#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240373.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_2240373
loop_
_publ_author_name
'Caracelli, Ignez'
'Maganhi, Stella H.'
'Stefani, Hélio A.'
'Gueogjian, Karina'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure of
 3-[2-(4-methylphenyl)ethynyl]-2H-chromen-2-one
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o90
_journal_page_last               o91
_journal_paper_doi               10.1107/S2056989014027790
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C18 H12 O2'
_chemical_formula_moiety         'C18 H12 O2'
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28
_chemical_name_systematic
;
3-[2-(4-Methylphenyl)ethynyl]-2H-chromen-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4695(2)
_cell_length_b                   10.6759(2)
_cell_length_c                   14.5208(2)
_cell_measurement_reflns_used    3107
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0643
_cell_measurement_theta_min      3.0714
_cell_volume                     1299.89(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR2014 (Burla et al.,  2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Agilent CCD diffratcometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5023
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.257
_diffrn_reflns_theta_min         5.160
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0379
_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)+(0.0605P)²+0.3358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                2416
_reflns_number_total             2664
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5424sup1.cif
_cod_data_source_block           I
_cod_database_code               2240373
_cod_database_fobs_code          2240373
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.820
_shelx_estimated_absorpt_t_max   0.875
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
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'
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
O O1 0.13803(10) 0.67272(7) 0.66818(5) 0.0210(2) Uani d 1
O O2 0.15964(12) 0.72775(8) 0.52430(6) 0.0313(2) Uani d 1
C C1 0.16397(14) 0.64322(11) 0.57962(7) 0.0211(2) Uani d 1
C C2 0.19557(13) 0.51127(11) 0.56003(7) 0.0199(2) Uani d 1
C C3 0.18389(13) 0.42253(10) 0.62585(7) 0.0199(2) Uani d 1
H H3 0.1980 0.3368 0.6115 0.024 Uiso calc 1
C C4 0.15055(13) 0.45668(10) 0.71666(7) 0.0184(2) Uani d 1
C C5 0.14038(13) 0.36959(11) 0.78810(8) 0.0206(2) Uani d 1
H H5 0.1504 0.2826 0.7763 0.025 Uiso calc 1
C C6 0.11585(13) 0.40976(11) 0.87544(8) 0.0217(2) Uani d 1
H H6 0.1078 0.3504 0.9233 0.026 Uiso calc 1
C C7 0.10299(13) 0.53744(11) 0.89331(7) 0.0213(2) Uani d 1
H H7 0.0880 0.5645 0.9538 0.026 Uiso calc 1
C C8 0.11176(13) 0.62546(11) 0.82380(7) 0.0204(2) Uani d 1
H H8 0.1033 0.7124 0.8360 0.025 Uiso calc 1
C C9 0.13313(13) 0.58337(10) 0.73620(7) 0.0181(2) Uani d 1
C C10 0.24056(14) 0.48424(11) 0.47093(8) 0.0219(2) Uani d 1
C C11 0.28627(14) 0.46381(11) 0.39787(8) 0.0213(2) Uani d 1
C C12 0.34093(13) 0.43519(11) 0.31108(7) 0.0191(2) Uani d 1
C C13 0.28464(13) 0.50208(11) 0.23036(8) 0.0214(2) Uani d 1
H H13 0.2132 0.5701 0.2333 0.026 Uiso calc 1
C C14 0.33248(14) 0.46968(12) 0.14599(8) 0.0227(3) Uani d 1
H H14 0.2941 0.5166 0.0919 0.027 Uiso calc 1
C C15 0.43582(13) 0.36949(11) 0.13914(8) 0.0215(2) Uani d 1
C C16 0.49343(14) 0.30434(11) 0.22028(8) 0.0229(2) Uani d 1
H H16 0.5653 0.2366 0.2172 0.027 Uiso calc 1
C C17 0.44814(14) 0.33623(11) 0.30511(8) 0.0218(2) Uani d 1
H H17 0.4897 0.2910 0.3595 0.026 Uiso calc 1
C C18 0.48231(15) 0.32959(13) 0.04694(8) 0.0286(3) Uani d 1
H H18A 0.4267 0.3821 -0.0027 0.043 Uiso calc 1
H H18B 0.4526 0.2417 0.0351 0.043 Uiso calc 1
H H18C 0.5978 0.3390 0.0486 0.043 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'
O O 0.0492 0.0322 '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
C1 O1 C9 122.56(9)
O2 C1 O1 117.33(10)
O2 C1 C2 125.32(10)
O1 C1 C2 117.35(9)
C3 C2 C10 123.44(11)
C3 C2 C1 119.92(10)
C10 C2 C1 116.62(10)
C2 C3 C4 120.84(10)
C2 C3 H3 119.6
C4 C3 H3 119.6
C9 C4 C5 118.20(10)
C9 C4 C3 118.30(10)
C5 C4 C3 123.46(10)
C6 C5 C4 120.34(11)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 119.99(10)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.84(10)
C8 C7 H7 119.6
C6 C7 H7 119.6
C9 C8 C7 118.38(10)
C9 C8 H8 120.8
C7 C8 H8 120.8
O1 C9 C8 117.06(10)
O1 C9 C4 120.72(9)
C8 C9 C4 122.22(10)
C11 C10 C2 176.53(12)
C10 C11 C12 178.19(12)
C13 C12 C17 118.68(10)
C13 C12 C11 120.89(10)
C17 C12 C11 120.39(10)
C14 C13 C12 120.37(11)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 121.24(10)
C13 C14 H14 119.4
C15 C14 H14 119.4
C14 C15 C16 118.05(10)
C14 C15 C18 121.64(11)
C16 C15 C18 120.29(11)
C17 C16 C15 121.42(11)
C17 C16 H16 119.3
C15 C16 H16 119.3
C16 C17 C12 120.21(10)
C16 C17 H17 119.9
C12 C17 H17 119.9
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3713(13)
O1 C9 1.3780(13)
O2 C1 1.2053(14)
C1 C2 1.4691(16)
C2 C3 1.3592(15)
C2 C10 1.4287(15)
C3 C4 1.4339(14)
C3 H3 0.9500
C4 C9 1.3941(15)
C4 C5 1.4048(15)
C5 C6 1.3820(15)
C5 H5 0.9500
C6 C7 1.3946(17)
C6 H6 0.9500
C7 C8 1.3887(16)
C7 H7 0.9500
C8 C9 1.3847(15)
C8 H8 0.9500
C10 C11 1.1995(16)
C11 C12 1.4353(15)
C12 C13 1.3978(16)
C12 C17 1.4036(16)
C13 C14 1.3873(15)
C13 H13 0.9500
C14 C15 1.3945(17)
C14 H14 0.9500
C15 C16 1.3958(16)
C15 C18 1.5090(14)
C16 C17 1.3833(15)
C16 H16 0.9500
C17 H17 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7 O2 4_576 0.95 2.48 3.1425(14) 127
C13 H13 Cg1 3_566 0.95 2.94 3.4416(12) 115
C5 H5 Cg2 4_566 0.95 3.00 3.7780(13) 140
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
C9 O1 C1 O2 177.09(10)
C9 O1 C1 C2 -3.21(15)
O2 C1 C2 C3 -174.34(12)
O1 C1 C2 C3 5.98(16)
O2 C1 C2 C10 6.73(18)
O1 C1 C2 C10 -172.95(10)
C10 C2 C3 C4 175.00(10)
C1 C2 C3 C4 -3.86(17)
C2 C3 C4 C9 -1.08(16)
C2 C3 C4 C5 -178.62(10)
C9 C4 C5 C6 -0.84(16)
C3 C4 C5 C6 176.70(10)
C4 C5 C6 C7 -0.77(17)
C5 C6 C7 C8 1.12(17)
C6 C7 C8 C9 0.18(17)
C1 O1 C9 C8 177.74(10)
C1 O1 C9 C4 -1.71(16)
C7 C8 C9 O1 178.68(9)
C7 C8 C9 C4 -1.88(17)
C5 C4 C9 O1 -178.37(9)
C3 C4 C9 O1 3.95(16)
C5 C4 C9 C8 2.21(16)
C3 C4 C9 C8 -175.47(10)
C17 C12 C13 C14 0.91(16)
C11 C12 C13 C14 -176.91(10)
C12 C13 C14 C15 0.70(17)
C13 C14 C15 C16 -1.63(17)
C13 C14 C15 C18 177.00(11)
C14 C15 C16 C17 0.99(17)
C18 C15 C16 C17 -177.67(10)
C15 C16 C17 C12 0.60(18)
C13 C12 C17 C16 -1.54(17)
C11 C12 C17 C16 176.28(10)
