#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512239.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1512239
loop_
_publ_author_name
'Kawade, Rahul Kisan'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold-Catalyzed Oxidative Cyclization of 4-Allenyl-1-ynes with
 8-Methylquinoline Oxide.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4094
_journal_page_last               4097
_journal_paper_doi               10.1021/ol4020199
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C15 H13 Cl O'
_chemical_formula_weight         244.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.8690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1006(7)
_cell_length_b                   9.0852(6)
_cell_length_c                   12.0402(7)
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3658
_cell_measurement_theta_min      2.8088
_cell_volume                     1214.13(13)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9928
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0383P)²+0.4547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2073
_reflns_number_total             2494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4020199_si_002.cif
_cod_data_source_block           mo_121110lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1512239
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.83594(12) 0.39388(15) 0.53129(11) 0.0161(3) Uani 1 1 d .
C2 C 0.92666(13) 0.40410(15) 0.62626(11) 0.0193(3) Uani 1 1 d .
H2A H 0.9167 0.3215 0.6790 0.023 Uiso 1 1 calc R
H2B H 1.0101 0.4031 0.5983 0.023 Uiso 1 1 calc R
C3 C 0.89838(13) 0.54970(16) 0.68098(11) 0.0204(3) Uani 1 1 d .
C4 C 0.79801(13) 0.61985(15) 0.61651(11) 0.0183(3) Uani 1 1 d .
C5 C 0.76506(12) 0.51389(15) 0.52830(11) 0.0172(3) Uani 1 1 d .
H5 H 0.7015 0.5286 0.4758 0.021 Uiso 1 1 calc R
C6 C 0.79994(14) 0.78660(16) 0.60081(13) 0.0237(3) Uani 1 1 d .
H6A H 0.8676 0.8420 0.6352 0.028 Uiso 1 1 calc R
H6B H 0.7704 0.8263 0.5288 0.028 Uiso 1 1 calc R
C7 C 0.70984(14) 0.71971(16) 0.67612(12) 0.0248(3) Uani 1 1 d .
H7A H 0.6246 0.7183 0.6507 0.030 Uiso 1 1 calc R
H7B H 0.7218 0.7340 0.7571 0.030 Uiso 1 1 calc R
C8 C 0.83038(12) 0.26484(15) 0.45814(11) 0.0173(3) Uani 1 1 d .
C9 C 0.74601(12) 0.26556(15) 0.36057(11) 0.0168(3) Uani 1 1 d .
C10 C 0.74116(12) 0.38283(15) 0.28513(11) 0.0179(3) Uani 1 1 d .
H10 H 0.7924 0.4654 0.2964 0.022 Uiso 1 1 calc R
C11 C 0.66277(12) 0.38042(15) 0.19425(11) 0.0190(3) Uani 1 1 d .
H11 H 0.6602 0.4604 0.1434 0.023 Uiso 1 1 calc R
C12 C 0.58836(12) 0.25959(16) 0.17881(11) 0.0197(3) Uani 1 1 d .
C13 C 0.59214(13) 0.14064(16) 0.25037(12) 0.0221(3) Uani 1 1 d .
H13 H 0.5418 0.0576 0.2377 0.026 Uiso 1 1 calc R
C14 C 0.67044(13) 0.14448(15) 0.34081(12) 0.0204(3) Uani 1 1 d .
H14 H 0.6730 0.0633 0.3906 0.024 Uiso 1 1 calc R
C15 C 0.89800(14) 0.14598(17) 0.47921(12) 0.0247(3) Uani 1 1 d .
H15A H 0.9505 0.1444 0.5422 0.030 Uiso 1 1 calc R
H15B H 0.8935 0.0632 0.4312 0.030 Uiso 1 1 calc R
Cl1 Cl 0.48739(3) 0.25821(5) 0.06625(3) 0.02939(13) Uani 1 1 d .
O1 O 0.94740(10) 0.59980(12) 0.76357(8) 0.0281(3) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C1 C8 127.77(12)
C5 C1 C2 110.64(12)
C8 C1 C2 121.57(12)
C3 C2 C1 104.03(11)
C3 C2 H2A 111.0
C1 C2 H2A 111.0
C3 C2 H2B 111.0
C1 C2 H2B 111.0
H2A C2 H2B 109.0
O1 C3 C4 126.00(14)
O1 C3 C2 126.21(13)
C4 C3 C2 107.78(11)
C5 C4 C3 105.72(11)
C5 C4 C7 125.03(12)
C3 C4 C7 119.33(12)
C5 C4 C6 124.20(12)
C3 C4 C6 118.47(12)
C7 C4 C6 58.49(10)
C1 C5 C4 111.79(12)
C1 C5 H5 124.1
C4 C5 H5 124.1
C7 C6 C4 60.60(10)
C7 C6 H6A 117.7
C4 C6 H6A 117.7
C7 C6 H6B 117.7
C4 C6 H6B 117.7
H6A C6 H6B 114.8
C6 C7 C4 60.91(9)
C6 C7 H7A 117.7
C4 C7 H7A 117.7
C6 C7 H7B 117.7
C4 C7 H7B 117.7
H7A C7 H7B 114.8
C15 C8 C1 120.87(13)
C15 C8 C9 119.80(13)
C1 C8 C9 119.32(12)
C10 C9 C14 118.03(13)
C10 C9 C8 122.12(12)
C14 C9 C8 119.83(12)
C11 C10 C9 121.12(13)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 118.94(13)
C12 C11 H11 120.5
C10 C11 H11 120.5
C13 C12 C11 121.58(13)
C13 C12 Cl1 119.43(11)
C11 C12 Cl1 118.98(11)
C12 C13 C14 118.93(13)
C12 C13 H13 120.5
C14 C13 H13 120.5
C13 C14 C9 121.38(13)
C13 C14 H14 119.3
C9 C14 H14 119.3
C8 C15 H15A 120.0
C8 C15 H15B 120.0
H15A C15 H15B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.3447(19)
C1 C8 1.4670(19)
C1 C2 1.5150(18)
C2 C3 1.513(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 O1 1.2148(17)
C3 C4 1.4912(19)
C4 C5 1.4754(19)
C4 C7 1.522(2)
C4 C6 1.5269(19)
C5 H5 0.9500
C6 C7 1.490(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9900
C7 H7B 0.9900
C8 C15 1.337(2)
C8 C9 1.4913(19)
C9 C10 1.4006(19)
C9 C14 1.4015(19)
C10 C11 1.3878(19)
C10 H10 0.9500
C11 C12 1.385(2)
C11 H11 0.9500
C12 C13 1.382(2)
C12 Cl1 1.7456(14)
C13 C14 1.383(2)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9500
C15 H15B 0.9500
