#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:35:08 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/05/1570526.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_1570526
loop_
_publ_author_name
'Hou, Jingwei'
'Li, Xiaohong'
'Yan, Kaiyu'
'Zhang, Lei'
'Loh, Teck-Peng'
'Xie, Peizhong'
_publ_section_title
;
 Uracil-Cu(i) catalyst: allylation of cyclopropanols with
 Morita-Baylis-Hillman alcohols under water-tolerant conditions.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1143
_journal_page_last               1149
_journal_paper_doi               10.1039/d3sc04890j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-21 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.733(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.9435(14)
_cell_length_b                   5.7917(2)
_cell_length_c                   17.1106(8)
_cell_measurement_reflns_used    6211
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      2.46
_cell_volume                     3281.1(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16677
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.087
_diffrn_reflns_theta_min         2.461
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0916 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9397.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0450
_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)+(0.0366P)²+2.4475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3407
_reflns_number_total             4363
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04890j2.cif
_cod_data_source_block           220815_wq_ngd_hjw_c_158_0m_a
_cod_depositor_comments          'Adding full bibliography for 1570526.cif.'
_cod_database_code               1570526
_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. 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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C18(H18), C15(H15), C16(H16), C1(H1), C17(H17), C3(H3),
 C5(H5), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O2 O 0.40461(3) -0.07822(16) 0.11253(5) 0.0329(2) Uani 1 1 d . . . . .
O1 O 0.31562(3) 0.73858(17) 0.18570(6) 0.0389(2) Uani 1 1 d . . . . .
O3 O 0.46645(3) 0.04725(19) 0.16942(7) 0.0442(3) Uani 1 1 d . . . . .
C13 C 0.42879(3) 0.4923(2) 0.32779(7) 0.0253(2) Uani 1 1 d . . . . .
C12 C 0.43742(3) 0.3234(2) 0.26941(7) 0.0260(2) Uani 1 1 d . . . . .
H12 H 0.464810 0.277154 0.276022 0.031 Uiso 1 1 calc R . . . .
C11 C 0.41108(3) 0.2272(2) 0.20800(7) 0.0245(2) Uani 1 1 d . . . . .
C7 C 0.29133(3) 0.6288(2) 0.13682(7) 0.0267(2) Uani 1 1 d . . . . .
C10 C 0.36595(3) 0.2611(2) 0.18831(7) 0.0254(2) Uani 1 1 d . . . . .
H10A H 0.358194 0.346783 0.232674 0.030 Uiso 1 1 calc R . . . .
H10B H 0.352705 0.107956 0.184637 0.030 Uiso 1 1 calc R . . . .
C14 C 0.40299(3) 0.6797(2) 0.30522(7) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.389803 0.699305 0.250593 0.033 Uiso 1 1 calc R . . . .
C19 C 0.42599(3) 0.0508(2) 0.15832(7) 0.0260(2) Uani 1 1 d . . . . .
C18 C 0.44798(4) 0.4687(2) 0.40847(8) 0.0311(3) Uani 1 1 d . . . . .
H18 H 0.466036 0.343620 0.424749 0.037 Uiso 1 1 calc R . . . .
C15 C 0.39644(4) 0.8373(2) 0.36188(8) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.378892 0.964642 0.345745 0.038 Uiso 1 1 calc R . . . .
C6 C 0.24762(3) 0.6953(2) 0.11919(7) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.35024(3) 0.3922(2) 0.10987(7) 0.0277(3) Uani 1 1 d . . . . .
H9A H 0.363752 0.544520 0.112987 0.033 Uiso 1 1 calc R . . . .
H9B H 0.357391 0.305138 0.065169 0.033 Uiso 1 1 calc R . . . .
C8 C 0.30455(3) 0.4283(2) 0.09210(8) 0.0280(3) Uani 1 1 d . . . . .
H8A H 0.294768 0.454248 0.033854 0.034 Uiso 1 1 calc R . . . .
H8B H 0.291645 0.285529 0.106164 0.034 Uiso 1 1 calc R . . . .
C16 C 0.41523(4) 0.8111(2) 0.44171(8) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.410536 0.919420 0.480347 0.042 Uiso 1 1 calc R . . . .
C1 C 0.21842(4) 0.5792(2) 0.06330(9) 0.0346(3) Uani 1 1 d . . . . .
H1 H 0.225859 0.449214 0.035896 0.041 Uiso 1 1 calc R . . . .
C17 C 0.44096(4) 0.6256(3) 0.46501(8) 0.0361(3) Uani 1 1 d . . . . .
H17 H 0.453799 0.606004 0.519836 0.043 Uiso 1 1 calc R . . . .
C3 C 0.16745(4) 0.8399(3) 0.08717(9) 0.0418(3) Uani 1 1 d . . . . .
H3 H 0.140088 0.889129 0.076203 0.050 Uiso 1 1 calc R . . . .
C5 C 0.23604(4) 0.8847(2) 0.15916(8) 0.0358(3) Uani 1 1 d . . . . .
H5 H 0.255665 0.965028 0.197757 0.043 Uiso 1 1 calc R . . . .
C2 C 0.17849(4) 0.6518(3) 0.04722(10) 0.0419(3) Uani 1 1 d . . . . .
H2 H 0.158725 0.572035 0.008716 0.050 Uiso 1 1 calc R . . . .
C4 C 0.19612(4) 0.9566(3) 0.14300(9) 0.0427(3) Uani 1 1 d . . . . .
H4 H 0.188478 1.086120 0.170344 0.051 Uiso 1 1 calc R . . . .
C20 C 0.48299(4) -0.1378(3) 0.13035(11) 0.0519(4) Uani 1 1 d . . . . .
H20A H 0.473742 -0.122426 0.072154 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.473937 -0.286294 0.147544 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.512557 -0.130583 0.144795 0.078 Uiso 1 1 calc GR . . . .
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
C19 O3 C20 115.86(11) . . ?
C14 C13 C12 122.39(11) . . ?
C14 C13 C18 118.51(11) . . ?
C18 C13 C12 119.08(11) . . ?
C11 C12 C13 127.53(11) . . ?
C12 C11 C10 126.18(11) . . ?
C12 C11 C19 118.75(10) . . ?
C19 C11 C10 114.74(10) . . ?
O1 C7 C6 119.70(11) . . ?
O1 C7 C8 121.16(11) . . ?
C6 C7 C8 119.13(10) . . ?
C11 C10 C9 113.62(10) . . ?
C15 C14 C13 120.47(12) . . ?
O2 C19 O3 122.21(11) . . ?
O2 C19 C11 124.51(11) . . ?
O3 C19 C11 113.28(10) . . ?
C17 C18 C13 120.74(12) . . ?
C16 C15 C14 120.60(13) . . ?
C1 C6 C7 122.60(11) . . ?
C1 C6 C5 118.88(11) . . ?
C5 C6 C7 118.50(11) . . ?
C8 C9 C10 112.59(10) . . ?
C7 C8 C9 113.94(10) . . ?
C15 C16 C17 119.56(12) . . ?
C2 C1 C6 120.47(13) . . ?
C18 C17 C16 120.12(12) . . ?
C2 C3 C4 120.13(13) . . ?
C4 C5 C6 120.49(13) . . ?
C3 C2 C1 120.03(14) . . ?
C3 C4 C5 119.99(14) . . ?
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
O2 C19 1.2032(15) . ?
O1 C7 1.2164(15) . ?
O3 C19 1.3446(14) . ?
O3 C20 1.4410(17) . ?
C13 C12 1.4730(17) . ?
C13 C14 1.3947(17) . ?
C13 C18 1.3972(17) . ?
C12 C11 1.3413(17) . ?
C11 C10 1.5070(15) . ?
C11 C19 1.4875(16) . ?
C7 C6 1.4979(16) . ?
C7 C8 1.5123(17) . ?
C10 C9 1.5323(17) . ?
C14 C15 1.3847(17) . ?
C18 C17 1.3857(19) . ?
C15 C16 1.3827(19) . ?
C6 C1 1.3895(18) . ?
C6 C5 1.3941(18) . ?
C9 C8 1.5276(16) . ?
C16 C17 1.387(2) . ?
C1 C2 1.3877(18) . ?
C3 C2 1.381(2) . ?
C3 C4 1.381(2) . ?
C5 C4 1.3861(19) . ?
