#------------------------------------------------------------------------------
#$Date: 2022-01-27 01:11:30 +0200 (Thu, 27 Jan 2022) $
#$Revision: 272257 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566148.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_1566148
loop_
_publ_author_name
'Maestri, Giovanni'
'Serafino, Andrea'
'Chiminelli, Maurizio'
'Balestri, Davide'
'Marchiò, Luciano'
'Bigi, Franca'
'Maggi, Raimondo'
'Malacria, Max'
_publ_section_title
;
 Dimerizing Cascades of Enallenamides Reveal the Visible-Light- Promoted
 Activation of Cumulated C-C Double Bonds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06719B
_journal_year                    2022
_chemical_formula_moiety         'C19 H16 Cl N O'
_chemical_formula_sum            'C19 H16 Cl N O'
_chemical_formula_weight         309.78
_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             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                102.666(7)
_cell_angle_beta                 94.860(7)
_cell_angle_gamma                105.758(7)
_cell_formula_units_Z            2
_cell_length_a                   5.8886(5)
_cell_length_b                   10.0297(9)
_cell_length_c                   13.4799(11)
_cell_measurement_reflns_used    2476
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.203
_cell_measurement_theta_min      3.401
_cell_volume                     738.69(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 PhotonII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8836
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         3.401
_diffrn_source                   microfocus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1239 before and 0.0801 after correction. The Ratio of minimum to maximum transmission is 0.7627. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0687
_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)+(0.0961P)²+0.2432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1907
_reflns_number_total             2763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06719b2.cif
_cod_data_source_block           cu_as495_f13_rd_0m
_cod_original_cell_volume        738.69(11)
_cod_database_code               1566148
_shelx_shelxl_version_number     2014/7
_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   0.914
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.044) H2(0.047) H12(0.051) H6(0.045) H19(0.046) H15(0.048)
 H17A(0.053) H17B(0.053) H13(0.052) H3(0.046) H7(0.048) H8(0.045) H14(0.052)
 H16(0.047) H10A(0.052) H10B(0.052)
 Fixed X: H5(0.8916) H2(0.069) H12(0.3577) H6(0.6377) H19(1.163) H15(0.6347)
 H17A(0.9868) H17B(1.073) H13(0.4283) H3(0.3231) H7(0.9649) H8(0.5812)
 H14(0.7261) H16(0.5644) H10A(0.577) H10B(0.4901)
 Fixed Y: H5(0.1749) H2(-0.0192) H12(0.2051) H6(0.0847) H19(0.3753)
 H15(0.6714) H17A(0.3757) H17B(0.5412) H13(0.2758) H3(0.0773) H7(0.2064)
 H8(0.2366) H14(0.5017) H16(0.6032) H10A(0.4198) H10B(0.2544)
 Fixed Z: H5(0.8063) H2(0.6902) H12(0.1667) H6(0.9158) H19(0.3216) H15(0.167)
 H17A(0.1003) H17B(0.1634) H13(0.0152) H3(0.5831) H7(0.637) H8(0.5154)
 H14(0.0312) H16(0.3203) H10A(0.4187) H10B(0.3544)
;
_olex2_exptl_crystal_mounting_method CryoLoop
_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
Cl1 Cl 0.14232(17) -0.03587(11) 0.89541(7) 0.0441(3) Uani 1 1 d . . . . .
O1 O 1.1340(5) 0.2825(4) 0.4886(2) 0.0489(8) Uani 1 1 d . . . . .
N1 N 0.8544(5) 0.3366(4) 0.3915(2) 0.0370(7) Uani 1 1 d . . . . .
C4 C 0.6345(6) 0.1370(4) 0.6832(3) 0.0359(8) Uani 1 1 d . . . . .
C5 C 0.7247(6) 0.1371(4) 0.7829(3) 0.0369(8) Uani 1 1 d . . . . .
H5 H 0.8916 0.1749 0.8063 0.044 Uiso 1 1 calc R . . . .
C1 C 0.3319(6) 0.0264(4) 0.8128(3) 0.0353(8) Uani 1 1 d . . . . .
C2 C 0.2355(7) 0.0218(4) 0.7138(3) 0.0393(9) Uani 1 1 d . . . . .
H2 H 0.0690 -0.0192 0.6902 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6243(7) 0.3955(4) 0.2621(3) 0.0392(9) Uani 1 1 d . . . . .
C12 C 0.4729(7) 0.2919(4) 0.1659(3) 0.0421(9) Uani 1 1 d . . . . .
H12 H 0.3577 0.2051 0.1667 0.051 Uiso 1 1 calc R . . . .
C18 C 0.8830(7) 0.4076(4) 0.2435(3) 0.0380(9) Uani 1 1 d . . . . .
C6 C 0.5749(6) 0.0830(4) 0.8481(3) 0.0379(8) Uani 1 1 d . . . . .
H6 H 0.6377 0.0847 0.9158 0.045 Uiso 1 1 calc R . . . .
C19 C 1.0006(6) 0.3741(4) 0.3180(3) 0.0385(9) Uani 1 1 d . . . . .
H19 H 1.1630 0.3753 0.3216 0.046 Uiso 1 1 calc R . . . .
C15 C 0.6437(7) 0.5822(4) 0.1775(3) 0.0402(9) Uani 1 1 d . . . . .
H15 H 0.6347 0.6714 0.1670 0.048 Uiso 1 1 calc R . . . .
C17 C 0.9401(7) 0.4509(5) 0.1474(3) 0.0438(10) Uani 1 1 d . . . . .
H17A H 0.9868 0.3757 0.1003 0.053 Uiso 1 1 calc R . . . .
H17B H 1.0730 0.5412 0.1634 0.053 Uiso 1 1 calc R . . . .
C13 C 0.5130(7) 0.3310(5) 0.0810(3) 0.0437(9) Uani 1 1 d . . . . .
H13 H 0.4283 0.2758 0.0152 0.052 Uiso 1 1 calc R . . . .
C3 C 0.3876(7) 0.0783(4) 0.6504(3) 0.0385(9) Uani 1 1 d . . . . .
H3 H 0.3231 0.0773 0.5831 0.046 Uiso 1 1 calc R . . . .
C9 C 0.9283(6) 0.2871(4) 0.4715(3) 0.0381(9) Uani 1 1 d . . . . .
C7 C 0.8008(7) 0.1965(4) 0.6182(3) 0.0403(9) Uani 1 1 d . . . . .
H7 H 0.9649 0.2064 0.6370 0.048 Uiso 1 1 calc R . . . .
C8 C 0.7412(7) 0.2382(4) 0.5345(3) 0.0374(8) Uani 1 1 d . . . . .
H8 H 0.5812 0.2366 0.5154 0.045 Uiso 1 1 calc R . . . .
C14 C 0.7060(7) 0.4719(5) 0.0968(3) 0.0432(9) Uani 1 1 d . . . . .
H14 H 0.7261 0.5017 0.0312 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6032(6) 0.5439(4) 0.2631(3) 0.0393(9) Uani 1 1 d . . . . .
H16 H 0.5644 0.6032 0.3203 0.047 Uiso 1 1 calc R . . . .
C10 C 0.6132(7) 0.3479(5) 0.3644(3) 0.0435(10) Uani 1 1 d . . . . .
H10A H 0.5770 0.4198 0.4187 0.052 Uiso 1 1 calc R . . . .
H10B H 0.4901 0.2544 0.3544 0.052 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C19 N1 C10 110.7(3) . . ?
C9 N1 C19 122.9(3) . . ?
C9 N1 C10 126.3(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C7 118.9(3) . . ?
C3 C4 C7 123.1(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C2 C1 Cl1 119.2(3) . . ?
C6 C1 Cl1 119.1(3) . . ?
C6 C1 C2 121.7(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C12 C11 C18 104.3(3) . . ?
C12 C11 C16 108.1(3) . . ?
C12 C11 C10 117.8(4) . . ?
C18 C11 C10 103.1(3) . . ?
C16 C11 C18 103.5(3) . . ?
C16 C11 C10 117.9(3) . . ?
C11 C12 H12 122.7 . . ?
C13 C12 C11 114.5(4) . . ?
C13 C12 H12 122.7 . . ?
C19 C18 C11 110.6(3) . . ?
C19 C18 C17 135.5(3) . . ?
C17 C18 C11 113.9(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.6 . . ?
N1 C19 H19 124.2 . . ?
C18 C19 N1 111.6(3) . . ?
C18 C19 H19 124.2 . . ?
C14 C15 H15 122.9 . . ?
C16 C15 H15 122.9 . . ?
C16 C15 C14 114.2(4) . . ?
C18 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C18 C17 C14 106.0(3) . . ?
H17A C17 H17B 108.7 . . ?
C14 C17 H17A 110.5 . . ?
C14 C17 H17B 110.5 . . ?
C12 C13 H13 122.9 . . ?
C12 C13 C14 114.1(4) . . ?
C14 C13 H13 122.9 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
O1 C9 N1 121.7(3) . . ?
O1 C9 C8 123.1(3) . . ?
N1 C9 C8 115.2(3) . . ?
C4 C7 H7 117.3 . . ?
C8 C7 C4 125.5(4) . . ?
C8 C7 H7 117.3 . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C15 C14 C17 105.9(3) . . ?
C15 C14 H14 112.3 . . ?
C17 C14 H14 112.3 . . ?
C13 C14 C15 107.5(3) . . ?
C13 C14 C17 106.1(3) . . ?
C13 C14 H14 112.3 . . ?
C11 C16 H16 123.1 . . ?
C15 C16 C11 113.8(3) . . ?
C15 C16 H16 123.1 . . ?
N1 C10 C11 104.0(3) . . ?
N1 C10 H10A 111.0 . . ?
N1 C10 H10B 111.0 . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
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 1.736(4) . ?
O1 C9 1.229(4) . ?
N1 C19 1.413(4) . ?
N1 C9 1.368(5) . ?
N1 C10 1.477(4) . ?
C4 C5 1.402(5) . ?
C4 C3 1.403(5) . ?
C4 C7 1.463(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.386(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(5) . ?
C11 C12 1.506(6) . ?
C11 C18 1.541(5) . ?
C11 C16 1.524(6) . ?
C11 C10 1.556(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.308(6) . ?
C18 C19 1.325(5) . ?
C18 C17 1.492(5) . ?
C6 H6 0.9500 . ?
C19 H19 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.517(6) . ?
C15 C16 1.315(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C14 1.571(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.512(6) . ?
C3 H3 0.9500 . ?
C9 C8 1.491(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.338(5) . ?
C8 H8 0.9500 . ?
C14 H14 1.0000 . ?
C16 H16 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
