#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:25:25 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158510.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_7158510
loop_
_publ_author_name
'Zhang, Yaohong'
'Luo, Mengqiang'
'Zhang, Yichan'
'Cheng, Kai'
'Li, Yong'
'Qi, Chenze'
'Shen, Runpu'
'Wang, Hai'
_publ_section_title
;
 CuCl₂·2H₂O/TBHP mediated synthesis of
 β-enaminones via coupling reaction of vinyl azides with
 aldehydes.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1952
_journal_page_last               1957
_journal_paper_doi               10.1039/d1ob02479e
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-08-17 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                97.864(2)
_cell_angle_beta                 108.797(2)
_cell_angle_gamma                103.162(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8259(3)
_cell_length_b                   9.8256(2)
_cell_length_c                   10.8672(3)
_cell_measurement_reflns_used    11380
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      74.1990
_cell_measurement_theta_min      4.3940
_cell_volume                     941.65(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0428
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20561
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.41
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.37791
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            coloreless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.383
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.383
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2913
_reflns_number_gt                2887
_reflns_number_total             3333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob02479e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158510.cif.
;
_cod_original_cell_volume        941.65(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7158510
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78775(15) 0.29709(15) 0.11586(13) 0.0417(5) Uani 1 1 d . . .
O2 O 1.24101(14) 0.18526(14) 0.27215(13) 0.0389(5) Uani 1 1 d . . .
N1 N 1.00379(16) 0.19396(17) 0.25201(14) 0.0325(5) Uani 1 1 d . . .
H1A H 0.9547 0.2459 0.2788 0.039 Uiso 1 1 calc R . .
C1 C 1.21419(18) 0.38813(19) 0.40298(16) 0.0295(5) Uani 1 1 d . . .
C2 C 0.4898(2) 0.2267(2) -0.09330(18) 0.0321(5) Uani 1 1 d . . .
C3 C 1.31505(19) 0.5055(2) 0.39134(17) 0.0326(5) Uani 1 1 d . . .
C4 C 1.15868(19) 0.24738(19) 0.30372(16) 0.0304(5) Uani 1 1 d . . .
C5 C 0.78899(19) 0.05642(19) 0.06208(17) 0.0313(5) Uani 1 1 d . . .
H5A H 0.7322 -0.0332 0.0065 0.038 Uiso 1 1 calc R . .
C6 C 0.91976(19) 0.06434(19) 0.16087(16) 0.0296(5) Uani 1 1 d . . .
C7 C 0.73160(19) 0.17809(19) 0.03715(17) 0.0308(5) Uani 1 1 d . . .
C8 C 0.96802(19) -0.0651(2) 0.18096(17) 0.0322(5) Uani 1 1 d . . .
C9 C 0.3746(2) 0.2043(2) -0.2161(2) 0.0396(5) Uani 1 1 d . . .
H9A H 0.3000 0.2495 -0.2215 0.048 Uiso 1 1 calc R . .
C10 C 0.59948(19) 0.15495(19) -0.08924(16) 0.0307(5) Uani 1 1 d . . .
C11 C 0.9347(2) -0.1780(2) 0.07372(19) 0.0374(5) Uani 1 1 d . . .
H11A H 0.8872 -0.1696 -0.0128 0.045 Uiso 1 1 calc R . .
C12 C 1.1630(2) 0.3969(2) 0.50932(18) 0.0367(5) Uani 1 1 d . . .
H12A H 1.0939 0.3178 0.5145 0.044 Uiso 1 1 calc R . .
C13 C 0.5916(2) 0.0654(2) -0.20355(18) 0.0386(5) Uani 1 1 d . . .
H13A H 0.6643 0.0179 -0.1990 0.046 Uiso 1 1 calc R . .
C14 C 1.04087(19) -0.0799(2) 0.31089(19) 0.0385(5) Uani 1 1 d . . .
H14A H 1.0641 -0.0052 0.3837 0.046 Uiso 1 1 calc R . .
C15 C 1.2147(2) 0.5225(2) 0.60660(19) 0.0436(6) Uani 1 1 d . . .
H15A H 1.1823 0.5278 0.6782 0.052 Uiso 1 1 calc R . .
C16 C 1.3648(2) 0.6324(2) 0.4905(2) 0.0407(5) Uani 1 1 d . . .
H16A H 1.4324 0.7128 0.4853 0.049 Uiso 1 1 calc R . .
C17 C 1.3688(2) 0.5049(2) 0.2766(2) 0.0423(5) Uani 1 1 d . . .
H17A H 1.3260 0.4116 0.2172 0.063 Uiso 1 1 calc R . .
H17B H 1.4764 0.5277 0.3099 0.063 Uiso 1 1 calc R . .
H17C H 1.3385 0.5752 0.2293 0.063 Uiso 1 1 calc R . .
C18 C 1.3147(2) 0.6398(2) 0.59622(19) 0.0421(6) Uani 1 1 d . . .
H18A H 1.3490 0.7249 0.6609 0.051 Uiso 1 1 calc R . .
C19 C 0.4884(2) 0.3186(2) 0.0274(2) 0.0426(6) Uani 1 1 d . . .
H19A H 0.4051 0.3579 0.0021 0.064 Uiso 1 1 calc R . .
H19B H 0.5804 0.3954 0.0667 0.064 Uiso 1 1 calc R . .
H19C H 0.4788 0.2618 0.0909 0.064 Uiso 1 1 calc R . .
C20 C 0.4761(3) 0.0464(2) -0.32431(19) 0.0456(6) Uani 1 1 d . . .
H20A H 0.4711 -0.0132 -0.4008 0.055 Uiso 1 1 calc R . .
C21 C 0.9719(2) -0.3035(2) 0.0951(2) 0.0487(6) Uani 1 1 d . . .
H21A H 0.9485 -0.3788 0.0227 0.058 Uiso 1 1 calc R . .
C22 C 1.0781(2) -0.2043(3) 0.3310(2) 0.0494(6) Uani 1 1 d . . .
H22A H 1.1266 -0.2128 0.4173 0.059 Uiso 1 1 calc R . .
C23 C 0.3682(2) 0.1171(2) -0.3299(2) 0.0467(6) Uani 1 1 d . . .
H23A H 0.2909 0.1056 -0.4107 0.056 Uiso 1 1 calc R . .
C24 C 1.0437(3) -0.3169(3) 0.2236(3) 0.0544(7) Uani 1 1 d . . .
H24A H 1.0685 -0.4008 0.2377 0.065 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'
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
C4 N1 C6 126.26(15) . . ?
C3 C1 C12 121.02(17) . . ?
C3 C1 C4 121.13(16) . . ?
C12 C1 C4 117.84(17) . . ?
C9 C2 C10 117.25(17) . . ?
C9 C2 C19 119.49(16) . . ?
C10 C2 C19 123.21(15) . . ?
C1 C3 C16 117.63(18) . . ?
C1 C3 C17 123.56(17) . . ?
C16 C3 C17 118.77(18) . . ?
O2 C4 N1 123.27(16) . . ?
O2 C4 C1 123.82(15) . . ?
N1 C4 C1 112.91(14) . . ?
C6 C5 C7 124.71(16) . . ?
C5 C6 N1 119.87(16) . . ?
C5 C6 C8 121.16(16) . . ?
N1 C6 C8 118.73(14) . . ?
O1 C7 C5 122.28(14) . . ?
O1 C7 C10 120.19(15) . . ?
C5 C7 C10 117.53(14) . . ?
C11 C8 C14 118.76(17) . . ?
C11 C8 C6 121.05(15) . . ?
C14 C8 C6 120.07(17) . . ?
C23 C9 C2 121.82(17) . . ?
C13 C10 C2 120.86(16) . . ?
C13 C10 C7 118.14(15) . . ?
C2 C10 C7 120.94(15) . . ?
C8 C11 C21 120.38(18) . . ?
C15 C12 C1 120.4(2) . . ?
C20 C13 C10 120.34(18) . . ?
C22 C14 C8 120.45(19) . . ?
C18 C15 C12 119.19(19) . . ?
C18 C16 C3 121.0(2) . . ?
C15 C18 C16 120.80(18) . . ?
C23 C20 C13 119.37(18) . . ?
C24 C21 C11 120.4(2) . . ?
C14 C22 C24 120.52(19) . . ?
C9 C23 C20 120.34(17) . . ?
C22 C24 C21 119.51(19) . . ?
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 C7 1.238(2) . ?
O2 C4 1.221(2) . ?
N1 C4 1.383(2) . ?
N1 C6 1.391(2) . ?
C1 C3 1.389(3) . ?
C1 C12 1.401(3) . ?
C1 C4 1.498(2) . ?
C2 C9 1.394(3) . ?
C2 C10 1.409(2) . ?
C2 C19 1.493(3) . ?
C3 C16 1.404(3) . ?
C3 C17 1.503(3) . ?
C5 C6 1.361(2) . ?
C5 C7 1.455(2) . ?
C6 C8 1.475(2) . ?
C7 C10 1.501(2) . ?
C8 C11 1.389(3) . ?
C8 C14 1.407(2) . ?
C9 C23 1.379(3) . ?
C10 C13 1.390(3) . ?
C11 C21 1.392(3) . ?
C12 C15 1.382(3) . ?
C13 C20 1.387(3) . ?
C14 C22 1.379(3) . ?
C15 C18 1.378(3) . ?
C16 C18 1.388(3) . ?
C20 C23 1.384(3) . ?
C21 C24 1.387(3) . ?
C22 C24 1.387(4) . ?
