#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152043.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_7152043
loop_
_publ_author_name
'Iaroshenko, Viktor O.'
'Bunescu, Alina'
'Spannenberg, Anke'
'Supe, Linda'
'Milyutina, Maria'
'Langer, Peter'
_publ_section_title
;
 3-Methoxalylchromones - versatile reagents for the regioselective
 synthesis of functionalized 2,4'-dihydroxybenzophenones, potential
 UV-filters.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7554
_journal_page_last               7558
_journal_paper_doi               10.1039/c1ob05931a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C20 H19 Cl O7'
_chemical_formula_weight         406.80
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.519(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7224(3)
_cell_length_b                   8.1879(2)
_cell_length_c                   23.1457(8)
_cell_measurement_reflns_used    6857
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      1.74
_cell_volume                     1834.00(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        X-AREA
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       ω
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30879
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-SHAPE and X-RED32 (Stoe & Cie, 2005)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0303
_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)+(0.0438P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                3277
_reflns_number_total             4380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05931a.txt
_cod_data_source_block           ks1245
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152043
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.76816(12) 0.25564(15) 0.38823(5) 0.0241(2) Uani 1 1 d .
C2 C 0.86717(13) 0.19611(16) 0.43042(5) 0.0286(3) Uani 1 1 d .
H2 H 0.8601 0.2194 0.4702 0.034 Uiso 1 1 calc R
C3 C 0.97539(13) 0.10347(16) 0.41442(6) 0.0291(3) Uani 1 1 d .
H3 H 1.0418 0.0618 0.4435 0.035 Uiso 1 1 calc R
C4 C 0.98911(12) 0.06993(15) 0.35624(6) 0.0266(3) Uani 1 1 d .
H4 H 1.0651 0.0074 0.3456 0.032 Uiso 1 1 calc R
C5 C 0.89153(12) 0.12827(14) 0.31435(5) 0.0234(2) Uani 1 1 d .
H5 H 0.9005 0.1049 0.2747 0.028 Uiso 1 1 calc R
C6 C 0.77861(12) 0.22195(14) 0.32905(5) 0.0213(2) Uani 1 1 d .
C7 C 0.66765(12) 0.27449(14) 0.28576(5) 0.0221(2) Uani 1 1 d .
C8 C 0.66967(12) 0.23368(14) 0.22297(5) 0.0219(2) Uani 1 1 d .
C9 C 0.55434(12) 0.16133(14) 0.19344(5) 0.0208(2) Uani 1 1 d .
C10 C 0.54900(12) 0.13643(14) 0.13308(5) 0.0220(2) Uani 1 1 d .
C11 C 0.65658(13) 0.19864(14) 0.10284(5) 0.0237(2) Uani 1 1 d .
C12 C 0.77209(12) 0.27518(14) 0.13239(5) 0.0230(2) Uani 1 1 d .
C13 C 0.77807(12) 0.28788(14) 0.19202(5) 0.0227(2) Uani 1 1 d .
H13 H 0.8577 0.3346 0.2126 0.027 Uiso 1 1 calc R
C14 C 0.43648(12) 0.11439(14) 0.22741(5) 0.0223(2) Uani 1 1 d .
C15 C 0.20181(13) 0.15484(18) 0.23810(7) 0.0359(3) Uani 1 1 d .
H15A H 0.1755 0.0424 0.2275 0.054 Uiso 1 1 calc R
H15B H 0.1258 0.2288 0.2252 0.054 Uiso 1 1 calc R
H15C H 0.2217 0.1628 0.2803 0.054 Uiso 1 1 calc R
C16 C 0.43573(12) 0.04657(14) 0.09977(5) 0.0234(2) Uani 1 1 d .
C17 C 0.24731(13) -0.13329(16) 0.10103(6) 0.0320(3) Uani 1 1 d .
H17A H 0.1806 -0.0545 0.0829 0.048 Uiso 1 1 calc R
H17B H 0.2022 -0.2018 0.1283 0.048 Uiso 1 1 calc R
H17C H 0.2818 -0.2022 0.0710 0.048 Uiso 1 1 calc R
C18 C 0.88302(13) 0.34492(15) 0.09860(5) 0.0255(2) Uani 1 1 d .
H18A H 0.9406 0.4212 0.1238 0.031 Uiso 1 1 calc R
H18B H 0.8392 0.4080 0.0653 0.031 Uiso 1 1 calc R
C19 C 0.97583(13) 0.21332(16) 0.07611(6) 0.0288(3) Uani 1 1 d .
H19A H 1.0311 0.1625 0.1095 0.035 Uiso 1 1 calc R
H19B H 0.9170 0.1272 0.0565 0.035 Uiso 1 1 calc R
C20 C 1.07235(14) 0.27798(17) 0.03433(6) 0.0324(3) Uani 1 1 d .
H20A H 1.0176 0.3288 0.0008 0.039 Uiso 1 1 calc R
H20B H 1.1253 0.1861 0.0196 0.039 Uiso 1 1 calc R
O1 O 0.66227(10) 0.34201(12) 0.40624(4) 0.0328(2) Uani 1 1 d .
O2 O 0.56691(9) 0.35216(11) 0.30020(4) 0.0297(2) Uani 1 1 d .
O3 O 0.44564(9) 0.01574(11) 0.26599(4) 0.0306(2) Uani 1 1 d .
O4 O 0.32344(8) 0.19975(10) 0.21045(4) 0.02651(19) Uani 1 1 d .
O5 O 0.41410(10) 0.05336(12) 0.04715(4) 0.0321(2) Uani 1 1 d .
O6 O 0.36167(9) -0.04664(11) 0.13185(4) 0.0281(2) Uani 1 1 d .
O7 O 0.65623(10) 0.18862(12) 0.04499(4) 0.0309(2) Uani 1 1 d .
Cl1 Cl 1.19038(4) 0.42576(5) 0.067964(19) 0.05002(12) Uani 1 1 d .
H1 H 0.6091(19) 0.360(2) 0.3744(9) 0.052(5) Uiso 1 1 d .
H7 H 0.580(2) 0.139(2) 0.0306(9) 0.063(6) Uiso 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'
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
O1 C1 C2 117.66(11)
O1 C1 C6 122.10(11)
C2 C1 C6 120.22(11)
C3 C2 C1 119.96(12)
C2 C3 C4 121.02(12)
C5 C4 C3 119.29(12)
C4 C5 C6 121.34(11)
C5 C6 C1 118.17(11)
C5 C6 C7 122.34(11)
C1 C6 C7 119.33(11)
O2 C7 C6 121.00(11)
O2 C7 C8 117.49(10)
C6 C7 C8 121.49(10)
C9 C8 C13 119.64(11)
C9 C8 C7 119.27(10)
C13 C8 C7 120.49(10)
C8 C9 C10 120.08(11)
C8 C9 C14 118.20(10)
C10 C9 C14 121.71(10)
C9 C10 C11 118.84(10)
C9 C10 C16 122.96(10)
C11 C10 C16 118.19(10)
O7 C11 C12 116.00(11)
O7 C11 C10 122.90(11)
C12 C11 C10 121.09(11)
C13 C12 C11 118.38(11)
C13 C12 C18 121.88(11)
C11 C12 C18 119.71(11)
C12 C13 C8 121.72(11)
O3 C14 O4 124.98(11)
O3 C14 C9 123.78(11)
O4 C14 C9 111.21(10)
O5 C16 O6 122.42(11)
O5 C16 C10 123.19(11)
O6 C16 C10 114.35(10)
C12 C18 C19 112.69(10)
C20 C19 C18 113.28(11)
C19 C20 Cl1 111.75(9)
C14 O4 C15 115.08(10)
C16 O6 C17 116.06(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3476(15)
C1 C2 1.3916(17)
C1 C6 1.4105(16)
C2 C3 1.3764(19)
C3 C4 1.3932(18)
C4 C5 1.3752(17)
C5 C6 1.4076(17)
C6 C7 1.4646(16)
C7 O2 1.2403(14)
C7 C8 1.4932(16)
C8 C9 1.3885(16)
C8 C13 1.4022(17)
C9 C10 1.4080(16)
C9 C14 1.5008(16)
C10 C11 1.4086(17)
C10 C16 1.4781(16)
C11 O7 1.3412(14)
C11 C12 1.4050(17)
C12 C13 1.3797(17)
C12 C18 1.5045(17)
C14 O3 1.2009(14)
C14 O4 1.3295(14)
C15 O4 1.4453(15)
C16 O5 1.2173(15)
C16 O6 1.3247(15)
C17 O6 1.4477(15)
C18 C19 1.5285(17)
C19 C20 1.5068(18)
C20 Cl1 1.7931(14)
