#------------------------------------------------------------------------------
#$Date: 2022-07-29 00:55:37 +0300 (Fri, 29 Jul 2022) $
#$Revision: 276983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130438.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_7130438
loop_
_publ_author_name
'Wang, Biao'
'Zhong, Han'
'Tian, Xu'
_publ_section_title
;
 KOtBu-promoted Michael/aldol/ring-opening cascade reaction of
 cyclobutanones with chalcones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03007A
_journal_year                    2022
_chemical_formula_sum            'C30 H32 Cl F O3'
_chemical_formula_weight         495.00
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                105.511(7)
_cell_angle_beta                 106.708(7)
_cell_angle_gamma                93.809(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4244(8)
_cell_length_b                   9.7735(8)
_cell_length_c                   16.0599(13)
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8700
_cell_measurement_theta_min      4.7330
_cell_volume                     1348.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8428
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.250
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0126(7)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0546
_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)+(0.0566P)²+0.0198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3041
_reflns_number_total             4832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03007a2.cif
_cod_data_source_block           exp_11955
_cod_database_code               7130438
_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_min   0.814
_shelx_estimated_absorpt_t_max   0.849
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
Cl1 Cl 0.83564(8) 0.26550(10) 0.30405(5) 0.0790(3) Uani 1 1 d . . . . .
O1 O 0.2848(2) 0.3957(3) 0.21988(13) 0.0784(7) Uani 1 1 d . . . . .
O2 O 0.4722(2) 0.4115(3) 0.34324(12) 0.0762(7) Uani 1 1 d . . . . .
H2 H 0.403750 0.407045 0.364933 0.114 Uiso 1 1 calc R U . . .
O3 O 0.2647(3) 0.4078(3) 0.43024(15) 0.0936(8) Uani 1 1 d . . . . .
F1 F 0.6878(3) 1.0569(2) 0.41979(14) 0.1207(9) Uani 1 1 d . . . . .
C1 C 0.8162(3) 0.2450(3) 0.18928(18) 0.0528(7) Uani 1 1 d . . . . .
C2 C 0.9483(3) 0.2406(3) 0.1694(2) 0.0654(8) Uani 1 1 d . . . . .
H2A H 1.038519 0.252827 0.215679 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9469(4) 0.2179(3) 0.0808(3) 0.0731(9) Uani 1 1 d . . . . .
H3 H 1.036049 0.214595 0.066809 0.088 Uiso 1 1 calc R U . . .
C4 C 0.8134(4) 0.2004(3) 0.0135(2) 0.0675(8) Uani 1 1 d . . . . .
H4A H 0.811468 0.181901 -0.046750 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6807(3) 0.2100(3) 0.03457(19) 0.0545(7) Uani 1 1 d . . . . .
H5 H 0.591705 0.201249 -0.011924 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6770(3) 0.2326(3) 0.12374(17) 0.0467(6) Uani 1 1 d . . . . .
C7 C 0.5262(3) 0.2434(3) 0.14312(17) 0.0444(6) Uani 1 1 d . . . . .
C8 C 0.3982(3) 0.2230(3) 0.05664(17) 0.0480(6) Uani 1 1 d . . . . .
H8 H 0.362805 0.128959 0.019379 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3307(3) 0.3246(3) 0.02792(16) 0.0434(6) Uani 1 1 d . . . . .
C10 C 0.1967(3) 0.2896(3) -0.05517(16) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.1460(3) 0.1503(3) -0.11333(19) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.198008 0.076798 -0.100720 0.077 Uiso 1 1 calc R U . . .
C12 C 0.0203(4) 0.1183(3) -0.1894(2) 0.0733(9) Uani 1 1 d . . . . .
H12 H -0.011313 0.023892 -0.226904 0.088 Uiso 1 1 calc R U . . .
C13 C -0.0583(3) 0.2244(3) -0.2102(2) 0.0656(8) Uani 1 1 d . . . . .
H13 H -0.142212 0.202860 -0.261883 0.079 Uiso 1 1 calc R U . . .
C14 C -0.0114(3) 0.3624(3) -0.1540(2) 0.0626(8) Uani 1 1 d . . . . .
H14 H -0.064269 0.435156 -0.167087 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1142(3) 0.3943(3) -0.07756(19) 0.0560(7) Uani 1 1 d . . . . .
H15 H 0.144152 0.488839 -0.040129 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3824(3) 0.4813(3) 0.08079(16) 0.0498(6) Uani 1 1 d . . . . .
H16A H 0.305020 0.518091 0.105352 0.060 Uiso 1 1 calc R U . . .
H16B H 0.395186 0.533917 0.039430 0.060 Uiso 1 1 calc R U . . .
C17 C 0.5288(3) 0.5091(3) 0.15870(16) 0.0454(6) Uani 1 1 d . . . . .
H17 H 0.608595 0.497927 0.130625 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5355(3) 0.3949(3) 0.20988(16) 0.0442(6) Uani 1 1 d . . . . .
H18 H 0.633144 0.417233 0.257581 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5681(3) 0.6594(3) 0.22599(17) 0.0506(6) Uani 1 1 d . . . . .
C20 C 0.4629(4) 0.7381(3) 0.2488(2) 0.0813(10) Uani 1 1 d . . . . .
H20 H 0.361831 0.701425 0.219243 0.098 Uiso 1 1 calc R U . . .
C21 C 0.5027(5) 0.8714(4) 0.3148(3) 0.0967(13) Uani 1 1 d . . . . .
H21 H 0.429801 0.922159 0.331027 0.116 Uiso 1 1 calc R U . . .
C22 C 0.6471(5) 0.9245(3) 0.3542(2) 0.0796(10) Uani 1 1 d . . . . .
C23 C 0.7566(5) 0.8534(4) 0.3344(2) 0.0940(12) Uani 1 1 d . . . . .
H23 H 0.857060 0.892912 0.363618 0.113 Uiso 1 1 calc R U . . .
C24 C 0.7149(4) 0.7189(3) 0.2686(2) 0.0754(9) Uani 1 1 d . . . . .
H24 H 0.788977 0.668740 0.253583 0.090 Uiso 1 1 calc R U . . .
C25 C 0.4909(3) 0.1220(3) 0.18325(19) 0.0577(7) Uani 1 1 d . . . . .
H25A H 0.390131 0.118864 0.185588 0.087 Uiso 1 1 calc R U . . .
H25B H 0.559586 0.140629 0.243640 0.087 Uiso 1 1 calc R U . . .
H25C H 0.501177 0.031341 0.145310 0.087 Uiso 1 1 calc R U . . .
C26 C 0.4157(3) 0.3997(3) 0.25574(17) 0.0489(6) Uani 1 1 d . . . . .
C27 C 0.1884(8) 0.6232(6) 0.4107(4) 0.168(2) Uani 1 1 d . . . . .
H27A H 0.284593 0.669916 0.415625 0.252 Uiso 1 1 calc R U . . .
H27B H 0.129586 0.694353 0.430128 0.252 Uiso 1 1 calc R U . . .
H27C H 0.137727 0.567709 0.348547 0.252 Uiso 1 1 calc R U . . .
C28 C 0.2078(5) 0.5318(6) 0.4665(3) 0.1192(17) Uani 1 1 d . . . . .
H28A H 0.276170 0.583926 0.526484 0.143 Uiso 1 1 calc R U . . .
H28B H 0.112128 0.503366 0.473223 0.143 Uiso 1 1 calc R U . . .
C29 C 0.2591(6) 0.3016(6) 0.4732(3) 0.1231(16) Uani 1 1 d . . . . .
H29A H 0.159209 0.284320 0.477351 0.148 Uiso 1 1 calc R U . . .
H29B H 0.328995 0.335738 0.534637 0.148 Uiso 1 1 calc R U . . .
C30 C 0.2951(7) 0.1696(6) 0.4256(4) 0.169(2) Uani 1 1 d . . . . .
H30A H 0.252931 0.153084 0.361129 0.254 Uiso 1 1 calc R U . . .
H30B H 0.254607 0.091974 0.442203 0.254 Uiso 1 1 calc R U . . .
H30C H 0.402115 0.175238 0.441549 0.254 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C29 O3 C28 114.2(3) . . ?
C2 C1 C6 123.2(3) . . ?
C2 C1 Cl1 114.3(2) . . ?
C6 C1 Cl1 122.5(2) . . ?
C1 C2 C3 119.8(3) . . ?
C4 C3 C2 119.4(3) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C6 122.0(3) . . ?
C1 C6 C5 115.1(2) . . ?
C1 C6 C7 125.3(2) . . ?
C5 C6 C7 119.7(2) . . ?
C8 C7 C6 111.3(2) . . ?
C8 C7 C25 106.7(2) . . ?
C6 C7 C25 109.8(2) . . ?
C8 C7 C18 108.7(2) . . ?
C6 C7 C18 108.96(19) . . ?
C25 C7 C18 111.4(2) . . ?
C9 C8 C7 127.2(2) . . ?
C8 C9 C10 122.0(2) . . ?
C8 C9 C16 121.1(2) . . ?
C10 C9 C16 116.8(2) . . ?
C15 C10 C11 116.4(2) . . ?
C15 C10 C9 121.6(2) . . ?
C11 C10 C9 122.0(2) . . ?
C12 C11 C10 121.7(3) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 119.0(3) . . ?
C13 C14 C15 120.4(3) . . ?
C14 C15 C10 121.9(3) . . ?
C9 C16 C17 113.5(2) . . ?
C19 C17 C16 115.3(2) . . ?
C19 C17 C18 110.2(2) . . ?
C16 C17 C18 111.9(2) . . ?
C26 C18 C17 111.6(2) . . ?
C26 C18 C7 112.3(2) . . ?
C17 C18 C7 109.64(19) . . ?
C24 C19 C20 117.3(3) . . ?
C24 C19 C17 119.4(3) . . ?
C20 C19 C17 123.3(3) . . ?
C19 C20 C21 121.9(3) . . ?
C22 C21 C20 118.4(3) . . ?
C21 C22 C23 122.9(3) . . ?
C21 C22 F1 118.8(4) . . ?
C23 C22 F1 118.3(4) . . ?
C22 C23 C24 118.1(3) . . ?
C19 C24 C23 121.5(3) . . ?
O1 C26 O2 122.1(3) . . ?
O1 C26 C18 125.8(2) . . ?
O2 C26 C18 112.1(2) . . ?
O3 C28 C27 112.2(4) . . ?
O3 C29 C30 112.4(4) . . ?
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
Cl1 C1 1.753(3) . ?
O1 C26 1.195(3) . ?
O2 C26 1.321(3) . ?
O3 C29 1.396(5) . ?
O3 C28 1.408(4) . ?
F1 C22 1.380(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.400(3) . ?
C2 C3 1.377(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.401(3) . ?
C6 C7 1.543(3) . ?
C7 C8 1.510(3) . ?
C7 C25 1.554(3) . ?
C7 C18 1.559(3) . ?
C8 C9 1.328(3) . ?
C9 C10 1.491(3) . ?
C9 C16 1.507(3) . ?
C10 C15 1.387(4) . ?
C10 C11 1.389(3) . ?
C11 C12 1.382(4) . ?
C12 C13 1.372(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.384(4) . ?
C16 C17 1.523(3) . ?
C17 C19 1.520(3) . ?
C17 C18 1.548(3) . ?
C18 C26 1.511(3) . ?
C19 C24 1.363(4) . ?
C19 C20 1.367(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.326(5) . ?
C22 C23 1.347(5) . ?
C23 C24 1.396(4) . ?
C27 C28 1.410(6) . ?
C29 C30 1.429(6) . ?
