#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157801.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_7157801
loop_
_publ_author_name
'Xie, Zhen-Zhen'
'Deng, Zhi-Xiong'
'Zheng, Yu'
'Chen, Yan-Shan'
'Xiao, Jun-An'
'Chen, Kai'
'Xiang, Hao-Yue'
'Yang, Hua'
_publ_section_title
;
 A phosphine-mediated domino sequence of salicylaldehyde with
 but-3-yn-2-one: rapid access to chromanone.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8916
_journal_page_last               8920
_journal_paper_doi               10.1039/d0ob01588a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C15 H12 Cl2 O4'
_chemical_formula_weight         327.12
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2019-08-22 deposited with the CCDC.	2020-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.736(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3742(4)
_cell_length_b                   18.0280(7)
_cell_length_c                   7.5166(3)
_cell_measurement_reflns_used    3386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      1.87
_cell_volume                     1476.02(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12862
_diffrn_reflns_theta_full        27.73
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.451
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0728P)²+0.6017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                2894
_reflns_number_total             3386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01588a2.cif
_cod_data_source_block           ja
_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/data/users/saulius/crontab/automatic-downloads/current/RSC/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 7556 2019-12-06 15:28:31Z antanas 

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         54.52
_cod_original_formula_units_Z            24
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C2.50 H2 Cl0.33 O0.67'
_cod_database_code               7157801
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.63406(6) 0.17057(3) 0.29545(8) 0.0663(2) Uani 1 1 d . . .
Cl1 Cl 0.91126(5) 0.41522(5) 0.32195(10) 0.0791(2) Uani 1 1 d . . .
O3 O 0.43981(12) 0.27499(7) 0.28066(19) 0.0457(3) Uani 1 1 d . . .
C16 C 0.32648(14) 0.39254(9) 0.2248(2) 0.0325(3) Uani 1 1 d . . .
O2 O 0.45458(13) 0.50125(8) 0.2625(3) 0.0625(4) Uani 1 1 d . . .
O1 O 0.22696(14) 0.42532(9) 0.45212(19) 0.0588(4) Uani 1 1 d . . .
C15 C 0.54638(16) 0.30969(10) 0.2889(2) 0.0389(4) Uani 1 1 d . . .
C14 C 0.55791(15) 0.38678(9) 0.2890(2) 0.0366(4) Uani 1 1 d . . .
C13 C 0.44849(15) 0.43443(9) 0.2618(2) 0.0377(4) Uani 1 1 d . . .
C12 C 0.67133(16) 0.41950(11) 0.3003(2) 0.0431(4) Uani 1 1 d . . .
H12A H 0.6791 0.4709 0.3009 0.052 Uiso 1 1 calc R . .
C11 C 0.23867(15) 0.43977(10) 0.3019(2) 0.0395(4) Uani 1 1 d . . .
O4 O 0.09362(15) 0.33631(11) 0.0735(2) 0.0704(5) Uani 1 1 d . . .
C9 C 0.76085(19) 0.29833(13) 0.3088(3) 0.0547(5) Uani 1 1 d . . .
H9A H 0.8290 0.2689 0.3145 0.066 Uiso 1 1 calc R . .
C8 C 0.27401(16) 0.37777(9) 0.0168(2) 0.0362(3) Uani 1 1 d . . .
C7 C 0.77094(17) 0.37507(13) 0.3105(3) 0.0500(5) Uani 1 1 d . . .
C6 C 0.14555(18) 0.34894(11) -0.0426(3) 0.0467(4) Uani 1 1 d . . .
C5 C 0.35405(17) 0.32068(10) 0.3377(3) 0.0422(4) Uani 1 1 d . . .
H5A H 0.3873 0.3327 0.4684 0.051 Uiso 1 1 calc R . .
H5B H 0.2783 0.2934 0.3224 0.051 Uiso 1 1 calc R . .
C4 C 0.64951(19) 0.26612(11) 0.2985(2) 0.0468(4) Uani 1 1 d . . .
C18 C 0.3368(2) 0.38801(13) -0.1049(3) 0.0544(5) Uani 1 1 d D . .
C2 C 0.1744(2) 0.50414(11) 0.1909(3) 0.0540(5) Uani 1 1 d . . .
H2A H 0.1240 0.5282 0.2564 0.081 Uiso 1 1 calc R . .
H2B H 0.1239 0.4870 0.0726 0.081 Uiso 1 1 calc R . .
H2C H 0.2340 0.5387 0.1723 0.081 Uiso 1 1 calc R . .
C1 C 0.0803(3) 0.33857(17) -0.2439(3) 0.0757(7) Uani 1 1 d . . .
H1A H -0.0010 0.3202 -0.2574 0.114 Uiso 1 1 calc R . .
H1B H 0.1246 0.3037 -0.2966 0.114 Uiso 1 1 calc R . .
H1C H 0.0753 0.3852 -0.3071 0.114 Uiso 1 1 calc R . .
H18B H 0.4172(17) 0.4088(13) -0.068(4) 0.070(7) Uiso 1 1 d D . .
H18A H 0.306(2) 0.3770(13) -0.233(2) 0.066(7) Uiso 1 1 d 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'
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
_geom_angle_publ_flag
C15 O3 C5 113.55(14) . . ?
C8 C16 C5 112.17(14) . . ?
C8 C16 C13 109.73(13) . . ?
C5 C16 C13 106.63(13) . . ?
C8 C16 C11 112.03(13) . . ?
C5 C16 C11 108.03(13) . . ?
C13 C16 C11 108.03(13) . . ?
O3 C15 C14 122.99(15) . . ?
O3 C15 C4 118.15(17) . . ?
C14 C15 C4 118.85(17) . . ?
C15 C14 C12 120.32(16) . . ?
C15 C14 C13 120.24(15) . . ?
C12 C14 C13 119.26(16) . . ?
O2 C13 C14 122.34(16) . . ?
O2 C13 C16 122.71(16) . . ?
C14 C13 C16 114.91(14) . . ?
C7 C12 C14 119.32(19) . . ?
C7 C12 H12A 120.3 . . ?
C14 C12 H12A 120.3 . . ?
O1 C11 C2 121.62(17) . . ?
O1 C11 C16 119.37(16) . . ?
C2 C11 C16 118.96(15) . . ?
C4 C9 C7 119.59(17) . . ?
C4 C9 H9A 120.2 . . ?
C7 C9 H9A 120.2 . . ?
C18 C8 C6 121.18(17) . . ?
C18 C8 C16 123.56(17) . . ?
C6 C8 C16 115.26(14) . . ?
C12 C7 C9 121.13(18) . . ?
C12 C7 Cl1 119.55(18) . . ?
C9 C7 Cl1 119.31(15) . . ?
O4 C6 C1 120.3(2) . . ?
O4 C6 C8 119.34(17) . . ?
C1 C6 C8 120.30(19) . . ?
O3 C5 C16 111.63(14) . . ?
O3 C5 H5A 109.3 . . ?
C16 C5 H5A 109.3 . . ?
O3 C5 H5B 109.3 . . ?
C16 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C9 C4 C15 120.79(19) . . ?
C9 C4 Cl2 120.62(15) . . ?
C15 C4 Cl2 118.59(16) . . ?
C8 C18 H18B 121.0(17) . . ?
C8 C18 H18A 123.8(15) . . ?
H18B C18 H18A 115(2) . . ?
C11 C2 H2A 109.5 . . ?
C11 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C11 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C1 H1A 109.5 . . ?
C6 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C6 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C4 1.731(2) . ?
Cl1 C7 1.732(2) . ?
O3 C15 1.349(2) . ?
O3 C5 1.434(2) . ?
C16 C8 1.528(2) . ?
C16 C5 1.531(2) . ?
C16 C13 1.533(2) . ?
C16 C11 1.546(2) . ?
O2 C13 1.207(2) . ?
O1 C11 1.203(2) . ?
C15 C14 1.396(2) . ?
C15 C4 1.396(2) . ?
C14 C12 1.399(2) . ?
C14 C13 1.477(2) . ?
C12 C7 1.371(3) . ?
C12 H12A 0.9300 . ?
C11 C2 1.492(3) . ?
O4 C6 1.208(3) . ?
C9 C4 1.375(3) . ?
C9 C7 1.388(3) . ?
C9 H9A 0.9300 . ?
C8 C18 1.325(3) . ?
C8 C6 1.493(3) . ?
C6 C1 1.493(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C18 H18B 0.954(17) . ?
C18 H18A 0.949(16) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O3 C15 C14 -21.0(2) . . . . ?
C5 O3 C15 C4 158.73(15) . . . . ?
O3 C15 C14 C12 179.13(15) . . . . ?
C4 C15 C14 C12 -0.6(2) . . . . ?
O3 C15 C14 C13 -5.8(2) . . . . ?
C4 C15 C14 C13 174.41(15) . . . . ?
C15 C14 C13 O2 179.34(18) . . . . ?
C12 C14 C13 O2 -5.6(3) . . . . ?
C15 C14 C13 C16 -3.0(2) . . . . ?
C12 C14 C13 C16 172.06(15) . . . . ?
C8 C16 C13 O2 90.1(2) . . . . ?
C5 C16 C13 O2 -148.23(19) . . . . ?
C11 C16 C13 O2 -32.3(2) . . . . ?
C8 C16 C13 C14 -87.55(17) . . . . ?
C5 C16 C13 C14 34.15(19) . . . . ?
C11 C16 C13 C14 150.05(14) . . . . ?
C15 C14 C12 C7 0.3(3) . . . . ?
C13 C14 C12 C7 -174.78(16) . . . . ?
C8 C16 C11 O1 140.43(17) . . . . ?
C5 C16 C11 O1 16.4(2) . . . . ?
C13 C16 C11 O1 -98.59(19) . . . . ?
C8 C16 C11 C2 -42.0(2) . . . . ?
C5 C16 C11 C2 -166.08(16) . . . . ?
C13 C16 C11 C2 78.93(19) . . . . ?
C5 C16 C8 C18 -107.1(2) . . . . ?
C13 C16 C8 C18 11.2(2) . . . . ?
C11 C16 C8 C18 131.20(19) . . . . ?
C5 C16 C8 C6 71.67(18) . . . . ?
C13 C16 C8 C6 -170.01(14) . . . . ?
C11 C16 C8 C6 -50.02(19) . . . . ?
C14 C12 C7 C9 0.3(3) . . . . ?
C14 C12 C7 Cl1 179.28(14) . . . . ?
C4 C9 C7 C12 -0.7(3) . . . . ?
C4 C9 C7 Cl1 -179.59(15) . . . . ?
C18 C8 C6 O4 175.8(2) . . . . ?
C16 C8 C6 O4 -3.0(3) . . . . ?
C18 C8 C6 C1 -6.5(3) . . . . ?
C16 C8 C6 C1 174.69(18) . . . . ?
C15 O3 C5 C16 56.04(19) . . . . ?
C8 C16 C5 O3 58.75(19) . . . . ?
C13 C16 C5 O3 -61.38(18) . . . . ?
C11 C16 C5 O3 -177.29(14) . . . . ?
C7 C9 C4 C15 0.3(3) . . . . ?
C7 C9 C4 Cl2 179.82(14) . . . . ?
O3 C15 C4 C9 -179.46(16) . . . . ?
C14 C15 C4 C9 0.3(3) . . . . ?
O3 C15 C4 Cl2 1.0(2) . . . . ?
C14 C15 C4 Cl2 -179.20(13) . . . . ?
