 0.99968(12) 0.3543(3) 0.40849(9) 0.0225(4) Uani d 1 . .
    C C19 1.09221(13) 0.3434(3) 0.43234(10) 0.0268(4) Uani d 1 . .
    H H19 1.1123 0.2158 0.4597 0.032 Uiso calc 1 . .
    C C20 1.15554(13) 0.5157(3) 0.41682(10) 0.0270(4) Uani d 1 . .
    H H20 1.2181 0.5064 0.4341 0.032 Uiso calc 1 . .
    C C21 1.12775(13) 0.7009(3) 0.37624(10) 0.0261(4) Uani d 1 . .
    H H21 1.1712 0.8184 0.3656 0.031 Uiso calc 1 . .
    C C22 1.03653(12) 0.7149(3) 0.35113(10) 0.0230(4) Uani d 1 . .
    H H22 1.0179 0.841 0.3226 0.028 Uiso calc 1 . .
    C C23 0.93035(13) 0.1711(3) 0.42587(11) 0.0276(4) Uani d 1 . .
    H H23A 0.8993 0.1178 0.3826 0.041 Uiso calc 1 . .
    H H23B 0.8836 0.2333 0.4577 0.041 Uiso calc 1 . .
    H H23C 0.9628 0.0425 0.4486 0.041 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C14 . 1.349(2) yes
    C1 C2 . 1.486(2) yes
    C1 C8 . 1.496(2) yes
    C2 C3 . 1.400(2) ?
    C2 C7 . 1.402(2) ?
    C3 C4 . 1.385(2) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.390(3) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.383(2) ?
    C6 H6 . 0.95 ?
    C7 H7 . 0.95 ?
    C8 C13 . 1.390(2) ?
    C8 C9 . 1.400(2) ?
    C9 C10 . 1.386(3) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.387(3) ?
    C10 H10 . 0.95 ?
    C11 C12 . 1.385(3) ?
    C11 H11 . 0.95 ?
    C12 C13 . 1.387(2) ?
    C12 H12 . 0.95 ?
    C13 H13 . 0.95 ?
    C14 C15 . 1.427(2) yes
    C14 H14 . 0.95 ?
    C15 C16 . 1.203(3) yes
    C16 C17 . 1.439(2) yes
    C17 C22 . 1.396(2) ?
    C17 C18 . 1.411(3) ?
    C18 C19 . 1.394(3) ?
    C18 C23 . 1.499(2) ?
    C19 C20 . 1.389(3) ?
    C19 H19 . 0.95 ?
    C20 C21 . 1.383(3) ?
    C20 H20 . 0.95 ?
    C21 C22 . 1.385(2) ?
    C21 H21 . 0.95 ?
    C22 H22 . 0.95 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C14 C1 C2 . . 121.47(16) yes
    C14 C1 C8 . . 122.24(16) yes
    C2 C1 C8 . . 116.29(14) yes
    C3 C2 C7 . . 118.17(16) ?
    C3 C2 C1 . . 121.62(16) ?
    C7 C2 C1 . . 120.21(16) ?
    C4 C3 C2 . . 120.76(17) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 120.36(17) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C6 C5 C4 . . 119.40(17) ?
    C6 C5 H5 . . 120.3 ?
    C4 C5 H5 . . 120.3 ?
    C7 C6 C5 . . 120.57(17) ?
    C7 C6 H6 . . 119.7 ?
    C5 C6 H6 . . 119.7 ?
    C6 C7 C2 . . 120.73(17) ?
    C6 C7 H7 . . 119.6 ?
    C2 C7 H7 . . 119.6 ?
    C13 C8 C9 . . 118.90(17) ?
    C13 C8 C1 . . 120.94(16) ?
    C9 C8 C1 . . 120.05(15) ?
    C10 C9 C8 . . 120.41(17) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 120.01(18) ?
    C9 C10 H10 . . 120.0 ?
    C11 C10 H10 . . 120.0 ?
    C12 C11 C10 . . 120.02(18) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 120.01(17) ?
    C11 C12 H12 . . 120.0 ?
    C13 C12 H12 . . 120.0 ?
    C12 C13 C8 . . 120.65(17) ?
    C12 C13 H13 . . 119.7 ?
    C8 C13 H13 . . 119.7 ?
    C1 C14 C15 . . 124.86(17) yes
    C1 C14 H14 . . 117.6 ?
    C15 C14 H14 . . 117.6 ?
    C16 C15 C14 . . 176.04(19) yes
    C15 C16 C17 . . 174.8(2) yes
    C22 C17 C18 . . 120.12(16) ?
    C22 C17 C16 . . 121.25(17) ?
    C18 C17 C16 . . 118.63(16) ?
    C19 C18 C17 . . 118.30(17) ?
    C19 C18 C23 . . 121.58(17) ?
    C17 C18 C23 . . 120.12(16) ?
    C20 C19 C18 . . 121.12(18) ?
    C20 C19 H19 . . 119.4 ?
    C18 C19 H19 . . 119.4 ?
    C21 C20 C19 . . 120.15(17) ?
    C21 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
    C20 C21 C22 . . 119.99(18) ?
    C20 C21 H21 . . 120.0 ?
    C22 C21 H21 . . 120.0 ?
    C21 C22 C17 . . 120.32(18) ?
    C21 C22 H22 . . 119.8 ?
    C17 C22 H22 . . 119.8 ?
    C18 C23 H23A . . 109.5 ?
    C18 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C18 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C14 C1 C2 C3 . . . . -25.7(3) ?
    C8 C1 C2 C3 . . . . 154.24(16) ?
    C14 C1 C2 C7 . . . . 153.97(17) ?
    C8 C1 C2 C7 . . . . -26.1(2) ?
    C7 C2 C3 C4 . . . . -1.2(3) ?
    C1 C2 C3 C4 . . . . 178.46(17) ?
    C2 C3 C4 C5 . . . . 1.0(3) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . -0.7(3) ?
    C5 C6 C7 C2 . . . . 0.5(3) ?
    C3 C2 C7 C6 . . . . 0.5(3) ?
    C1 C2 C7 C6 . . . . -179.20(16) ?
    C14 C1 C8 C13 . . . . -64.2(2) ?
    C2 C1 C8 C13 . . . . 115.94(18) ?
    C14 C1 C8 C9 . . . . 119.75(19) ?
    C2 C1 C8 C9 . . . . -60.2(2) ?
    C13 C8 C9 C10 . . . . 0.0(3) ?
    C1 C8 C9 C10 . . . . 176.20(16) ?
    C8 C9 C10 C11 . . . . -0.2(3) ?
    C9 C10 C11 C12 . . . . 0.2(3) ?
    C10 C11 C12 C13 . . . . 0.1(3) ?
    C11 C12 C13 C8 . . . . -0.2(3) ?
    C9 C8 C13 C12 . . . . 0.2(3) ?
    C1 C8 C13 C12 . . . . -175.94(16) ?
    C2 C1 C14 C15 . . . . 174.16(16) ?
    C8 C1 C14 C15 . . . . -5.7(3) ?
    C22 C17 C18 C19 . . . . 0.6(3) ?
    C16 C17 C18 C19 . . . . -179.42(17) ?
    C22 C17 C18 C23 . . . . -179.84(17) ?
    C16 C17 C18 C23 . . . . 0.2(3) ?
    C17 C18 C19 C20 . . . . 0.6(3) ?
    C23 C18 C19 C20 . . . . -179.02(18) ?
    C18 C19 C20 C21 . . . . -0.9(3) ?
    C19 C20 C21 C22 . . . . 0.2(3) ?
    C20 C21 C22 C17 . . . . 1.0(3) ?
    C18 C17 C22 C21 . . . . -1.3(3) ?
    C16 C17 C22 C21 . . . . 178.64(17) ?
