#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229296.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_2229296
loop_
_publ_author_name
'Ali, Qamar'
'Anis, Itrat'
'Raza Shah, M.'
'Ng, Seik Weng'
_publ_section_title
;
 Bis[5-chloro-2-(prop-2-yn-1-yloxy)phenyl]methane
;
_journal_coeditor_code           XU5147
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o530
_journal_paper_doi               10.1107/S1600536811003205
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H14 Cl2 O2'
_chemical_formula_moiety         'C19 H14 Cl2 O2'
_chemical_formula_sum            'C19 H14 Cl2 O2'
_chemical_formula_weight         345.20
_chemical_name_systematic
;
Bis[5-chloro-2-(prop-2-yn-1-yloxy)phenyl]methane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.258(5)
_cell_angle_beta                 71.412(5)
_cell_angle_gamma                64.707(6)
_cell_formula_units_Z            2
_cell_length_a                   8.4844(5)
_cell_length_b                   9.7845(6)
_cell_length_c                   11.2568(6)
_cell_measurement_reflns_used    3298
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1860
_cell_measurement_theta_min      2.3055
_cell_volume                     798.08(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6118
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0454P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2975
_reflns_number_total             3523
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5147.cif
_cod_data_source_block           I
_cod_original_cell_volume        798.08(8)
_cod_database_code               2229296
_cod_database_fobs_code          2229296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.85099(6) 0.23350(5) 0.67998(4) 0.02285(13) Uani d . 1 . .
Cl Cl2 0.50877(6) 0.78470(5) -0.01311(4) 0.02450(13) Uani d . 1 . .
O O1 0.55177(16) 0.77464(14) 0.41682(11) 0.0196(3) Uani d . 1 . .
O O2 1.00711(16) 0.26968(13) 0.18471(11) 0.0182(3) Uani d . 1 . .
C C1 0.3290(3) 1.1163(2) 0.32429(18) 0.0228(4) Uani d D 1 . .
C C2 0.3478(2) 1.0165(2) 0.39167(16) 0.0182(4) Uani d . 1 . .
C C3 0.3745(2) 0.89566(19) 0.47714(16) 0.0175(4) Uani d . 1 . .
H H3A 0.3701 0.9327 0.5584 0.021 Uiso calc R 1 . .
H H3B 0.2769 0.8603 0.4932 0.021 Uiso calc R 1 . .
C C4 0.6114(2) 0.65014(19) 0.48288(15) 0.0158(4) Uani d . 1 . .
C C5 0.5100(2) 0.6355(2) 0.60376(16) 0.0176(4) Uani d . 1 . .
H H5 0.3909 0.7132 0.6444 0.021 Uiso calc R 1 . .
C C6 0.5838(2) 0.5070(2) 0.66444(16) 0.0176(4) Uani d . 1 . .
H H6 0.5161 0.4960 0.7469 0.021 Uiso calc R 1 . .
C C7 0.7568(2) 0.3954(2) 0.60351(16) 0.0176(4) Uani d . 1 . .
C C8 0.8582(2) 0.4087(2) 0.48282(16) 0.0172(4) Uani d . 1 . .
H H8 0.9766 0.3300 0.4425 0.021 Uiso calc R 1 . .
C C9 0.7868(2) 0.5366(2) 0.42099(15) 0.0154(3) Uani d . 1 . .
C C10 0.8966(2) 0.5563(2) 0.29023(15) 0.0161(4) Uani d . 1 . .
H H10A 0.8890 0.6602 0.2891 0.019 Uiso calc R 1 . .
H H10B 1.0276 0.4843 0.2730 0.019 Uiso calc R 1 . .
C C11 0.8327(2) 0.5312(2) 0.18567(15) 0.0151(3) Uani d . 1 . .
C C12 0.7154(2) 0.6527(2) 0.13844(16) 0.0170(4) Uani d . 1 . .
H H12 0.6728 0.7530 0.1729 0.020 Uiso calc R 1 . .
C C13 0.6599(2) 0.6288(2) 0.04161(16) 0.0172(4) Uani d . 1 . .
C C14 0.7199(2) 0.4852(2) -0.01130(16) 0.0178(4) Uani d . 1 . .
H H14 0.6819 0.4705 -0.0783 0.021 Uiso calc R 1 . .
C C15 0.8372(2) 0.3614(2) 0.03478(16) 0.0167(4) Uani d . 1 . .
H H15 0.8794 0.2615 -0.0005 0.020 Uiso calc R 1 . .
C C16 0.8922(2) 0.38484(19) 0.13286(15) 0.0155(3) Uani d . 1 . .
C C17 1.0784(2) 0.1178(2) 0.13135(17) 0.0199(4) Uani d . 1 . .
H H17A 1.1792 0.0504 0.1634 0.024 Uiso calc R 1 . .
H H17B 1.1309 0.1149 0.0389 0.024 Uiso calc R 1 . .
C C18 0.9368(2) 0.0606(2) 0.16123(16) 0.0196(4) Uani d . 1 . .
C C19 0.8221(3) 0.0152(2) 0.18736(17) 0.0232(4) Uani d D 1 . .
H H1 0.317(3) 1.1950(19) 0.2701(17) 0.033(6) Uiso d D 1 . .
H H19 0.729(2) -0.020(3) 0.209(2) 0.039(6) Uiso d D 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C3 . . 117.28(13) ?
C16 O2 C17 . . 117.67(13) ?
C2 C1 H1 . . 178.8(13) ?
C1 C2 C3 . . 177.80(19) ?
O1 C3 C2 . . 106.72(13) ?
O1 C3 H3A . . 110.4 ?
C2 C3 H3A . . 110.4 ?
O1 C3 H3B . . 110.4 ?
C2 C3 H3B . . 110.4 ?
H3A C3 H3B . . 108.6 ?
O1 C4 C9 . . 115.07(14) ?
O1 C4 C5 . . 123.85(15) ?
C9 C4 C5 . . 121.06(16) ?
C6 C5 C4 . . 119.73(16) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C7 C6 C5 . . 119.16(16) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C8 . . 121.46(16) ?
C6 C7 Cl1 . . 119.33(13) ?
C8 C7 Cl1 . . 119.21(14) ?
C9 C8 C7 . . 120.16(16) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C4 . . 118.44(15) ?
C8 C9 C10 . . 121.38(15) ?
C4 C9 C10 . . 120.17(15) ?
C11 C10 C9 . . 114.36(13) ?
C11 C10 H10A . . 108.7 ?
C9 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
C9 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C12 C11 C16 . . 118.08(15) ?
C12 C11 C10 . . 121.02(15) ?
C16 C11 C10 . . 120.89(15) ?
C13 C12 C11 . . 120.63(16) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 121.33(16) ?
C14 C13 Cl2 . . 119.55(14) ?
C12 C13 Cl2 . . 119.12(14) ?
C13 C14 C15 . . 119.11(16) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
C14 C15 C16 . . 119.73(16) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
O2 C16 C15 . . 123.84(16) ?
O2 C16 C11 . . 115.05(15) ?
C15 C16 C11 . . 121.11(16) ?
O2 C17 C18 . . 112.48(14) ?
O2 C17 H17A . . 109.1 ?
C18 C17 H17A . . 109.1 ?
O2 C17 H17B . . 109.1 ?
C18 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.8 ?
C19 C18 C17 . . 178.90(19) ?
C18 C19 H19 . . 179.4(15) ?
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
Cl1 C7 . 1.7518(18) ?
Cl2 C13 . 1.7492(18) ?
O1 C4 . 1.374(2) ?
O1 C3 . 1.435(2) ?
O2 C16 . 1.378(2) ?
O2 C17 . 1.432(2) ?
C1 C2 . 1.183(3) ?
C1 H1 . 0.94(2) ?
C2 C3 . 1.462(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C9 . 1.401(2) ?
C4 C5 . 1.395(2) ?
C5 C6 . 1.389(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.379(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.389(2) ?
C8 C9 . 1.387(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.521(2) ?
C10 C11 . 1.516(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.389(2) ?
C11 C16 . 1.400(2) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.376(3) ?
C14 C15 . 1.394(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.394(2) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.470(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.184(3) ?
C19 H19 . 0.95(2) ?
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
C6 H6 Cg 2_666 0.95 2.60 3.471(2) 153
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
C4 O1 C3 C2 . . . . 176.88(13) ?
C3 O1 C4 C9 . . . . -178.72(14) ?
C3 O1 C4 C5 . . . . 0.0(2) ?
O1 C4 C5 C6 . . . . -178.32(15) ?
C9 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
C5 C6 C7 C8 . . . . -0.2(3) ?
C5 C6 C7 Cl1 . . . . 179.66(13) ?
C6 C7 C8 C9 . . . . 0.5(3) ?
Cl1 C7 C8 C9 . . . . -179.40(12) ?
C7 C8 C9 C4 . . . . -0.3(2) ?
C7 C8 C9 C10 . . . . 178.34(15) ?
O1 C4 C9 C8 . . . . 178.68(14) ?
C5 C4 C9 C8 . . . . -0.1(2) ?
O1 C4 C9 C10 . . . . 0.0(2) ?
C5 C4 C9 C10 . . . . -178.76(15) ?
C8 C9 C10 C11 . . . . 105.02(18) ?
C4 C9 C10 C11 . . . . -76.4(2) ?
C9 C10 C11 C12 . . . . 97.47(18) ?
C9 C10 C11 C16 . . . . -83.30(19) ?
C16 C11 C12 C13 . . . . -0.2(2) ?
C10 C11 C12 C13 . . . . 179.03(15) ?
C11 C12 C13 C14 . . . . -0.5(2) ?
C11 C12 C13 Cl2 . . . . 178.86(12) ?
C12 C13 C14 C15 . . . . 0.8(2) ?
Cl2 C13 C14 C15 . . . . -178.63(13) ?
C13 C14 C15 C16 . . . . -0.2(2) ?
C17 O2 C16 C15 . . . . 2.2(2) ?
C17 O2 C16 C11 . . . . -177.57(14) ?
C14 C15 C16 O2 . . . . 179.79(15) ?
C14 C15 C16 C11 . . . . -0.5(2) ?
C12 C11 C16 O2 . . . . -179.54(14) ?
C10 C11 C16 O2 . . . . 1.2(2) ?
C12 C11 C16 C15 . . . . 0.7(2) ?
C10 C11 C16 C15 . . . . -178.53(15) ?
C16 O2 C17 C18 . . . . -71.59(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656505
