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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/86/7108615.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_7108615
loop_
_publ_author_name
'Xinfang Xu'
'Peter Y. Zavalij'
'Wenhao Hu'
'Michael P. Doyle'
_publ_section_title
;
 Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of
 styryl diazoacetate with oximes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11522
_journal_paper_doi               10.1039/c2cc36537e
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C12 H12 Cl N O4'
_chemical_formula_weight         269.68
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.478(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.029(5)
_cell_length_b                   5.2953(17)
_cell_length_c                   29.392(10)
_cell_measurement_temperature    150(2)
_cell_volume                     2492.4(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2138
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.8495
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0896
_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)+(0.0400P)²+39.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2234
_reflns_number_gt                1989
_reflns_number_total             2138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36537e.txt
_cod_data_source_block           2280prelim1
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7108615
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.87731(11) 0.1843(3) 0.52390(5) 0.0438(5) Uani 1 1 d .
C1 C 0.8942(4) 0.3997(11) 0.56865(19) 0.0296(13) Uani 1 1 d .
C2 C 0.8434(4) 0.3926(11) 0.60548(19) 0.0312(13) Uani 1 1 d .
H2 H 0.8009 0.2684 0.6071 0.030(16) Uiso 1 1 calc R
C3 C 0.8553(3) 0.5692(11) 0.63998(19) 0.0278(12) Uani 1 1 d .
H3 H 0.8196 0.5693 0.6649 0.042(18) Uiso 1 1 calc R
C4 C 0.9196(3) 0.7472(10) 0.63830(18) 0.0232(11) Uani 1 1 d .
C5 C 0.9715(3) 0.7441(11) 0.60121(19) 0.0287(13) Uani 1 1 d .
H5 H 1.0157 0.8630 0.6000 0.024(14) Uiso 1 1 calc R
C6 C 0.9595(3) 0.5709(12) 0.56638(19) 0.0315(13) Uani 1 1 d .
H6 H 0.9951 0.5690 0.5414 0.046(19) Uiso 1 1 calc R
C7 C 0.9321(3) 0.9487(11) 0.67256(18) 0.0260(12) Uani 1 1 d .
H7 H 0.9781 1.0609 0.6708 0.05(2) Uiso 1 1 calc R
N8 N 0.8814(3) 0.9725(8) 0.70442(15) 0.0246(10) Uani 1 1 d .
O9 O 0.9049(2) 1.1922(7) 0.73068(12) 0.0277(9) Uani 1 1 d .
C10 C 0.8534(3) 1.2378(10) 0.76590(18) 0.0232(11) Uani 1 1 d .
O10 O 0.7975(2) 1.0990(8) 0.77609(13) 0.0302(9) Uani 1 1 d .
C11 C 0.8780(3) 1.4866(10) 0.78724(18) 0.0258(12) Uani 1 1 d .
H11A H 0.8675 1.6232 0.7647 0.018(13) Uiso 1 1 calc R
H11B H 0.9387 1.4844 0.7953 0.040(17) Uiso 1 1 calc R
C12 C 0.8308(3) 1.5434(11) 0.82961(18) 0.0261(12) Uani 1 1 d .
H12A H 0.8434 1.7187 0.8394 0.025(15) Uiso 1 1 calc R
H12B H 0.7701 1.5335 0.8218 0.033(16) Uiso 1 1 calc R
C13 C 0.8507(3) 1.3701(11) 0.86855(18) 0.0282(13) Uani 1 1 d .
O13 O 0.8966(3) 1.1877(8) 0.86771(14) 0.0367(10) Uani 1 1 d .
O14 O 0.8121(3) 1.4364(8) 0.90616(13) 0.0362(10) Uani 1 1 d .
C15 C 0.8245(4) 1.2762(14) 0.9452(2) 0.0421(16) Uani 1 1 d .
H15A H 0.7991 1.1109 0.9388 0.07(2) Uiso 1 1 calc R
H15B H 0.7984 1.3531 0.9714 0.044(19) Uiso 1 1 calc R
H15C H 0.8845 1.2551 0.9521 0.07(2) 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 0.0033 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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.7(5)
C2 C1 Cl1 119.5(4)
C6 C1 Cl1 118.7(4)
C1 C2 C3 119.2(5)
C2 C3 C4 120.5(5)
C3 C4 C5 118.9(5)
C3 C4 C7 122.8(5)
C5 C4 C7 118.2(5)
C6 C5 C4 121.1(5)
C5 C6 C1 118.6(5)
N8 C7 C4 120.2(5)
C7 N8 O9 108.4(4)
C10 O9 N8 113.2(4)
O10 C10 O9 123.9(5)
O10 C10 C11 127.9(5)
O9 C10 C11 108.2(4)
C10 C11 C12 112.6(5)
C13 C12 C11 114.2(5)
O13 C13 O14 121.9(5)
O13 C13 C12 125.7(5)
O14 C13 C12 112.4(5)
C13 O14 C15 116.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.753(6)
C1 C2 1.382(8)
C1 C6 1.388(8)
C2 C3 1.387(8)
C3 C4 1.399(8)
C4 C5 1.399(7)
C4 C7 1.475(7)
C5 C6 1.382(8)
C7 N8 1.272(7)
N8 O9 1.437(6)
O9 C10 1.374(6)
C10 O10 1.206(6)
C10 C11 1.505(8)
C11 C12 1.516(7)
C12 C13 1.491(8)
C13 O13 1.215(7)
C13 O14 1.337(7)
O14 C15 1.433(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182881
