#------------------------------------------------------------------------------
#$Date: 2017-03-04 10:08:31 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193278 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032297.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_4032297
loop_
_publ_author_name
'Zhu, Qiuhua'
'Ye, Ziwei'
'Yang, Weijie'
'Cai, Xiaotie'
'Tang, Ben Zhong'
_publ_section_title
;
 One-Pot Synthesis and Structure-Property Relationship of Aminomaleimides:
 Fluorescence Efficiencies in Monomers and Aggregates Easily Tuned by
 Switch of Aryl and Alkyl.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1096
_journal_page_last               1104
_journal_paper_doi               10.1021/acs.joc.6b02706
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C14 H22 N2 O2'
_chemical_formula_weight         250.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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
_cell_angle_alpha                110.06(3)
_cell_angle_beta                 102.97(3)
_cell_angle_gamma                92.87(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1414(12)
_cell_length_b                   10.463(2)
_cell_length_c                   12.483(3)
_cell_measurement_temperature    293(2)
_cell_volume                     727.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7047
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0822
_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)+(0.1633P)²+0.0074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2384
_refine_ls_wR_factor_ref         0.3025
_reflns_number_gt                1471
_reflns_number_total             3292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02706_si_003.cif
_cod_data_source_block           1
_cod_original_cell_volume        727.2(3)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               4032297
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
N1 N 0.3166(4) 0.6772(3) 0.5841(2) 0.0742(8) Uani 1 1 d .
C10 C -0.0067(5) 0.6962(3) 0.4372(3) 0.0752(9) Uani 1 1 d .
N2 N -0.0488(4) 0.7820(3) 0.3775(2) 0.0820(9) Uani 1 1 d .
C7 C 0.2295(5) 0.7431(3) 0.5146(3) 0.0642(8) Uani 1 1 d .
O2 O -0.1360(4) 0.6010(2) 0.4308(2) 0.1042(10) Uani 1 1 d .
C4 C 0.5410(5) 0.7226(3) 0.6649(3) 0.0786(10) Uani 1 1 d .
H4 H 0.6384 0.7588 0.6266 0.094 Uiso 1 1 calc R
O1 O 0.1431(5) 0.9735(3) 0.3734(3) 0.1196(11) Uani 1 1 d .
C9 C 0.1431(6) 0.8824(3) 0.4119(3) 0.0843(11) Uani 1 1 d .
C8 C 0.3130(5) 0.8536(3) 0.4968(3) 0.0746(9) Uani 1 1 d .
H8 H 0.4567 0.9028 0.5334 0.090 Uiso 1 1 calc R
C3 C 0.6415(7) 0.6062(4) 0.6922(4) 0.1013(12) Uani 1 1 d .
H3A H 0.6497 0.5347 0.6197 0.122 Uiso 1 1 calc R
H3B H 0.5466 0.5673 0.7290 0.122 Uiso 1 1 calc R
C11 C -0.2708(6) 0.7879(4) 0.3059(4) 0.0976(12) Uani 1 1 d .
H11A H -0.3882 0.7506 0.3318 0.117 Uiso 1 1 calc R
H11B H -0.2884 0.8830 0.3174 0.117 Uiso 1 1 calc R
C5 C 0.5345(8) 0.8354(4) 0.7761(4) 0.1221(18) Uani 1 1 d .
H5A H 0.4378 0.8019 0.8153 0.147 Uiso 1 1 calc R
H5B H 0.4712 0.9106 0.7573 0.147 Uiso 1 1 calc R
C2 C 0.8774(7) 0.6578(5) 0.7750(5) 0.1174(15) Uani 1 1 d .
H2A H 0.9378 0.5827 0.7952 0.141 Uiso 1 1 calc R
H2B H 0.9751 0.6878 0.7345 0.141 Uiso 1 1 calc R
C1 C 0.8781(8) 0.7727(4) 0.8846(4) 0.1236(17) Uani 1 1 d .
H1A H 1.0325 0.8071 0.9312 0.148 Uiso 1 1 calc R
H1B H 0.7981 0.7396 0.9308 0.148 Uiso 1 1 calc R
C6 C 0.7690(10) 0.8869(5) 0.8583(5) 0.169(3) Uani 1 1 d .
H6A H 0.8613 0.9287 0.8221 0.203 Uiso 1 1 calc R
H6B H 0.7595 0.9567 0.9314 0.203 Uiso 1 1 calc R
C14 C -0.7079(9) 0.6370(7) 0.1086(6) 0.162(2) Uani 1 1 d .
H14A H -0.6777 0.5438 0.0805 0.243 Uiso 1 1 calc R
H14B H -0.8464 0.6455 0.0592 0.243 Uiso 1 1 calc R
H14C H -0.7208 0.6618 0.1882 0.243 Uiso 1 1 calc R
C12 C -0.2966(9) 0.7107(6) 0.1808(4) 0.1391(19) Uani 1 1 d .
H12A H -0.2869 0.6146 0.1684 0.167 Uiso 1 1 calc R
H12B H -0.1755 0.7451 0.1553 0.167 Uiso 1 1 calc R
C13 C -0.5306(10) 0.7246(7) 0.1056(5) 0.157(2) Uani 1 1 d .
H13A H -0.5599 0.8188 0.1358 0.188 Uiso 1 1 calc R
H13B H -0.5240 0.7029 0.0244 0.188 Uiso 1 1 calc R
H1 H 0.257(7) 0.605(4) 0.588(3) 0.103(12) Uiso 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'
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
C7 N1 C4 122.2(2)
O2 C10 N2 126.6(3)
O2 C10 C7 126.6(3)
N2 C10 C7 106.8(2)
C10 N2 C9 109.4(2)
C10 N2 C11 125.3(3)
C9 N2 C11 124.3(3)
N1 C7 C8 132.2(3)
N1 C7 C10 120.1(2)
C8 C7 C10 107.7(3)
N1 C4 C5 110.8(3)
N1 C4 C3 111.6(3)
C5 C4 C3 110.3(3)
O1 C9 N2 121.6(3)
O1 C9 C8 130.8(3)
N2 C9 C8 107.5(2)
C7 C8 C9 108.5(3)
C4 C3 C2 109.8(3)
C12 C11 N2 111.4(4)
C4 C5 C6 110.9(4)
C1 C2 C3 112.4(4)
C2 C1 C6 111.3(4)
C1 C6 C5 111.3(4)
C11 C12 C13 110.4(5)
C14 C13 C12 111.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.324(4)
N1 C4 1.457(4)
C10 O2 1.212(3)
C10 N2 1.350(4)
C10 C7 1.501(4)
N2 C9 1.420(4)
N2 C11 1.470(4)
C7 C8 1.348(4)
C4 C5 1.493(6)
C4 C3 1.499(5)
O1 C9 1.206(4)
C9 C8 1.434(4)
C3 C2 1.525(5)
C11 C12 1.458(6)
C5 C6 1.516(6)
C2 C1 1.478(6)
C1 C6 1.496(6)
C14 C13 1.403(8)
C12 C13 1.574(6)
