##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2006-06-02
_journal_date_accepted     2006-07-04
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o557
_journal_page_last     o560
_journal_paper_category     FO
_journal_coeditor_code     HJ3016
_publ_contact_author_name     'Jean Meinnel'
_publ_contact_author_address
;
UMR 6226 CNRS
Universite de Rennes 1 `Sciences Chimiques de Rennes'
Equipe `Materiaux Inorganiques, Chimie Douce et Reactivite'
Batiment 10B
Campus de Beaulieu
263 Avenue du General Leclerc
F-35042 Rennes
France
;
_publ_contact_author_email     jean.meinnel@univ-rennes1.fr
_publ_contact_author_fax     '00 33 2 23 23 57 80'
_publ_contact_author_phone     '00 33 2 23 23 68 40'
_publ_section_title
;
4-Dimethylamino-β-nitrostyrene and 4-dimethylamino-β-ethyl-β-nitrostyrene at
100 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Hamdellou, Lamine'
;
Laboratoire de Cristallographie
Département de Physique
Université Mentouri Constantine
25000 Constantine
Algeria
;
    'Hernandez, Olivier'
;
UMR 6226 CNRS
Université de Rennes 1 `Sciences Chimiques de Rennes'
Equipe `Matériaux Inorganiques, Chimie Douce et Réactivité'
Bâtiment 10B
Campus de Beaulieu
263 Avenue du Général Leclerc
F-35042 Rennes
France
;
    'Meinnel, Jean'
;
UMR 6226 CNRS
Université de Rennes 1 `Sciences Chimiques de Rennes'
Equipe `Matériaux Inorganiques, Chimie Douce et Réactivité'
Bâtiment 10B
Campus de Beaulieu
263 Avenue du Général Leclerc
F-35042 Rennes
France
;
data_I
_chemical_name_systematic
;
4-dimethyamino-β-nitrostyrene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H12 N2 O2'
_chemical_formula_sum     'C10 H12 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C10 H12 N2 O2'
_chemical_formula_weight     192.22
_chemical_melting_point     390
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     ?
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x+1/2,y+1/2,z'
    'x+1/2,-y+1/2,-z'
    'x,-y+1/2,z+1/2'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
    'x+1/2,y,-z+1/2'
_cell_length_a     10.1460(2)
_cell_length_b     7.3091(2)
_cell_length_c     25.1662(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1866.28(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5978
_cell_measurement_theta_min     2.579
_cell_measurement_theta_max     27.482
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'dark red'
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.16
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.368
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     816.02
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2002)'
_exptl_absorpt_correction_T_min     0.9751
_exptl_absorpt_correction_T_max     0.9846
_exptl_special_details
; ?
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     'horizontally mounted graphite crystal'
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_method     'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20691
_diffrn_reflns_av_R_equivalents     0.032
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     2.579
_diffrn_reflns_theta_max     27.482
_diffrn_reflns_theta_full     27.482
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     30
_diffrn_reflns_reduction_process     'Friedels'
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
; ?
;
_reflns_number_total     2137
_reflns_number_gt     1488
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0478
_refine_ls_R_factor_gt     0.0330
_refine_ls_wR_factor_all     0.0467
_refine_ls_wR_factor_ref     0.0371
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     1.1689
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     1488
_refine_ls_number_parameters     161
_refine_ls_number_restraints     60
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Prince (1982) modified Chebychev polynomial with five
parameters (Watkin, 1994): 1.34 1.99 1.39 0.636 0.244
;
_refine_ls_shift/su_max     0.000691
_refine_ls_shift/su_mean     ?
_refine_diff_density_max     0.22
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     0.0
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Watkin et al.,  2001)'
_computing_molecular_graphics     'CAMERON (Watkin et al.,  1996)'
_computing_publication_material     'CRYSTALS'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O11 0.30077(12) 0.52197(19) 0.33507(6) 0.0344 Uani 0.830(3) . .
    O O12 0.3140(7) 0.5475(9) 0.3566(3) 0.0208(9) Uiso 0.170(3) . .
    O O21 0.46427(19) 0.7099(3) 0.34689(6) 0.0335 Uani 0.830(3) . .
    O O22 0.4803(10) 0.7212(14) 0.3351(3) 0.0208(9) Uiso 0.170(3) . .
    N N1 0.39672(10) 0.73485(14) 0.67920(4) 0.0208 Uani 1.0000 . .
    N N21 0.37398(16) 0.6127(2) 0.36439(5) 0.0224 Uani 0.830(3) . .
    N N22 0.4071(8) 0.6536(13) 0.3677(3) 0.0208(9) Uiso 0.170(3) . .
    C C1 0.40288(10) 0.71801(15) 0.62546(5) 0.0176 Uani 1.0000 . .
    C C9 0.49764(12) 0.83659(19) 0.70776(5) 0.0251 Uani 1.0000 . .
    C C10 0.30262(13) 0.62660(19) 0.70947(5) 0.0290 Uani 1.0000 . .
    C C21 0.4998(3) 0.8158(4) 0.59644(7) 0.0170 Uani 0.830(3) . .
    C C22 0.4936(15) 0.796(3) 0.5895(4) 0.0208(9) Uiso 0.170(3) . .
    C C31 0.50576(15) 0.8036(2) 0.54137(6) 0.0169 Uani 0.830(3) . .
    C C32 0.4733(9) 0.7724(14) 0.5363(3) 0.0208(9) Uiso 0.170(3) . .
    C C41 0.41664(14) 0.6977(2) 0.51173(5) 0.0164 Uani 0.830(3) . .
    C C42 0.3747(8) 0.6570(12) 0.5184(2) 0.0208(9) Uiso 0.170(3) . .
    C C51 0.32284(15) 0.5975(2) 0.54076(6) 0.0181 Uani 0.830(3) . .
    C C52 0.2905(8) 0.5712(12) 0.5539(3) 0.0208(9) Uiso 0.170(3) . .
    C C61 0.31540(19) 0.6071(3) 0.59517(6) 0.0190 Uani 0.830(3) . .
    C C62 0.3010(12) 0.600(2) 0.6069(3) 0.0208(9) Uiso 0.170(3) . .
    C C71 0.42780(13) 0.69515(19) 0.45437(6) 0.0185 Uani 0.830(3) . .
    C C72 0.3606(7) 0.6261(9) 0.4620(2) 0.0208(9) Uiso 0.170(3) . .
    C C81 0.35170(14) 0.6022(2) 0.42047(5) 0.0209 Uani 0.830(3) . .
    C C82 0.4317(6) 0.7008(9) 0.4228(3) 0.0208(9) Uiso 0.170(3) . .
    H H91 0.4775 0.8344 0.7467 0.0336(13) Uiso 1.0000 . .
    H H92 0.4988 0.9661 0.6949 0.0336(13) Uiso 1.0000 . .
    H H93 0.5857 0.7793 0.7014 0.0336(13) Uiso 1.0000 . .
    H H101 0.3117 0.6558 0.7481 0.0336(13) Uiso 1.0000 . .
    H H102 0.3204 0.4935 0.7037 0.0336(13) Uiso 1.0000 . .
    H H103 0.2111 0.6562 0.6974 0.0336(13) Uiso 1.0000 . .
    H H211 0.5664 0.8932 0.6152 0.0336(13) Uiso 0.830(3) . .
    H H221 0.5676 0.8740 0.6030 0.0336(13) Uiso 0.170(3) . .
    H H311 0.5746 0.8736 0.5215 0.0336(13) Uiso 0.830(3) . .
    H H321 0.5337 0.8341 0.5104 0.0336(13) Uiso 0.170(3) . .
    H H511 0.2596 0.5161 0.5215 0.0336(13) Uiso 0.830(3) . .
    H H521 0.2223 0.4843 0.5403 0.0336(13) Uiso 0.170(3) . .
    H H611 0.2467 0.5356 0.6147 0.0336(13) Uiso 0.830(3) . .
    H H621 0.2381 0.5417 0.6324 0.0336(13) Uiso 0.170(3) . .
    H H710 0.5000 0.7717 0.4389 0.0336(13) Uiso 0.830(3) . .
    H H720 0.2860 0.5379 0.4577 0.0336(13) Uiso 0.170(3) . .
    H H810 0.2784 0.5243 0.4345 0.0341(13) Uiso 0.830(3) . .
    H H820 0.5017 0.7921 0.4316 0.0341(13) Uiso 0.170(3) . .
_geom_special_details     ?
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O11 N21 . . 1.2394(19) yes
    O12 N22 . . 1.254(7) no
    O21 N21 . . 1.240(2) yes
    O22 N22 . . 1.213(7) no
    N1 C1 . . 1.3595(15) yes
    N1 C9 . . 1.4554(15) yes
    N1 C10 . . 1.4554(15) yes
    N21 C81 . . 1.4313(19) yes
    N22 C82 . . 1.449(8) no
    C1 C21 . . 1.418(2) yes
    C1 C22 . . 1.413(8) no
    C1 C61 . . 1.423(2) yes
    C1 C62 . . 1.425(8) no
    C9 H91 . . 1.000 no
    C9 H92 . . 1.000 no
    C9 H93 . . 1.000 no
    C10 H101 . . 1.000 no
    C10 H102 . . 1.000 no
    C10 H103 . . 1.000 no
    C21 C31 . . 1.390(2) yes
    C21 H211 . . 1.000 no
    C22 C32 . . 1.367(9) no
    C22 H221 . . 1.000 no
    C31 C41 . . 1.4045(17) yes
    C31 H311 . . 1.000 no
    C32 C42 . . 1.383(8) no
    C32 H321 . . 1.000 no
    C41 C51 . . 1.4057(19) yes
    C41 C71 . . 1.448(2) yes
    C42 C52 . . 1.386(7) no
    C42 C72 . . 1.446(7) no
    C51 C61 . . 1.373(2) yes
    C51 H511 . . 1.000 no
    C52 C62 . . 1.353(8) no
    C52 H521 . . 1.000 no
    C61 H611 . . 1.000 no
    C62 H621 . . 1.000 no
    C71 C81 . . 1.336(2) yes
    C71 H710 . . 1.000 no
    C72 C82 . . 1.338(7) no
    C72 H720 . . 1.000 no
    C81 H810 . . 1.000 no
    C82 H820 . . 1.000 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C9 . . . 120.35(10) yes
    C1 N1 C10 . . . 120.11(10) yes
    C9 N1 C10 . . . 118.73(10) yes
    O21 N21 O11 . . . 122.53(15) yes
    O21 N21 C81 . . . 119.86(16) yes
    O11 N21 C81 . . . 117.61(16) yes
    O12 N22 O22 . . . 124.1(7) no
    O12 N22 C82 . . . 119.4(6) no
    O22 N22 C82 . . . 116.5(6) no
    N1 C1 C21 . . . 119.90(11) yes
    N1 C1 C61 . . . 123.75(11) yes
    C21 C1 C61 . . . 116.34(12) yes
    N1 C9 H91 . . . 109.359 no
    N1 C9 H92 . . . 109.436 no
    H91 C9 H92 . . . 109.476 no
    N1 C9 H93 . . . 109.603 no
    H91 C9 H93 . . . 109.477 no
    H92 C9 H93 . . . 109.476 no
    N1 C10 H101 . . . 109.432 no
    N1 C10 H102 . . . 109.509 no
    H101 C10 H102 . . . 109.476 no
    N1 C10 H103 . . . 109.459 no
    H101 C10 H103 . . . 109.475 no
    H102 C10 H103 . . . 109.476 no
    C1 C21 C31 . . . 120.75(13) yes
    C1 C21 H211 . . . 120.733 no
    C31 C21 H211 . . . 118.502 no
    C1 C22 C32 . . . 118.5(6) no
    C1 C22 H221 . . . 120.062 no
    C32 C22 H221 . . . 121.316 no
    C21 C31 C41 . . . 122.46(13) yes
    C21 C31 H311 . . . 119.781 no
    C41 C31 H311 . . . 117.752 no
    C22 C32 C42 . . . 120.4(5) no
    C22 C32 H321 . . . 119.118 no
    C42 C32 H321 . . . 120.437 no
    C31 C41 C51 . . . 116.55(12) yes
    C31 C41 C71 . . . 119.10(13) yes
    C51 C41 C71 . . . 124.35(13) yes
    C32 C42 C52 . . . 120.8(5) no
    C32 C42 C72 . . . 119.1(5) no
    C52 C42 C72 . . . 120.1(6) no
    C41 C51 C61 . . . 121.93(13) yes
    C41 C51 H511 . . . 119.521 no
    C61 C51 H511 . . . 118.547 no
    C42 C52 C62 . . . 121.1(5) no
    C42 C52 H521 . . . 119.452 no
    C62 C52 H521 . . . 119.447 no
    C1 C61 C51 . . . 121.91(13) yes
    C1 C61 H611 . . . 118.025 no
    C51 C61 H611 . . . 120.059 no
    C1 C62 H621 . . . 120.637 no
    C52 C62 H621 . . . 121.063 no
    C41 C71 C81 . . . 126.72(14) yes
    C41 C71 H710 . . . 115.910 no
    C81 C71 H710 . . . 117.371 no
    C42 C72 C82 . . . 127.4(5) no
    C42 C72 H720 . . . 106.341 no
    C82 C72 H720 . . . 126.283 no
    N21 C81 C71 . . . 120.71(14) yes
    N21 C81 H810 . . . 119.680 no
    C71 C81 H810 . . . 119.605 no
    N22 C82 C72 . . . 121.0(4) no
    N22 C82 H820 . . . 119.649 no
    C72 C82 H820 . . . 119.384 no
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C51 C41 C71 C81 . . . . 1.148 yes
    C31 C41 C71 C81 . . . . -179.887 yes
    C41 C71 C81 N21 . . . . 179.863 yes
    C71 C81 N21 O11 . . . . 179.363 yes
    C71 C81 N21 O21 . . . . -0.427 yes
    C21 C1 N1 C9 . . . . -6.750 yes
    C61 C1 N1 C10 . . . . 4.305 yes
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
    _geom_hbond_publ_flag
    C9 H91 O21 5_565 1.00 2.547 3.534(2) 169.19 yes
    C9 H93 O11 4_566 1.00 2.777 3.419(2) 122.24 yes
    C10 H101 O11 7_565 1.00 2.789 3.503(2) 128.75 yes
data_II
_chemical_name_systematic
;
4-dimethyamino-β-ethyl-β-nitrostyrene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 N2 O2'
_chemical_formula_sum     'C12 H16 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     'C12 H16 N2 O2'
_chemical_formula_iupac     'C12 H16 N2 O2'
_chemical_formula_weight     220.27
_chemical_melting_point     385
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     ?
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     5.96410(10)
_cell_length_b     8.44920(10)
_cell_length_c     23.1400(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1166.07(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5243
_cell_measurement_theta_min     2.910
_cell_measurement_theta_max     34.972
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.28
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.255
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     472.00
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2002)'
_exptl_absorpt_correction_T_min     0.9618
_exptl_absorpt_correction_T_max     0.9761
_exptl_special_details
; ?
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     'horizontally mounted graphite crystal'
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14807
_diffrn_reflns_av_R_equivalents     0.04
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     3.522
_diffrn_reflns_theta_max     35.028
_diffrn_reflns_theta_full     34.327
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     37
_diffrn_reflns_reduction_process     '?'
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
; ?
;
_reflns_number_total     5077
_reflns_number_gt     2017
_reflns_threshold_expression     I>3σ(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1289
_refine_ls_R_factor_gt     0.0377
_refine_ls_wR_factor_all     0.0768
_refine_ls_wR_factor_ref     0.0390
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     1.1373
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     2017
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Prince (1982) modified Chebychev polynomial with three
parameters (Watkin, 1994): 3.54 -1.10 3.21
;
_refine_ls_shift/su_max     0.000760
_refine_ls_shift/su_mean     ?
_refine_diff_density_max     0.28
_refine_diff_density_min     -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     0.0
_refine_ls_abs_structure_details     'Flack (1983), with 3060 Friedel pairs'
_refine_ls_abs_structure_Flack     0.7(14)
_refine_ls_abs_structure_Rogers     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C   ' 0.0033 0.0016 'International_Tables_Vol_IV_Table_2.2B'
    'H   ' 0.0000 0.0000 'International_Tables_Vol_IV_Table_2.2B'
    'N   ' 0.0061 0.0033 'International_Tables_Vol_IV_Table_2.2B'
    'O   ' 0.0106 0.0060 'International_Tables_Vol_IV_Table_2.2B'
_computing_data_collection     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'DIRAX (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Watkin et al.,  2001)'
_computing_molecular_graphics     'CAMERON (Watkin et al.,  1996)'
_computing_publication_material     'CRYSTALS'
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_occupancy
    O O1 0.3599(3) 0.32618(17) 0.74674(6) 0.0325 Uani 1.0000
    O O2 0.5309(3) 0.44741(16) 0.81591(6) 0.0338 Uani 1.0000
    N N1 0.3426(3) -0.15522(17) 1.09331(7) 0.0223 Uani 1.0000
    N N2 0.4204(3) 0.33512(18) 0.79755(7) 0.0217 Uani 1.0000
    C C1 0.3607(3) -0.06704(19) 1.04390(8) 0.0179 Uani 1.0000
    C C2 0.5465(3) 0.03552(19) 1.03515(8) 0.0196 Uani 1.0000
    C C3 0.5630(3) 0.1231(2) 0.98484(8) 0.0185 Uani 1.0000
    C C4 0.4058(3) 0.11429(19) 0.94029(7) 0.0168 Uani 1.0000
    C C5 0.2202(3) 0.01411(19) 0.94958(8) 0.0182 Uani 1.0000
    C C6 0.1980(3) -0.0745(2) 0.99990(7) 0.0194 Uani 1.0000
    C C7 0.4393(3) 0.21535(19) 0.89041(8) 0.0177 Uani 1.0000
    C C8 0.3523(3) 0.20757(19) 0.83686(8) 0.0194 Uani 1.0000
    C C9 0.4905(3) -0.1280(2) 1.14227(8) 0.0251 Uani 1.0000
    C C10 0.1492(3) -0.2571(2) 1.10196(9) 0.0277 Uani 1.0000
    C C11 0.1994(3) 0.08604(19) 0.81058(8) 0.0207 Uani 1.0000
    C C12 -0.0449(3) 0.1401(2) 0.80929(9) 0.0296 Uani 1.0000
    H H21 0.6648 0.0449 1.0656 0.021(2) Uiso 1.0000
    H H31 0.6940 0.1958 0.9802 0.021(2) Uiso 1.0000
    H H51 0.1012 0.0069 0.9192 0.021(2) Uiso 1.0000
    H H61 0.0643 -0.1445 1.0049 0.021(2) Uiso 1.0000
    H H71 0.5447 0.3057 0.8968 0.021(2) Uiso 1.0000
    H H91 0.4517 -0.2030 1.1742 0.0401(19) Uiso 1.0000
    H H92 0.4723 -0.0167 1.1562 0.0401(19) Uiso 1.0000
    H H93 0.6494 -0.1455 1.1301 0.0401(19) Uiso 1.0000
    H H101 0.1631 -0.3121 1.1401 0.0401(19) Uiso 1.0000
    H H102 0.0092 -0.1920 1.1015 0.0401(19) Uiso 1.0000
    H H103 0.1425 -0.3376 1.0703 0.0401(19) Uiso 1.0000
    H H111 0.2096 -0.0136 0.8338 0.0401(19) Uiso 1.0000
    H H112 0.2498 0.0648 0.7701 0.0401(19) Uiso 1.0000
    H H121 -0.1393 0.0554 0.7914 0.0401(19) Uiso 1.0000
    H H122 -0.0978 0.1609 0.8496 0.0401(19) Uiso 1.0000
    H H123 -0.0577 0.2392 0.7859 0.0401(19) Uiso 1.0000
_geom_special_details     ?
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N2 . . 1.232(2) yes
    O2 N2 . . 1.231(2) yes
    N1 C1 . . 1.369(2) yes
    N1 C9 . . 1.454(2) yes
    N1 C10 . . 1.453(2) yes
    N2 C8 . . 1.468(2) yes
    C1 C2 . . 1.421(2) yes
    C1 C6 . . 1.408(2) yes
    C2 C3 . . 1.383(2) yes
    C2 H21 . . 1.000 no
    C3 C4 . . 1.395(2) yes
    C3 H31 . . 1.000 no
    C4 C5 . . 1.410(2) yes
    C4 C7 . . 1.450(2) yes
    C5 C6 . . 1.391(3) yes
    C5 H51 . . 1.000 no
    C6 H61 . . 1.000 no
    C7 C8 . . 1.345(3) yes
    C7 H71 . . 1.000 no
    C8 C11 . . 1.502(2) yes
    C9 H91 . . 1.000 no
    C9 H92 . . 1.000 no
    C9 H93 . . 1.000 no
    C10 H101 . . 1.000 no
    C10 H102 . . 1.000 no
    C10 H103 . . 1.000 no
    C11 C12 . . 1.527(3) yes
    C11 H111 . . 1.000 no
    C11 H112 . . 1.000 no
    C12 H121 . . 1.000 no
    C12 H122 . . 1.000 no
    C12 H123 . . 1.000 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C9 . . . 121.12(15) yes
    C1 N1 C10 . . . 120.01(15) yes
    C9 N1 C10 . . . 117.89(15) yes
    O1 N2 O2 . . . 122.23(16) yes
    O1 N2 C8 . . . 117.74(15) yes
    O2 N2 C8 . . . 120.01(15) yes
    N1 C1 C2 . . . 120.82(15) yes
    N1 C1 C6 . . . 121.69(15) yes
    C2 C1 C6 . . . 117.50(15) yes
    C1 C2 C3 . . . 120.11(16) yes
    C1 C2 H21 . . . 119.900 no
    C3 C2 H21 . . . 119.988 no
    C2 C3 C4 . . . 123.06(15) yes
    C2 C3 H31 . . . 118.385 no
    C4 C3 H31 . . . 118.552 no
    C3 C4 C5 . . . 116.54(16) yes
    C3 C4 C7 . . . 117.66(15) yes
    C5 C4 C7 . . . 125.68(16) yes
    C4 C5 C6 . . . 121.70(16) yes
    C4 C5 H51 . . . 119.126 no
    C6 C5 H51 . . . 119.171 no
    C1 C6 C5 . . . 121.05(15) yes
    C1 C6 H61 . . . 119.551 no
    C5 C6 H61 . . . 119.396 no
    C4 C7 C8 . . . 130.66(16) yes
    C4 C7 H71 . . . 114.692 no
    C8 C7 H71 . . . 114.643 no
    N2 C8 C7 . . . 115.37(16) yes
    N2 C8 C11 . . . 114.77(16) yes
    C7 C8 C11 . . . 129.85(16) yes
    N1 C9 H91 . . . 109.552 no
    N1 C9 H92 . . . 109.511 no
    H91 C9 H92 . . . 109.476 no
    N1 C9 H93 . . . 109.336 no
    H91 C9 H93 . . . 109.476 no
    H92 C9 H93 . . . 109.476 no
    N1 C10 H101 . . . 109.339 no
    N1 C10 H102 . . . 109.584 no
    H101 C10 H102 . . . 109.476 no
    N1 C10 H103 . . . 109.476 no
    H101 C10 H103 . . . 109.476 no
    H102 C10 H103 . . . 109.476 no
    C8 C11 C12 . . . 112.52(14) yes
    C8 C11 H111 . . . 108.722 no
    C12 C11 H111 . . . 108.685 no
    C8 C11 H112 . . . 108.623 no
    C12 C11 H112 . . . 108.790 no
    H111 C11 H112 . . . 109.466 no
    C11 C12 H121 . . . 109.328 no
    C11 C12 H122 . . . 109.590 no
    H121 C12 H122 . . . 109.476 no
    C11 C12 H123 . . . 109.482 no
    H121 C12 H123 . . . 109.475 no
    H122 C12 H123 . . . 109.476 no
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 C4 C7 C8 . . . . -21.9(3) yes
    C3 C4 C7 C8 . . . . 162.26(19) yes
    C4 C7 C8 N2 . . . . 178.23(17) yes
    C7 C8 N2 O1 . . . . 174.21(17) yes
    C7 C8 N2 O2 . . . . -7.0(3) yes
    C2 C1 N1 C9 . . . . 10.4(3) yes
    C6 C1 N1 C10 . . . . -1.4(3) yes
    C4 C7 C8 C11 . . . . -3.3(3) yes
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
    _geom_hbond_publ_flag
    C10 H101 O1 4_555 1.00 2.472 3.401(2) 153.78 yes
    C12 H121 O1 3_546 1.00 2.502 3.499(2) 174.75 yes
    C9 H92 O2 2_457 1.00 2.773 3.283(2) 112.12 yes
    C10 H102 O2 2_457 1.00 2.817 3.310(2) 111.01 yes
    C11 H112 O2 3_646 1.00 2.580 3.539(2) 160.74 yes
