#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/96/2019675.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019675
loop_
_publ_author_name
'Liu, Qi'
'Song, Xiu-Qing'
'Yan, Hong'
_publ_section_title
;
 NMR analysis of a series of
 1,2-bis(1-R-5-oxo-2,3-dihydro-1H-pyrrol-4-ylidene)ethanes
 and X-ray crystal structure analysis of the R = mesityl compound
;
_journal_coeditor_code           FN3174
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              965
_journal_page_last               970
_journal_paper_doi               10.1107/S2053229614020099
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C36 H36 N2 O10'
_chemical_formula_moiety         'C36 H36 N2 O10'
_chemical_formula_sum            'C36 H36 N2 O10'
_chemical_formula_weight         656.67
_chemical_name_common
'Tetramethyl 4,4'-(ethane-1,2-diylidene)bis(5-oxo-1-mesityl-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate)'
_chemical_name_systematic
;Tetramethyl
4,4'-(ethane-1,2-diylidene)bis[5-oxo-1-(2,4,6-trimethylphenyl)-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate]
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.74(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4573(17)
_cell_length_b                   19.181(4)
_cell_length_c                   10.936(2)
_cell_measurement_reflns_used    3848
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8864
_cell_measurement_theta_min      2.1236
_cell_volume                     1723.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2013)'
_computing_data_collection       'CrystalClear (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear (Rigaku, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15252
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.236
_refine_ls_extinction_coef       0.035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2013 (Sheldrick, 2013)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1170P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1977
_reflns_number_gt                2339
_reflns_number_total             3376
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3174sup1.cf
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2019675.cif.'
_cod_database_code               2019675
_cod_database_fobs_code          2019675
#BEGIN Tags that were not found in dictionaries:
_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_min   0.983
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
N N1 0.3756(2) 0.40142(8) 0.21264(16) 0.0496(5) Uani d 1
O O1 0.4903(2) 0.25116(9) 0.15631(17) 0.0724(6) Uani d 1
O O2 0.3284(2) 0.24035(9) 0.29003(17) 0.0734(6) Uani d 1
O O3 0.0977(2) 0.23459(8) 0.02489(17) 0.0784(6) Uani d 1
O O4 -0.0493(2) 0.31772(9) -0.09074(19) 0.0950(8) Uani d 1
O O5 0.3207(2) 0.51858(7) 0.17683(15) 0.0628(5) Uani d 1
C C1 0.5194(3) 0.40672(10) 0.31378(19) 0.0456(5) Uani d 1
C C2 0.5018(3) 0.40498(10) 0.4364(2) 0.0477(5) Uani d 1
C C3 0.6427(3) 0.40839(11) 0.5322(2) 0.0544(6) Uani d 1
H H3 0.6339 0.4072 0.6153 0.065 Uiso calc 1
C C4 0.7959(3) 0.41354(11) 0.5081(2) 0.0565(6) Uani d 1
C C5 0.8064(3) 0.41580(12) 0.3842(2) 0.0606(6) Uani d 1
H H5 0.9086 0.4193 0.3670 0.073 Uiso calc 1
C C6 0.6702(3) 0.41303(11) 0.2841(2) 0.0547(6) Uani d 1
C C7 0.3383(3) 0.40062(13) 0.4662(2) 0.0648(7) Uani d 1
H H7A 0.2636 0.4309 0.4108 0.097 Uiso calc 1
H H7B 0.3474 0.4147 0.5518 0.097 Uiso calc 1
H H7C 0.2992 0.3535 0.4551 0.097 Uiso calc 1
C C8 0.9464(3) 0.41689(15) 0.6131(2) 0.0788(9) Uani d 1
H H8A 1.0203 0.4505 0.5929 0.118 Uiso calc 1
H H8B 0.9976 0.3719 0.6241 0.118 Uiso calc 1
H H8C 0.9175 0.4304 0.6895 0.118 Uiso calc 1
C C9 0.6859(4) 0.41629(18) 0.1501(2) 0.0884(9) Uani d 1
H H9A 0.7949 0.4296 0.1487 0.133 Uiso calc 1
H H9B 0.6107 0.4500 0.1044 0.133 Uiso calc 1
H H9C 0.6622 0.3713 0.1115 0.133 Uiso calc 1
C C10 0.3009(3) 0.33985(10) 0.16504(19) 0.0470(5) Uani d 1
C C11 0.1610(3) 0.35221(10) 0.07672(19) 0.0487(6) Uani d 1
C C12 0.1374(2) 0.42707(10) 0.06727(18) 0.0455(5) Uani d 1
C C13 0.2820(3) 0.45818(10) 0.1554(2) 0.0484(5) Uani d 1
C C14 0.3846(3) 0.27156(11) 0.2021(2) 0.0527(6) Uani d 1
C C15 0.3969(5) 0.17247(15) 0.3300(3) 0.1035(12) Uani d 1
H H15A 0.4579 0.1561 0.2721 0.155 Uiso calc 1
H H15B 0.3106 0.1402 0.3318 0.155 Uiso calc 1
H H15C 0.4675 0.1761 0.4126 0.155 Uiso calc 1
C C16 0.0680(3) 0.29476(11) 0.0051(2) 0.0589(7) Uani d 1
C C17 -0.1398(5) 0.26387(17) -0.1710(4) 0.141(2) Uani d 1
H H17A -0.0652 0.2317 -0.1943 0.211 Uiso calc 1
H H17B -0.2063 0.2848 -0.2454 0.211 Uiso calc 1
H H17C -0.2079 0.2395 -0.1264 0.211 Uiso calc 1
C C18 0.0083(3) 0.46328(10) -0.00094(18) 0.0464(5) Uani d 1
H H18 -0.0752 0.4380 -0.0527 0.056 Uiso calc 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C10 N1 C13 . . 109.63(17)
C10 N1 C1 . . 125.24(16)
C13 N1 C1 . . 124.90(17)
C14 O2 C15 . . 116.3(2)
C16 O4 C17 . . 115.3(2)
C2 C1 C6 . . 122.8(2)
C2 C1 N1 . . 118.5(2)
C6 C1 N1 . . 118.67(19)
C1 C2 C3 . . 117.4(2)
C1 C2 C7 . . 122.0(2)
C3 C2 C7 . . 120.6(2)
C4 C3 C2 . . 122.2(2)
C4 C3 H3 . . 118.9
C2 C3 H3 . . 118.9
C5 C4 C3 . . 118.1(2)
C5 C4 C8 . . 120.7(2)
C3 C4 C8 . . 121.3(2)
C4 C5 C6 . . 122.6(2)
C4 C5 H5 . . 118.7
C6 C5 H5 . . 118.7
C5 C6 C1 . . 117.0(2)
C5 C6 C9 . . 121.2(2)
C1 C6 C9 . . 121.9(2)
C2 C7 H7A . . 109.5
C2 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C2 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C4 C8 H8A . . 109.5
C4 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C4 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C6 C9 H9A . . 109.5
C6 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C6 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C11 C10 N1 . . 111.20(17)
C11 C10 C14 . . 128.35(18)
N1 C10 C14 . . 120.07(18)
C10 C11 C12 . . 107.79(17)
C10 C11 C16 . . 120.95(19)
C12 C11 C16 . . 131.16(18)
C18 C12 C11 . . 128.67(19)
C18 C12 C13 . . 125.43(18)
C11 C12 C13 . . 105.81(16)
O5 C13 N1 . . 123.9(2)
O5 C13 C12 . . 130.59(19)
N1 C13 C12 . . 105.51(16)
O1 C14 O2 . . 126.6(2)
O1 C14 C10 . . 121.8(2)
O2 C14 C10 . . 111.5(2)
O2 C15 H15A . . 109.5
O2 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
O2 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
O3 C16 O4 . . 123.2(2)
O3 C16 C11 . . 124.6(2)
O4 C16 C11 . . 112.05(18)
O4 C17 H17A . . 109.5
O4 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
O4 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C12 C18 C18 . 3_565 124.8(2)
C12 C18 H18 . . 117.6
C18 C18 H18 3_565 . 117.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10 . 1.382(3) yes
N1 C13 . 1.403(2) yes
N1 C1 . 1.440(3) yes
O1 C14 . 1.190(3) ?
O2 C14 . 1.314(3) ?
O2 C15 . 1.449(3) ?
O3 C16 . 1.190(3) ?
O4 C16 . 1.335(3) ?
O4 C17 . 1.451(3) ?
O5 C13 . 1.212(2) ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.394(3) ?
C2 C3 . 1.389(3) ?
C2 C7 . 1.496(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(3) ?
C4 C8 . 1.500(3) ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9300 ?
C6 C9 . 1.505(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.359(3) yes
C10 C14 . 1.498(3) yes
C11 C12 . 1.450(3) yes
C11 C16 . 1.468(3) yes
C12 C18 . 1.358(3) yes
C12 C13 . 1.490(3) yes
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C18 3_565 1.416(4) yes
C18 H18 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O5 3_666 0.93 2.63 3.423(3) 143
C8 H8B O3 4_666 0.96 2.55 3.405(3) 148
C17 H17B O1 4_465 0.96 2.63 3.260(5) 124
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C10 N1 C1 C2 . -84.0(3)
C13 N1 C1 C2 . 89.9(2)
C10 N1 C1 C6 . 95.7(3)
C13 N1 C1 C6 . -90.4(3)
C6 C1 C2 C3 . -1.3(3)
N1 C1 C2 C3 . 178.40(18)
C6 C1 C2 C7 . 177.9(2)
N1 C1 C2 C7 . -2.5(3)
C1 C2 C3 C4 . 0.2(3)
C7 C2 C3 C4 . -179.0(2)
C2 C3 C4 C5 . 0.5(3)
C2 C3 C4 C8 . -179.8(2)
C3 C4 C5 C6 . -0.1(3)
C8 C4 C5 C6 . -179.8(2)
C4 C5 C6 C1 . -0.9(3)
C4 C5 C6 C9 . 179.4(2)
C2 C1 C6 C5 . 1.6(3)
N1 C1 C6 C5 . -178.03(19)
C2 C1 C6 C9 . -178.7(2)
N1 C1 C6 C9 . 1.6(3)
C13 N1 C10 C11 . 0.6(3)
C1 N1 C10 C11 . 175.31(19)
C13 N1 C10 C14 . 174.22(19)
C1 N1 C10 C14 . -11.1(3)
N1 C10 C11 C12 . -2.0(3)
C14 C10 C11 C12 . -174.9(2)
N1 C10 C11 C16 . 174.7(2)
C14 C10 C11 C16 . 1.8(4)
C10 C11 C12 C18 . -174.2(2)
C16 C11 C12 C18 . 9.6(4)
C10 C11 C12 C13 . 2.4(2)
C16 C11 C12 C13 . -173.7(2)
C10 N1 C13 O5 . -178.0(2)
C1 N1 C13 O5 . 7.3(4)
C10 N1 C13 C12 . 0.9(2)
C1 N1 C13 C12 . -173.78(19)
C18 C12 C13 O5 . -6.4(4)
C11 C12 C13 O5 . 176.8(2)
C18 C12 C13 N1 . 174.8(2)
C11 C12 C13 N1 . -2.0(2)
C15 O2 C14 O1 . -3.6(4)
C15 O2 C14 C10 . 177.9(2)
C11 C10 C14 O1 . 93.9(3)
N1 C10 C14 O1 . -78.5(3)
C11 C10 C14 O2 . -87.5(3)
N1 C10 C14 O2 . 100.2(2)
C17 O4 C16 O3 . -0.1(4)
C17 O4 C16 C11 . 176.1(3)
C10 C11 C16 O3 . 6.6(4)
C12 C11 C16 O3 . -177.6(2)
C10 C11 C16 O4 . -169.5(2)
C12 C11 C16 O4 . 6.2(4)
C11 C12 C18 C18 3_565 176.3(3)
C13 C12 C18 C18 3_565 0.2(4)
