#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:19:29 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157926.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_7157926
loop_
_publ_author_name
'Meng, Ling'
'Chang, Xiaoyong'
'Lin, Zhenyang'
'Wang, Jun Joelle'
_publ_section_title
;
 Metal-free access to 3-allyl-2-alkoxychromanones via phosphine-catalyzed
 alkoxy allylation of chromones with MBH carbonates and alcohols.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2663
_journal_page_last               2667
_journal_paper_doi               10.1039/d1ob00215e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H17 N O6'
_chemical_formula_sum            'C17 H17 N O6'
_chemical_formula_weight         331.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-02 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                84.056(17)
_cell_angle_beta                 84.296(15)
_cell_angle_gamma                84.884(14)
_cell_formula_units_Z            2
_cell_length_a                   7.180(3)
_cell_length_b                   8.862(4)
_cell_length_c                   12.266(6)
_cell_measurement_reflns_used    7488
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.316
_cell_volume                     770.0(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         2.318
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1041 before and 0.0502 after correction. The Ratio of minimum to maximum transmission is 0.9662. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²+0.2547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2904
_reflns_number_total             3549
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00215e2.cif
_cod_data_source_block           cxy0622_0m
_cod_depositor_comments          'Adding full bibliography for 7157926.cif.'
_cod_database_code               7157926
_shelx_shelxl_version_number     2016/6
_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   0.991
_shelx_estimated_absorpt_t_min   0.957
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
O1 O 0.75218(13) 0.37714(10) 0.49532(7) 0.0170(2) Uani 1 1 d . . . . .
O2 O 1.11919(14) -0.05493(10) 0.68677(8) 0.0202(2) Uani 1 1 d . . . . .
O3 O 1.07083(13) 0.19708(10) 0.69766(8) 0.0199(2) Uani 1 1 d . . . . .
O4 O 0.64524(14) 0.15337(10) 0.64650(7) 0.0182(2) Uani 1 1 d . . . . .
O5 O 0.60047(13) 0.46072(10) 0.87498(7) 0.0147(2) Uani 1 1 d . . . . .
O6 O 0.32851(12) 0.34754(10) 0.85191(7) 0.0154(2) Uani 1 1 d . . . . .
C17 C 0.92777(19) -0.10927(15) 0.88838(11) 0.0181(3) Uani 1 1 d . . . . .
H17A H 1.006958 -0.188878 0.857811 0.022 Uiso 1 1 calc R . . . .
H17B H 0.850234 -0.130064 0.954682 0.022 Uiso 1 1 calc R . . . .
N1 N 0.42878(16) -0.04286(13) 0.87208(9) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.79749(19) 0.43965(16) 0.38414(10) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.692910 0.509963 0.360258 0.028 Uiso 1 1 calc GR . . . .
H1B H 0.819594 0.357138 0.335893 0.028 Uiso 1 1 calc GR . . . .
H1C H 0.910925 0.494532 0.380356 0.028 Uiso 1 1 calc GR . . . .
C2 C 0.72010(17) 0.47477(14) 0.57345(10) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.67255(17) 0.41052(14) 0.68264(10) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.64492(17) 0.24838(14) 0.71065(10) 0.0123(2) Uani 1 1 d . . . . .
C5 C 0.61616(17) 0.19927(13) 0.83556(10) 0.0118(2) Uani 1 1 d . . . . .
C6 C 0.80871(17) 0.16273(14) 0.88486(10) 0.0139(3) Uani 1 1 d . . . . .
H6A H 0.880755 0.254032 0.870769 0.017 Uiso 1 1 calc R . . . .
H6B H 0.785860 0.140288 0.965601 0.017 Uiso 1 1 calc R . . . .
C7 C 0.92548(17) 0.03049(14) 0.83864(10) 0.0140(3) Uani 1 1 d . . . . .
C8 C 1.04500(18) 0.06804(14) 0.73442(10) 0.0146(3) Uani 1 1 d . . . . .
C9 C 1.2381(2) -0.02353(17) 0.58620(12) 0.0264(3) Uani 1 1 d . . . . .
H9A H 1.165143 0.038466 0.532027 0.040 Uiso 1 1 calc GR . . . .
H9B H 1.286533 -0.119578 0.556894 0.040 Uiso 1 1 calc GR . . . .
H9C H 1.343395 0.031825 0.601528 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.73346(19) 0.63087(15) 0.55153(11) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.763537 0.673788 0.478350 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7026(2) 0.72335(16) 0.63703(12) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.711873 0.829817 0.621484 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6589(2) 0.66451(15) 0.74422(11) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.639314 0.729107 0.802152 0.023 Uiso 1 1 calc R . . . .
C13 C 0.64417(17) 0.51042(14) 0.76539(10) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.50263(17) 0.32731(14) 0.89427(10) 0.0130(3) Uani 1 1 d . . . . .
H14 H 0.485649 0.296246 0.975137 0.016 Uiso 1 1 calc R . . . .
C15 C 0.20273(19) 0.46167(16) 0.90011(12) 0.0211(3) Uani 1 1 d . . . . .
H15A H 0.183125 0.435331 0.979779 0.032 Uiso 1 1 calc GR . . . .
H15B H 0.082214 0.467613 0.868136 0.032 Uiso 1 1 calc GR . . . .
H15C H 0.256626 0.560328 0.885478 0.032 Uiso 1 1 calc GR . . . .
C16 C 0.50931(17) 0.06326(14) 0.85352(10) 0.0132(3) Uani 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'
N N 0.0061 0.0033 '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
C2 O1 C1 117.56(10) . . ?
C8 O2 C9 114.84(11) . . ?
C13 O5 C14 115.48(9) . . ?
C14 O6 C15 113.90(10) . . ?
H17A C17 H17B 120.0 . . ?
C7 C17 H17A 120.0 . . ?
C7 C17 H17B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.55(11) . . ?
O1 C2 C10 123.16(12) . . ?
C10 C2 C3 120.30(12) . . ?
C2 C3 C4 123.17(11) . . ?
C13 C3 C2 117.14(12) . . ?
C13 C3 C4 119.64(11) . . ?
O4 C4 C3 126.47(12) . . ?
O4 C4 C5 118.92(11) . . ?
C3 C4 C5 114.60(10) . . ?
C4 C5 C6 110.74(10) . . ?
C14 C5 C4 109.60(10) . . ?
C14 C5 C6 109.50(10) . . ?
C16 C5 C4 109.23(10) . . ?
C16 C5 C6 109.41(10) . . ?
C16 C5 C14 108.33(10) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.77(10) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C17 C7 C6 122.65(12) . . ?
C17 C7 C8 121.72(12) . . ?
C8 C7 C6 115.59(11) . . ?
O2 C8 C7 113.09(11) . . ?
O3 C8 O2 123.97(12) . . ?
O3 C8 C7 122.94(11) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10 120.2 . . ?
C11 C10 C2 119.64(13) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.59(13) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.59(12) . . ?
C13 C12 H12 120.7 . . ?
O5 C13 C3 122.35(11) . . ?
C12 C13 O5 114.91(11) . . ?
C12 C13 C3 122.74(12) . . ?
O5 C14 C5 109.16(10) . . ?
O5 C14 H14 109.6 . . ?
O6 C14 O5 112.03(10) . . ?
O6 C14 C5 106.70(10) . . ?
O6 C14 H14 109.6 . . ?
C5 C14 H14 109.6 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C5 176.97(13) . . ?
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
O1 C1 1.4352(16) . ?
O1 C2 1.3462(16) . ?
O2 C8 1.3340(16) . ?
O2 C9 1.4458(17) . ?
O3 C8 1.2083(16) . ?
O4 C4 1.2102(15) . ?
O5 C13 1.3847(16) . ?
O5 C14 1.4158(15) . ?
O6 C14 1.3909(16) . ?
O6 C15 1.4293(16) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C17 C7 1.3223(19) . ?
N1 C16 1.1389(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4213(18) . ?
C2 C10 1.3917(19) . ?
C3 C4 1.4687(18) . ?
C3 C13 1.4031(18) . ?
C4 C5 1.5475(18) . ?
C5 C6 1.5580(18) . ?
C5 C14 1.5356(17) . ?
C5 C16 1.4718(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5051(18) . ?
C7 C8 1.4920(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3749(19) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
O1 C2 C3 C4 -4.43(18) . . . . ?
O1 C2 C3 C13 178.18(11) . . . . ?
O1 C2 C10 C11 -178.45(12) . . . . ?
O4 C4 C5 C6 94.28(13) . . . . ?
O4 C4 C5 C14 -144.81(12) . . . . ?
O4 C4 C5 C16 -26.28(15) . . . . ?
C17 C7 C8 O2 13.37(18) . . . . ?
C17 C7 C8 O3 -166.69(13) . . . . ?
C1 O1 C2 C3 179.03(11) . . . . ?
C1 O1 C2 C10 -1.62(18) . . . . ?
C2 C3 C4 O4 -5.6(2) . . . . ?
C2 C3 C4 C5 173.41(11) . . . . ?
C2 C3 C13 O5 -178.87(11) . . . . ?
C2 C3 C13 C12 0.63(19) . . . . ?
C2 C10 C11 C12 0.1(2) . . . . ?
C3 C2 C10 C11 0.9(2) . . . . ?
C3 C4 C5 C6 -84.81(12) . . . . ?
C3 C4 C5 C14 36.10(14) . . . . ?
C3 C4 C5 C16 154.64(10) . . . . ?
C4 C3 C13 O5 3.63(18) . . . . ?
C4 C3 C13 C12 -176.86(12) . . . . ?
C4 C5 C6 C7 -63.29(14) . . . . ?
C4 C5 C14 O5 -59.06(13) . . . . ?
C4 C5 C14 O6 62.20(12) . . . . ?
C5 C6 C7 C17 -96.45(15) . . . . ?
C5 C6 C7 C8 85.72(14) . . . . ?
C6 C5 C14 O5 62.59(13) . . . . ?
C6 C5 C14 O6 -176.15(10) . . . . ?
C6 C7 C8 O2 -168.77(11) . . . . ?
C6 C7 C8 O3 11.16(18) . . . . ?
C9 O2 C8 O3 0.86(19) . . . . ?
C9 O2 C8 C7 -179.20(12) . . . . ?
C10 C2 C3 C4 176.20(12) . . . . ?
C10 C2 C3 C13 -1.20(18) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 O5 179.80(12) . . . . ?
C11 C12 C13 C3 0.3(2) . . . . ?
C13 O5 C14 O6 -62.11(13) . . . . ?
C13 O5 C14 C5 55.84(13) . . . . ?
C13 C3 C4 O4 171.74(12) . . . . ?
C13 C3 C4 C5 -9.26(16) . . . . ?
C14 O5 C13 C3 -28.37(16) . . . . ?
C14 O5 C13 C12 152.09(11) . . . . ?
C14 C5 C6 C7 175.74(10) . . . . ?
C15 O6 C14 O5 -61.91(13) . . . . ?
C15 O6 C14 C5 178.68(10) . . . . ?
C16 C5 C6 C7 57.16(14) . . . . ?
C16 C5 C14 O5 -178.15(9) . . . . ?
C16 C5 C14 O6 -56.89(13) . . . . ?
