#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:45:32 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238221 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/49/1554935.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_1554935
loop_
_publ_author_name
'Liu, Yang'
'Jin, Shiyu'
'Huang, Liping'
'Hu, Youhong'
_publ_section_title
;
 Phase transfer reagent promoted tandem ring-opening and ring-closing
 reactions of unique 3-(1-alkynyl) chromones.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2134
_journal_page_last               2137
_journal_paper_doi               10.1021/acs.orglett.5b00721
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C23 H17 Cl O2'
_chemical_formula_weight         360.82
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/m 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                 93.725(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.353(4)
_cell_length_b                   7.448(3)
_cell_length_c                   12.251(5)
_cell_measurement_reflns_used    1726
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.657
_cell_measurement_theta_min      5.316
_cell_volume                     851.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64668
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0483
_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)+(0.1028P)²+0.0315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                1408
_reflns_number_total             1798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00721_si_002.cif
_cod_data_source_block           cd212162
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        851.7(6)
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               1554935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
Cl1 Cl -0.08169(7) 0.2500 0.94725(6) 0.0900(4) Uani 1 2 d S
O1 O 0.12839(18) 0.2500 0.24279(13) 0.0679(6) Uani 1 2 d S
O2 O 0.56048(15) 0.2500 0.31362(11) 0.0463(4) Uani 1 2 d S
C1 C 0.5371(2) 0.2500 0.50121(16) 0.0389(5) Uani 1 2 d S
C2 C 0.6944(2) 0.2500 0.53339(18) 0.0504(6) Uani 1 2 d S
H2A H 0.7404 0.3560 0.5058 0.061 Uiso 0.50 1 calc PR
H2B H 0.7404 0.1440 0.5058 0.061 Uiso 0.50 1 calc PR
C3 C 0.7014(3) 0.2500 0.65857(18) 0.0526(6) Uani 1 2 d S
H3A H 0.7520 0.3556 0.6867 0.063 Uiso 0.50 1 calc PR
H3B H 0.7520 0.1444 0.6867 0.063 Uiso 0.50 1 calc PR
C4 C 0.5475(2) 0.2500 0.69467(17) 0.0484(6) Uani 1 2 d S
H4A H 0.5297 0.1441 0.7378 0.058 Uiso 0.50 1 calc PR
H4B H 0.5297 0.3559 0.7378 0.058 Uiso 0.50 1 calc PR
C5 C 0.4543(2) 0.2500 0.58963(16) 0.0398(5) Uani 1 2 d S
C6 C 0.3045(2) 0.2500 0.57719(16) 0.0427(5) Uani 1 2 d S
C7 C 0.2368(2) 0.2500 0.47295(17) 0.0453(6) Uani 1 2 d S
C8 C 0.3204(2) 0.2500 0.38043(16) 0.0408(5) Uani 1 2 d S
C9 C 0.4696(2) 0.2500 0.39678(15) 0.0385(5) Uani 1 2 d S
C10 C 0.2570(2) 0.2500 0.26715(17) 0.0447(5) Uani 1 2 d S
C11 C 0.3587(2) 0.2500 0.18230(16) 0.0441(5) Uani 1 2 d S
C12 C 0.5050(2) 0.2500 0.20752(16) 0.0435(5) Uani 1 2 d S
C13 C 0.6019(3) 0.2500 0.12682(19) 0.0585(7) Uani 1 2 d S
H13 H 0.7000 0.2500 0.1451 0.070 Uiso 1 2 calc SR
C14 C 0.5503(3) 0.2500 0.0191(2) 0.0711(9) Uani 1 2 d S
H14 H 0.6142 0.2500 -0.0359 0.085 Uiso 1 2 calc SR
C15 C 0.4046(3) 0.2500 -0.00828(19) 0.0715(9) Uani 1 2 d S
H15 H 0.3712 0.2500 -0.0814 0.086 Uiso 1 2 calc SR
C16 C 0.3107(3) 0.2500 0.07099(19) 0.0613(7) Uani 1 2 d S
H16 H 0.2129 0.2500 0.0517 0.074 Uiso 1 2 calc SR
C17 C 0.2182(2) 0.2500 0.67603(16) 0.0450(5) Uani 1 2 d S
C18 C 0.17361(18) 0.0914(3) 0.71996(13) 0.0552(5) Uani 1 1 d .
H18 H 0.2049 -0.0169 0.6921 0.066 Uiso 1 1 calc R
C19 C 0.08302(19) 0.0898(3) 0.80479(13) 0.0608(5) Uani 1 1 d .
H19 H 0.0530 -0.0181 0.8340 0.073 Uiso 1 1 calc R
C20 C 0.0386(2) 0.2500 0.84463(18) 0.0561(7) Uani 1 2 d S
C21 C 0.0754(3) 0.2500 0.4597(2) 0.0678(8) Uani 1 2 d S
H21A H 0.0372 0.2228 0.5287 0.102 Uiso 0.50 1 calc PR
H21B H 0.0440 0.1611 0.4068 0.102 Uiso 0.50 1 calc PR
H21C H 0.0424 0.3662 0.4353 0.102 Uiso 0.50 1 calc PR
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O2 C9 119.44(16) . .
C5 C1 C9 118.71(19) . .
C5 C1 C2 112.80(18) . .
C9 C1 C2 128.48(18) . .
C1 C2 C3 103.93(18) . .
C1 C2 H2A 111.0 . .
C3 C2 H2A 111.0 . .
C1 C2 H2B 111.0 . .
C3 C2 H2B 111.0 . .
H2A C2 H2B 109.0 . .
C2 C3 C4 108.03(18) . .
C2 C3 H3A 110.1 . .
C4 C3 H3A 110.1 . .
C2 C3 H3B 110.1 . .
C4 C3 H3B 110.1 . .
H3A C3 H3B 108.4 . .
C5 C4 C3 104.83(18) . .
C5 C4 H4A 110.8 . .
C3 C4 H4A 110.8 . .
C5 C4 H4B 110.8 . .
C3 C4 H4B 110.8 . .
H4A C4 H4B 108.9 . .
C1 C5 C6 121.79(19) . .
C1 C5 C4 110.41(19) . .
C6 C5 C4 127.80(19) . .
C7 C6 C5 119.57(19) . .
C7 C6 C17 120.42(19) . .
C5 C6 C17 120.00(18) . .
C6 C7 C8 119.6(2) . .
C6 C7 C21 119.49(19) . .
C8 C7 C21 120.9(2) . .
C9 C8 C7 118.87(19) . .
C9 C8 C10 118.20(19) . .
C7 C8 C10 122.93(19) . .
O2 C9 C1 114.71(18) . .
O2 C9 C8 123.81(18) . .
C1 C9 C8 121.48(18) . .
O1 C10 C11 120.38(19) . .
O1 C10 C8 124.1(2) . .
C11 C10 C8 115.52(19) . .
C12 C11 C16 117.7(2) . .
C12 C11 C10 121.62(18) . .
C16 C11 C10 120.7(2) . .
O2 C12 C11 121.42(19) . .
O2 C12 C13 116.92(19) . .
C11 C12 C13 121.7(2) . .
C14 C13 C12 118.7(2) . .
C14 C13 H13 120.7 . .
C12 C13 H13 120.7 . .
C13 C14 C15 120.8(2) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C16 C15 C14 120.1(2) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C15 C16 C11 121.0(2) . .
C15 C16 H16 119.5 . .
C11 C16 H16 119.5 . .
C18 C17 C18 118.6(2) . 4_565
C18 C17 C6 120.64(10) . .
C18 C17 C6 120.64(10) 4_565 .
C17 C18 C19 121.19(17) . .
C17 C18 H18 119.4 . .
C19 C18 H18 119.4 . .
C20 C19 C18 118.49(18) . .
C20 C19 H19 120.8 . .
C18 C19 H19 120.8 . .
C19 C20 C19 122.0(2) . 4_565
C19 C20 Cl1 118.98(10) . .
C19 C20 Cl1 118.98(10) 4_565 .
C7 C21 H21A 109.5 . .
C7 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C7 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C20 1.741(2) .
O1 C10 1.220(3) .
O2 C12 1.368(2) .
O2 C9 1.369(2) .
C1 C5 1.372(3) .
C1 C9 1.390(3) .
C1 C2 1.498(3) .
C2 C3 1.531(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.533(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.507(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.399(3) .
C6 C7 1.388(3) .
C6 C17 1.498(3) .
C7 C8 1.418(3) .
C7 C21 1.508(3) .
C8 C9 1.397(3) .
C8 C10 1.473(3) .
C10 C11 1.455(3) .
C11 C12 1.382(3) .
C11 C16 1.408(3) .
C12 C13 1.384(3) .
C13 C14 1.375(3) .
C13 H13 0.9300 .
C14 C15 1.382(4) .
C14 H14 0.9300 .
C15 C16 1.351(4) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.374(2) .
C17 C18 1.374(2) 4_565
C18 C19 1.383(2) .
C18 H18 0.9300 .
C19 C20 1.364(2) .
C19 H19 0.9300 .
C20 C19 1.364(2) 4_565
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 C1 C2 C3 0.0 . .
C9 C1 C2 C3 180.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C9 C1 C5 C6 0.0 . .
C2 C1 C5 C6 180.0 . .
C9 C1 C5 C4 180.0 . .
C2 C1 C5 C4 0.0 . .
C3 C4 C5 C1 0.0 . .
C3 C4 C5 C6 180.0 . .
C1 C5 C6 C7 0.0 . .
C4 C5 C6 C7 180.0 . .
C1 C5 C6 C17 180.0 . .
C4 C5 C6 C17 0.0 . .
C5 C6 C7 C8 0.0 . .
C17 C6 C7 C8 180.0 . .
C5 C6 C7 C21 180.0 . .
C17 C6 C7 C21 0.0 . .
C6 C7 C8 C9 0.0 . .
C21 C7 C8 C9 180.0 . .
C6 C7 C8 C10 180.0 . .
C21 C7 C8 C10 0.0 . .
C12 O2 C9 C1 180.0 . .
C12 O2 C9 C8 0.0 . .
C5 C1 C9 O2 180.0 . .
C2 C1 C9 O2 0.0 . .
C5 C1 C9 C8 0.0 . .
C2 C1 C9 C8 180.0 . .
C7 C8 C9 O2 180.0 . .
C10 C8 C9 O2 0.0 . .
C7 C8 C9 C1 0.0 . .
C10 C8 C9 C1 180.0 . .
C9 C8 C10 O1 180.0 . .
C7 C8 C10 O1 0.0 . .
C9 C8 C10 C11 0.0 . .
C7 C8 C10 C11 180.0 . .
O1 C10 C11 C12 180.0 . .
C8 C10 C11 C12 0.0 . .
O1 C10 C11 C16 0.0 . .
C8 C10 C11 C16 180.0 . .
C9 O2 C12 C11 0.0 . .
C9 O2 C12 C13 180.0 . .
C16 C11 C12 O2 180.0 . .
C10 C11 C12 O2 0.0 . .
C16 C11 C12 C13 0.0 . .
C10 C11 C12 C13 180.0 . .
O2 C12 C13 C14 180.0 . .
C11 C12 C13 C14 0.0 . .
C12 C13 C14 C15 0.0 . .
C13 C14 C15 C16 0.0 . .
C14 C15 C16 C11 0.0 . .
C12 C11 C16 C15 0.0 . .
C10 C11 C16 C15 180.0 . .
C7 C6 C17 C18 87.72(18) . .
C5 C6 C17 C18 -92.28(18) . .
C7 C6 C17 C18 -87.72(18) . 4_565
C5 C6 C17 C18 92.28(18) . 4_565
C18 C17 C18 C19 1.6(3) 4_565 .
C6 C17 C18 C19 -173.97(17) . .
C17 C18 C19 C20 -0.2(3) . .
C18 C19 C20 C19 -1.3(3) . 4_565
C18 C19 C20 Cl1 177.18(13) . .
