#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:08:45 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060405.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_7060405
loop_
_publ_author_name
'Yerrabelly, Jayaprakash Rao'
'Bathini, Pavan Kumar'
'Yerrabelly, Hemasri'
'Vadapalli, Kishore'
_publ_section_title
;
 Unusual titanium-induced McMurry coupling of
 4-oxo-4H-chromene-2-carbaldehydes enroute to bis-chromones
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4705
_journal_page_last               4709
_journal_paper_doi               10.1039/D0NJ04730A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 O4'
_chemical_formula_sum            'C22 H18 O4'
_chemical_formula_weight         346.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'C -2ac 2'
_space_group_name_H-M_alt        'C 2 e b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-29 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4743(5)
_cell_length_b                   15.2098(8)
_cell_length_c                   14.2562(8)
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.5970
_cell_measurement_theta_min      2.8560
_cell_volume                     1620.68(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0839
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   64.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  -99.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   72.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615 -113.0000  -47.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   64.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  -99.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   37.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615    0.0000 -150.0000 146

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00    2.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega  -96.00  -34.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177 -179.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega    0.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   57.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615  179.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 10 omega   -8.00   92.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7615   77.0000  -30.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0082578000
_diffrn_orient_matrix_UB_12      0.0289539000
_diffrn_orient_matrix_UB_13      -0.0387786000
_diffrn_orient_matrix_UB_21      -0.0076082000
_diffrn_orient_matrix_UB_22      0.0365624000
_diffrn_orient_matrix_UB_23      0.0306586000
_diffrn_orient_matrix_UB_31      0.0941799000
_diffrn_orient_matrix_UB_32      0.0003881000
_diffrn_orient_matrix_UB_33      0.0058223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11806
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.001
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         2.678
_diffrn_source                   'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1427
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0841P)²+5.1342P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2021
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     1.002
_reflns_number_gt                1133
_reflns_number_total             1427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj04730a2.cif
_cod_data_source_block           d-koo2-r
_cod_depositor_comments          'Adding full bibliography for 7060405.cif.'
_cod_original_sg_symbol_Hall     'C -2bc 2'
_cod_original_sg_symbol_H-M      'C 2 c b'
_cod_database_code               7060405
_shelxl_version_number           2013-2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C1_$1
 1.54 with sigma of 0.02
 C5-C6 \\sim C1-C1_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1) = Uanis(C2)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
4.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C7(H7), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z'
'x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1, -z+1/2'
'x+1/2, -y+1, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.5563(9) 0.3973(4) 0.0953(4) 0.0300(14) Uani 1 1 d . . . . .
H11 H 0.5163 0.4282 0.0431 0.036 Uiso 1 1 calc R . . . .
C5 C 0.5376(9) 0.4345(4) 0.1850(4) 0.0328(16) Uani 1 1 d D . . . .
O2 O 0.5849(10) 0.4197(3) 0.3522(3) 0.0598(19) Uani 1 1 d . . . . .
C9 C 0.6330(9) 0.3157(4) 0.0836(4) 0.0307(15) Uani 1 1 d . . . . .
C8 C 0.6918(9) 0.2697(4) 0.1632(4) 0.0348(16) Uani 1 1 d . . . . .
H8 H 0.7429 0.2144 0.1558 0.042 Uiso 1 1 calc R . . . .
O1 O 0.4134(8) 0.5705(3) 0.1319(3) 0.0488(15) Uani 1 1 d . . . . .
C7 C 0.6756(10) 0.3044(4) 0.2519(5) 0.0371(17) Uani 1 1 d . . . . .
H7 H 0.7171 0.2741 0.3041 0.045 Uiso 1 1 calc R . . . .
C10 C 0.6564(10) 0.2771(4) -0.0130(4) 0.0377(17) Uani 1 1 d . . . . .
H10A H 0.7118 0.2204 -0.0081 0.057 Uiso 1 1 calc R . . . .
H10B H 0.7308 0.3152 -0.0499 0.057 Uiso 1 1 calc R . . . .
H10C H 0.5417 0.2712 -0.0426 0.057 Uiso 1 1 calc R . . . .
C6 C 0.5940(11) 0.3877(4) 0.2610(5) 0.042(2) Uani 1 1 d D . . . .
C3 C 0.4551(14) 0.5522(5) 0.2947(5) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.4047 0.6066 0.3086 0.068 Uiso 1 1 calc R . . . .
C2 C 0.518(2) 0.5013(5) 0.3652(5) 0.096(3) Uani 1 1 d . . . . .
C4 C 0.4647(10) 0.5234(4) 0.1979(5) 0.043(2) Uani 1 1 d . . . . .
C1 C 0.515(2) 0.5287(5) 0.4651(5) 0.096(3) Uani 1 1 d D . . . .
H1A H 0.6170 0.5668 0.4747 0.115 Uiso 1 1 calc R . . . .
H1B H 0.4090 0.5650 0.4730 0.115 Uiso 1 1 calc R . . . .
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'
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
C9 C11 C5 121.0(6) . . ?
C11 C5 C4 121.4(6) . . ?
C6 C5 C11 118.8(5) . . ?
C6 C5 C4 119.7(6) . . ?
C2 O2 C6 118.0(6) . . ?
C11 C9 C8 118.7(5) . . ?
C11 C9 C10 120.7(5) . . ?
C8 C9 C10 120.6(5) . . ?
C7 C8 C9 121.6(6) . . ?
C8 C7 C6 117.9(6) . . ?
C5 C6 O2 123.0(6) . . ?
C5 C6 C7 121.9(6) . . ?
O2 C6 C7 115.0(6) . . ?
C2 C3 C4 121.1(7) . . ?
O2 C2 C3 123.6(7) . . ?
O2 C2 C1 113.4(7) . . ?
C3 C2 C1 123.0(7) . . ?
O1 C4 C5 123.4(6) . . ?
O1 C4 C3 122.1(6) . . ?
C3 C4 C5 114.5(6) . . ?
C1 C1 C2 122.5(9) 2_566 . ?
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
C11 C5 1.404(9) . ?
C11 C9 1.377(9) . ?
C5 C6 1.364(9) . ?
C5 C4 1.470(9) . ?
O2 C6 1.389(8) . ?
O2 C2 1.350(9) . ?
C9 C8 1.404(9) . ?
C9 C10 1.507(9) . ?
C8 C7 1.375(9) . ?
O1 C4 1.242(8) . ?
C7 C6 1.411(9) . ?
C3 C2 1.354(12) . ?
C3 C4 1.450(10) . ?
C2 C1 1.485(10) . ?
C1 C1 1.324(12) 2_566 ?
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
C11 C5 C6 O2 178.5(7) . . . . ?
C11 C5 C6 C7 2.1(10) . . . . ?
C11 C5 C4 O1 1.0(11) . . . . ?
C11 C5 C4 C3 -179.7(7) . . . . ?
C11 C9 C8 C7 -0.4(10) . . . . ?
C5 C11 C9 C8 0.3(10) . . . . ?
C5 C11 C9 C10 -178.6(7) . . . . ?
O2 C2 C1 C1 -22.5(15) . . . 2_566 ?
C9 C11 C5 C6 -1.1(9) . . . . ?
C9 C11 C5 C4 176.7(7) . . . . ?
C9 C8 C7 C6 1.3(11) . . . . ?
C8 C7 C6 C5 -2.2(11) . . . . ?
C8 C7 C6 O2 -178.9(7) . . . . ?
C10 C9 C8 C7 178.5(7) . . . . ?
C6 C5 C4 O1 178.8(7) . . . . ?
C6 C5 C4 C3 -1.8(10) . . . . ?
C6 O2 C2 C3 2.2(18) . . . . ?
C6 O2 C2 C1 179.9(9) . . . . ?
C3 C2 C1 C1 155.3(9) . . . 2_566 ?
C2 O2 C6 C5 -0.6(13) . . . . ?
C2 O2 C6 C7 176.0(10) . . . . ?
C2 C3 C4 C5 3.3(14) . . . . ?
C2 C3 C4 O1 -177.4(10) . . . . ?
C4 C5 C6 O2 0.6(11) . . . . ?
C4 C5 C6 C7 -175.8(7) . . . . ?
C4 C3 C2 O2 -3.6(19) . . . . ?
C4 C3 C2 C1 178.8(11) . . . . ?
