#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:28:52 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062091.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_7062091
loop_
_publ_author_name
'Chen, Li'
'Huang, Huangjiang'
'Luo, Benlong'
'Liu, Jinggong'
'Yang, Shuang'
'Fang, Xinqiang'
_publ_section_title
;
 Catalytic synthesis of seven-membered carbocycles via ring expansion of
 cyclic β-ketoesters
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              41
_journal_page_last               45
_journal_paper_doi               10.1039/D2NJ03473E
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 N0 O3'
_chemical_formula_sum            'C21 H18 N0 O3'
_chemical_formula_weight         318.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.501(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.44830(10)
_cell_length_b                   9.97000(10)
_cell_length_c                   9.7662(2)
_cell_measurement_reflns_used    28096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4560
_cell_measurement_theta_min      4.4640
_cell_volume                     808.48(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33268
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.433
_diffrn_reflns_theta_min         4.479
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_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)+(0.0470P)²+0.0804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3538
_reflns_number_total             3678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03473e2.cif
_cod_data_source_block           20220602CL-2_autored
_cod_depositor_comments
'Adding full bibliography for 7062089--7062092.cif.'
_cod_original_cell_volume        808.48(2)
_cod_database_code               7062091
_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.
;
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
1.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C24(H24), C23(H23), C20(H20), C21(H21), C22(H22),
 C13(H13), C14(H14), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O17 O 0.34242(15) 0.47347(14) 1.02271(14) 0.0241(3) Uani 1 1 d . . . . .
O18 O 0.33867(15) 0.30393(16) 0.40251(15) 0.0291(3) Uani 1 1 d . . . . .
C9 C 0.38018(19) 0.32625(19) 0.5380(2) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.34453(18) 0.39193(18) 0.79575(19) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.1353(2) 0.65041(18) 0.6920(2) 0.0200(4) Uani 1 1 d . . . . .
H11 H 0.073913 0.576024 0.694807 0.024 Uiso 1 1 calc R U . . .
C7 C 0.35154(18) 0.49301(17) 0.70944(19) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.28523(19) 0.62954(18) 0.69875(19) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.28339(18) 0.39749(17) 0.91214(19) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.3722(2) 0.74044(19) 0.6916(2) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.473010 0.727184 0.694041 0.026 Uiso 1 1 calc R U . . .
C2 C 0.62484(19) 0.45762(18) 0.7167(2) 0.0200(4) Uani 1 1 d . . . . .
H2A H 0.670127 0.399083 0.665308 0.024 Uiso 1 1 calc R U . . .
H2B H 0.668053 0.549099 0.722303 0.024 Uiso 1 1 calc R U . . .
C24 C 0.1407(2) 0.25813(18) 1.0210(2) 0.0207(3) Uani 1 1 d . . . . .
H24 H 0.209134 0.294931 1.120853 0.025 Uiso 1 1 calc R U . . .
C19 C 0.15546(19) 0.29928(17) 0.89140(19) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.0257(2) 0.16345(19) 1.0029(2) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.016354 0.134624 1.090984 0.030 Uiso 1 1 calc R U . . .
C3 C 0.68043(19) 0.40647(19) 0.8818(2) 0.0218(4) Uani 1 1 d . . . . .
H3A H 0.799264 0.398447 0.935776 0.026 Uiso 1 1 calc R U . . .
H3B H 0.651411 0.473604 0.938865 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4246(2) 0.26199(17) 0.7912(2) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.385892 0.189466 0.835903 0.022 Uiso 1 1 calc R U . . .
C20 C 0.05223(19) 0.24650(19) 0.7449(2) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.061682 0.274110 0.656480 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6085(2) 0.27151(18) 0.8891(2) 0.0217(4) Uani 1 1 d . . . . .
H4A H 0.638675 0.252322 0.999084 0.026 Uiso 1 1 calc R U . . .
H4B H 0.657538 0.200999 0.853724 0.026 Uiso 1 1 calc R U . . .
C1 C 0.43744(19) 0.46151(18) 0.6148(2) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.408131 0.531277 0.532080 0.021 Uiso 1 1 calc R U . . .
O1 O 0.37818(14) 0.22683(13) 0.62929(15) 0.0223(3) Uani 1 1 d . . . . .
C21 C -0.0645(2) 0.1535(2) 0.7282(2) 0.0255(4) Uani 1 1 d . . . . .
H21 H -0.136623 0.119303 0.627891 0.031 Uiso 1 1 calc R U . . .
C22 C -0.0759(2) 0.11050(19) 0.8571(2) 0.0252(4) Uani 1 1 d . . . . .
H22 H -0.153446 0.044651 0.845875 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1653(2) 0.8893(2) 0.6763(2) 0.0282(4) Uani 1 1 d . . . . .
H13 H 0.124927 0.977671 0.669692 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3131(2) 0.86936(19) 0.6809(2) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.373434 0.943983 0.676739 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0765(2) 0.7801(2) 0.6813(2) 0.0258(4) Uani 1 1 d . . . . .
H12 H -0.024811 0.794019 0.677356 0.031 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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
O18 C9 C1 124.04(18) . . ?
O18 C9 O1 119.50(17) . . ?
O1 C9 C1 116.46(14) . . ?
C7 C6 C16 127.06(16) . . ?
C7 C6 C5 116.86(14) . . ?
C16 C6 C5 115.64(15) . . ?
C12 C11 C10 119.98(17) . . ?
C6 C7 C10 126.24(15) . . ?
C6 C7 C1 115.33(15) . . ?
C10 C7 C1 118.42(15) . . ?
C11 C10 C7 121.58(15) . . ?
C15 C10 C11 119.01(16) . . ?
C15 C10 C7 119.39(14) . . ?
O17 C16 C6 121.09(15) . . ?
O17 C16 C19 121.89(15) . . ?
C19 C16 C6 116.89(14) . . ?
C14 C15 C10 120.74(16) . . ?
C3 C2 C1 113.25(14) . . ?
C23 C24 C19 119.69(17) . . ?
C24 C19 C16 119.58(15) . . ?
C20 C19 C16 120.77(15) . . ?
C20 C19 C24 119.65(16) . . ?
C24 C23 C22 120.45(17) . . ?
C4 C3 C2 114.09(15) . . ?
C6 C5 C4 111.25(14) . . ?
O1 C5 C6 109.87(13) . . ?
O1 C5 C4 110.69(13) . . ?
C21 C20 C19 119.97(16) . . ?
C3 C4 C5 115.00(14) . . ?
C9 C1 C7 108.43(14) . . ?
C9 C1 C2 108.78(13) . . ?
C7 C1 C2 112.83(14) . . ?
C9 O1 C5 116.63(13) . . ?
C22 C21 C20 120.16(17) . . ?
C21 C22 C23 120.04(17) . . ?
C12 C13 C14 120.05(17) . . ?
C15 C14 C13 119.88(17) . . ?
C13 C12 C11 120.32(16) . . ?
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
O17 C16 1.215(2) . ?
O18 C9 1.208(2) . ?
C9 C1 1.512(2) . ?
C9 O1 1.339(2) . ?
C6 C7 1.336(2) . ?
C6 C16 1.502(2) . ?
C6 C5 1.512(2) . ?
C11 C10 1.402(2) . ?
C11 C12 1.391(3) . ?
C7 C10 1.481(2) . ?
C7 C1 1.525(2) . ?
C10 C15 1.399(2) . ?
C16 C19 1.492(2) . ?
C15 C14 1.386(3) . ?
C2 C3 1.526(2) . ?
C2 C1 1.564(2) . ?
C24 C19 1.399(2) . ?
C24 C23 1.386(3) . ?
C19 C20 1.394(2) . ?
C23 C22 1.387(3) . ?
C3 C4 1.524(2) . ?
C5 C4 1.535(2) . ?
C5 O1 1.467(2) . ?
C20 C21 1.390(2) . ?
C21 C22 1.382(3) . ?
C13 C14 1.390(3) . ?
C13 C12 1.389(3) . ?
