#------------------------------------------------------------------------------
#$Date: 2020-05-27 02:14:20 +0300 (Wed, 27 May 2020) $
#$Revision: 252363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038410.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_4038410
loop_
_publ_author_name
'Castillo, Juan-Carlos'
'Castro-Agudelo, Brian'
'Gálvez, Jaime'
'Carissan, Yannick'
'Rodríguez, Jean'
'Coquerel, Yoann'
_publ_section_title
;
 Periselectivity in the aza-Diels-Alder cycloaddition between
 α-oxoketenes and N-(5-pyrazolyl)imines: a combined experimental and
 theoretical study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00767
_journal_year                    2020
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_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_date             2020-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.487(2)
_cell_angle_beta                 108.498(2)
_cell_angle_gamma                106.224(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7935(2)
_cell_length_b                   8.8102(3)
_cell_length_c                   9.8737(4)
_cell_measurement_reflns_used    5946
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.29
_cell_measurement_wavelength     0.71073
_cell_volume                     510.53(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2554
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.987
_diffrn_reflns_theta_min         2.293
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0563
_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)+(0.1037P)²+0.0846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1954
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00767_si_002.cif
_cod_data_source_block           yo4140cr
_cod_database_code               4038410
_shelx_shelxl_version_number     2016/4
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
;
_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
C1 C 0.1491(3) 0.1847(2) 0.42055(19) 0.0375(4) Uani 1 1 d . . . . .
C2 C 0.2485(3) 0.1985(2) 0.57510(19) 0.0386(4) Uani 1 1 d . . . . .
C3 C 0.4417(4) 0.1583(3) 0.6610(2) 0.0513(5) Uani 1 1 d . . . . .
H3A H 0.574399 0.213091 0.645666 0.062 Uiso 1 1 calc R . . . .
H3B H 0.407608 0.039073 0.631500 0.062 Uiso 1 1 calc R . . . .
C4 C 0.4729(4) 0.2269(3) 0.8267(2) 0.0581(6) Uani 1 1 d . . . . .
H4A H 0.481365 0.142817 0.876135 0.070 Uiso 1 1 calc R . . . .
H4B H 0.610124 0.323842 0.880750 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2720(4) 0.2745(3) 0.8259(2) 0.0560(5) Uani 1 1 d . . . . .
H5A H 0.174334 0.197605 0.856002 0.067 Uiso 1 1 calc R . . . .
H5B H 0.319436 0.386833 0.892079 0.067 Uiso 1 1 calc R . . . .
C6 C 0.1611(3) 0.2618(2) 0.6664(2) 0.0404(4) Uani 1 1 d . . . . .
C7 C -0.1078(3) 0.3065(2) 0.4716(2) 0.0406(4) Uani 1 1 d . . . . .
C8 C -0.0210(3) 0.2371(2) 0.36813(19) 0.0393(4) Uani 1 1 d . . . . .
C9 C -0.1221(3) 0.2271(3) 0.2053(2) 0.0486(5) Uani 1 1 d . . . . .
H9A H -0.253210 0.256661 0.188180 0.058 Uiso 1 1 calc R . . . .
H9B H -0.169831 0.113234 0.142260 0.058 Uiso 1 1 calc R . . . .
C10 C 0.0404(3) 0.3419(3) 0.1594(2) 0.0501(5) Uani 1 1 d . . . . .
H10A H 0.042689 0.454188 0.190957 0.060 Uiso 1 1 calc R . . . .
H10B H -0.011228 0.305396 0.050558 0.060 Uiso 1 1 calc R . . . .
C11 C 0.2773(3) 0.3439(3) 0.2288(2) 0.0469(5) Uani 1 1 d . . . . .
H11A H 0.365052 0.392859 0.177038 0.056 Uiso 1 1 calc R . . . .
H11B H 0.347154 0.412285 0.333742 0.056 Uiso 1 1 calc R . . . .
C12 C 0.2754(3) 0.1728(3) 0.2182(2) 0.0445(5) Uani 1 1 d . . . . .
O1 O -0.0132(2) 0.31144(17) 0.62067(14) 0.0453(4) Uani 1 1 d . . . . .
O2 O -0.2578(2) 0.35889(19) 0.44164(16) 0.0545(4) Uani 1 1 d . . . . .
O3 O 0.2304(2) 0.10766(16) 0.32655(15) 0.0456(4) Uani 1 1 d . . . . .
O4 O 0.3078(3) 0.0853(2) 0.12528(16) 0.0627(5) Uani 1 1 d . . . . .
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
C8 C1 C2 121.93(15) . . ?
C8 C1 O3 122.17(15) . . ?
O3 C1 C2 115.84(15) . . ?
C1 C2 C3 132.12(16) . . ?
C6 C2 C1 116.81(16) . . ?
C6 C2 C3 111.06(16) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.09(16) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 107.92(17) . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C4 C5 H5A 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C6 C5 C4 102.37(16) . . ?
C6 C5 H5A 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C2 C6 C5 114.46(17) . . ?
C2 C6 O1 124.29(16) . . ?
O1 C6 C5 121.26(16) . . ?
O1 C7 C8 117.38(15) . . ?
O2 C7 C8 126.65(17) . . ?
O2 C7 O1 115.96(15) . . ?
C1 C8 C7 119.15(16) . . ?
C1 C8 C9 122.02(15) . . ?
C7 C8 C9 118.83(16) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.61(16) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.09(16) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C10 111.20(18) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
O3 C12 C11 116.78(15) . . ?
O4 C12 C11 126.62(19) . . ?
O4 C12 O3 116.61(18) . . ?
C6 O1 C7 120.33(13) . . ?
C1 O3 C12 120.81(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
C1 C2 1.423(2) . ?
C1 C8 1.353(2) . ?
C1 O3 1.3821(19) . ?
C2 C3 1.497(3) . ?
C2 C6 1.342(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.550(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.480(3) . ?
C6 O1 1.351(2) . ?
C7 C8 1.449(2) . ?
C7 O1 1.392(2) . ?
C7 O2 1.210(2) . ?
C8 C9 1.508(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.530(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.486(3) . ?
C12 O3 1.386(2) . ?
C12 O4 1.194(2) . ?
