#------------------------------------------------------------------------------
#$Date: 2020-02-05 07:54:34 +0200 (Wed, 05 Feb 2020) $
#$Revision: 247890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/18/2021850.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021850
loop_
_publ_author_name
'Pineda, Leslie W.'
'Arias, María Laura'
'Cabezas, Jorge A.'
_publ_section_title
;
 Crystal structures and biological activity of 1,1,4-triphenyl-substituted
 1,3-enyne compounds
;
_journal_coeditor_code           QS3087
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              87
_journal_page_last               92
_journal_paper_doi               10.1107/S2053229619016127
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C23 H18'
_chemical_formula_moiety         'C23 H18'
_chemical_formula_sum            'C23 H18'
_chemical_formula_weight         294.37
_chemical_name_systematic
;
4-(2-Methylphenyl)-1,1-diphenylbut-1-en-3-yne
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.9350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3054(3)
_cell_length_b                   5.83540(10)
_cell_length_c                   19.0365(4)
_cell_measurement_reflns_used    5897
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.1862
_cell_measurement_theta_min      3.8353
_cell_volume                     1588.91(5)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
shelXle (Hübschle et al.,  2011)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and
Mercury (Macrae et al.,  2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21068
_diffrn_reflns_theta_full        68.31
_diffrn_reflns_theta_max         68.31
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'Incoatec Microsource'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0497
_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)+(0.0568P)²+0.3848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                2201
_reflns_number_total             2897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qs3087sup1.cif
_cod_data_source_block           JCP_06S
_cod_depositor_comments
'Adding full bibliography for 2021848--2021850.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2021850
_cod_database_fobs_code          2021850
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_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
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
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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
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)
