#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:40:08 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/11/7131172.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_7131172
loop_
_publ_author_name
'Sasane, Amit Vijay'
'Liu, Rai-Shung'
_publ_section_title
;
 Catalyst-free diazo cross-coupling to access useful 3(2H)-furanone
 derivatives.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1086
_journal_page_last               1089
_journal_paper_doi               10.1039/d2cc05912f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2cym65
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7637(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.41961(18)
_cell_length_b                   5.65053(12)
_cell_length_c                   19.2947(3)
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3270
_cell_measurement_theta_min      3.9650
_cell_volume                     1218.88(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -35.00   0.50    0.05    --  -59.16 136.00 -16.00   50
  2  ω    -67.00 -42.00   0.50    0.05    --  -59.16 134.00 164.00   50
  3  ω   -106.00 -65.00   0.50    0.05    --  -72.12 136.00 -16.00   82
  4  ω    -89.00 -64.00   0.50    0.05    --  -72.12 134.00 164.00   50
  5  ω    -67.00 -28.00   0.50    0.05    --  -75.04 136.00 -16.00   78
  6  ω     29.00  54.00   0.50    0.05    --   75.69-134.00  97.00   50
  7  ω     43.00  68.00   0.50    0.05    --   75.69-136.00 -81.00   50
  8  ω     37.00  77.00   0.50    0.05    --   83.90-136.00 -81.00   80
  9  ω     38.00  78.00   0.50    0.05    --   83.90-134.00  97.00   80
 10  ω     17.00  43.00   0.50    0.05    --   56.22 -95.00 -60.00   52
 11  ω     37.00  89.00   0.50    0.05    --   56.22  15.00-180.00  104
 12  ω   -106.00 -70.00   0.50    0.05    --  -59.16 -15.00-180.00   72
 13  ω    -67.00 -42.00   0.50    0.05    --  -59.16 -15.00 -30.00   50
 14  ω   -100.00 -74.00   0.50    0.05    --  -59.16 -15.00 -30.00   52
 15  ω    -63.00 -38.00   0.50    0.05    --  -59.16 -15.00-180.00   50
 16  ω    -58.00 -27.00   0.50    0.05    --  -75.04 111.00 -30.00   62
 17  ω   -118.00 -52.00   0.50    0.05    --  -75.04 -15.00  60.00  132
 18  ω     30.00  92.00   0.50    0.05    --   75.69-111.00-150.00  124
 19  ω     37.00  77.00   0.50    0.05    --   75.69 -95.00 120.00   80
 20  ω     43.00  92.00   0.50    0.05    --   83.90 -95.00 -60.00   98
 21  ω     60.00  91.00   0.50    0.05    --   83.90 -95.00  90.00   62
 22  ω     67.00  92.00   0.50    0.05    --   83.90 -95.00-150.00   50
 23  ω     67.00  92.00   0.50    0.05    --   83.90 -95.00  30.00   50
 24  ω     36.00  93.00   0.50    0.05    --   83.90-111.00  30.00  114
 25  ω     66.00  91.00   0.50    0.05    --   83.90 -95.00 -90.00   50
 26  ω     58.00 134.00   0.50    0.05    --   83.90  15.00-150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0338702000
_diffrn_orient_matrix_UB_12      -0.1783031000
_diffrn_orient_matrix_UB_13      -0.0530276000
_diffrn_orient_matrix_UB_21      0.0301705000
_diffrn_orient_matrix_UB_22      0.2062062000
_diffrn_orient_matrix_UB_23      -0.0455630000
_diffrn_orient_matrix_UB_31      0.1301446000
_diffrn_orient_matrix_UB_32      -0.0014090000
_diffrn_orient_matrix_UB_33      0.0419971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8591
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.954
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0345
_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
'w=1/[σ²(Fo²)+(0.0355P)²+0.4606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1997
_reflns_number_total             2167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc05912f2.cif
_cod_data_source_block           220747lt_auto
_cod_depositor_comments
'Adding full bibliography for 7131170--7131173.cif.'
_cod_database_code               7131172
_shelx_shelxl_version_number     2018/3
_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   0.936
_shelx_estimated_absorpt_t_min   0.917
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.059
_oxdiff_exptl_absorpt_empirical_full_min 0.917
loop_
_space_group_symop_operation_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_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
C1 C 0.72007(9) -0.1147(2) 0.09850(6) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.79111(10) 0.0593(2) 0.07635(6) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.802705 0.205897 0.100902 0.022 Uiso 1 1 calc R U . . .
C3 C 0.84502(10) 0.0215(2) 0.01908(6) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.893755 0.141149 0.004971 0.026 Uiso 1 1 calc R U . . .
C4 C 0.82772(10) -0.1916(2) -0.01773(6) 0.0222(3) Uani 1 1 d . . . . .
H4 H 0.863448 -0.217256 -0.057450 0.027 Uiso 1 1 calc R U . . .
C5 C 0.75819(10) -0.3653(2) 0.00400(6) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.746557 -0.511333 -0.020856 0.025 Uiso 1 1 calc R U . . .
C6 C 0.70474(10) -0.3288(2) 0.06212(6) 0.0186(3) Uani 1 1 d . . . . .
H6 H 0.657822 -0.450493 0.076851 0.022 Uiso 1 1 calc R U . . .
C7 C 0.66491(9) -0.0561(2) 0.16281(6) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.56393(10) -0.2253(2) 0.17239(6) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.585704 -0.395228 0.167841 0.022 Uiso 1 1 calc R U . . .
C9 C 0.46116(10) -0.1459(2) 0.11264(6) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.382785 -0.166835 0.126259 0.027 Uiso 1 1 calc R U . . .
H9B H 0.461313 -0.235738 0.068601 0.027 Uiso 1 1 calc R U . . .
C10 C 0.48802(10) 0.1170(2) 0.10328(6) 0.0223(3) Uani 1 1 d . . . . .
H10A H 0.492673 0.150079 0.053529 0.027 Uiso 1 1 calc R U . . .
H10B H 0.424307 0.216889 0.115941 0.027 Uiso 1 1 calc R U . . .
C12 C 0.76347(9) -0.0292(2) 0.22853(6) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.77303(10) 0.1697(2) 0.27173(6) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.715985 0.293633 0.260964 0.023 Uiso 1 1 calc R U . . .
C14 C 0.86588(11) 0.1880(2) 0.33069(6) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.871591 0.324151 0.360077 0.027 Uiso 1 1 calc R U . . .
C15 C 0.95016(10) 0.0090(2) 0.34688(6) 0.0223(3) Uani 1 1 d . . . . .
H15 H 1.013660 0.022693 0.387015 0.027 Uiso 1 1 calc R U . . .
C16 C 0.94113(10) -0.1900(2) 0.30416(6) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.998408 -0.313442 0.315041 0.026 Uiso 1 1 calc R U . . .
C17 C 0.84821(10) -0.2090(2) 0.24533(6) 0.0189(3) Uani 1 1 d . . . . .
H17 H 0.842387 -0.346022 0.216278 0.023 Uiso 1 1 calc R U . . .
O11 O 0.60159(7) 0.16601(14) 0.14990(4) 0.0177(2) Uani 1 1 d . . . . .
O18 O 0.53660(7) -0.17374(16) 0.23974(4) 0.0219(2) Uani 1 1 d . . . . .
H18 H 0.502867 -0.291198 0.253836 0.033 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C2 C1 C7 117.02(10) . . ?
C6 C1 C2 118.63(10) . . ?
C6 C1 C7 124.34(10) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.03(11) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.00(11) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.41(11) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.75(11) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.16(11) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C1 C7 C8 113.80(9) . . ?
C12 C7 C1 109.81(8) . . ?
C12 C7 C8 114.04(9) . . ?
O11 C7 C1 108.73(9) . . ?
O11 C7 C8 101.52(8) . . ?
O11 C7 C12 108.41(9) . . ?
C7 C8 H8 112.4 . . ?
C9 C8 C7 101.84(9) . . ?
C9 C8 H8 112.4 . . ?
O18 C8 C7 106.92(9) . . ?
O18 C8 H8 112.4 . . ?
O18 C8 C9 110.40(9) . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C8 C9 C10 103.34(9) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C9 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
O11 C10 C9 106.71(9) . . ?
O11 C10 H10A 110.4 . . ?
O11 C10 H10B 110.4 . . ?
C13 C12 C7 122.33(10) . . ?
C13 C12 C17 118.93(10) . . ?
C17 C12 C7 118.73(10) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.24(11) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.52(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.58(11) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.02(11) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.71(11) . . ?
C16 C17 H17 119.6 . . ?
C7 O11 C10 107.14(9) . . ?
C8 O18 H18 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
C1 C2 1.3962(16) . ?
C1 C6 1.3916(17) . ?
C1 C7 1.5378(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3868(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3913(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3805(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3971(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.5379(15) . ?
C7 C12 1.5219(15) . ?
C7 O11 1.4446(14) . ?
C8 H8 1.0000 . ?
C8 C9 1.5350(16) . ?
C8 O18 1.4271(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5350(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 O11 1.4464(14) . ?
C12 C13 1.3901(17) . ?
C12 C17 1.3953(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3919(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3874(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3854(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3909(17) . ?
C17 H17 0.9500 . ?
O18 H18 0.8400 . ?
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
C1 C2 C3 C4 0.64(17) . . . . ?
C1 C7 C8 C9 -73.82(11) . . . . ?
C1 C7 C8 O18 170.34(9) . . . . ?
C1 C7 C12 C13 127.29(11) . . . . ?
C1 C7 C12 C17 -51.71(13) . . . . ?
C1 C7 O11 C10 78.86(10) . . . . ?
C2 C1 C6 C5 -1.04(16) . . . . ?
C2 C1 C7 C8 165.23(10) . . . . ?
C2 C1 C7 C12 -65.57(13) . . . . ?
C2 C1 C7 O11 52.89(12) . . . . ?
C2 C3 C4 C5 -0.99(17) . . . . ?
C3 C4 C5 C6 0.34(17) . . . . ?
C4 C5 C6 C1 0.69(17) . . . . ?
C6 C1 C2 C3 0.38(17) . . . . ?
C6 C1 C7 C8 -15.55(15) . . . . ?
C6 C1 C7 C12 113.65(12) . . . . ?
C6 C1 C7 O11 -127.88(11) . . . . ?
C7 C1 C2 C3 179.65(10) . . . . ?
C7 C1 C6 C5 179.75(10) . . . . ?
C7 C8 C9 C10 -28.63(11) . . . . ?
C7 C12 C13 C14 -178.98(10) . . . . ?
C7 C12 C17 C16 178.81(10) . . . . ?
C8 C7 C12 C13 -103.63(12) . . . . ?
C8 C7 C12 C17 77.36(12) . . . . ?
C8 C7 O11 C10 -41.40(10) . . . . ?
C8 C9 C10 O11 4.73(11) . . . . ?
C9 C10 O11 C7 23.26(11) . . . . ?
C12 C7 C8 C9 159.15(9) . . . . ?
C12 C7 C8 O18 43.30(12) . . . . ?
C12 C7 O11 C10 -161.80(8) . . . . ?
C12 C13 C14 C15 0.29(17) . . . . ?
C13 C12 C17 C16 -0.22(16) . . . . ?
C13 C14 C15 C16 -0.40(18) . . . . ?
C14 C15 C16 C17 0.19(17) . . . . ?
C15 C16 C17 C12 0.12(17) . . . . ?
C17 C12 C13 C14 0.02(16) . . . . ?
O11 C7 C8 C9 42.80(10) . . . . ?
O11 C7 C8 O18 -73.04(10) . . . . ?
O11 C7 C12 C13 8.63(14) . . . . ?
O11 C7 C12 C17 -170.37(9) . . . . ?
O18 C8 C9 C10 84.65(11) . . . . ?
