#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/62/2206254.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_2206254
loop_
_publ_author_name
'Yu-Cheng Wang'
'Xiang-Shan Wang'
'Zhao-Sen Zeng'
'Da-Qing Shi'
_publ_section_title
;Diethyl
 2,8-diamino-4,10-bis(3-nitrophenyl)naphtho[1,2-b;6,5-b']dipyran-3,9-dicarboxylate
 dimethylformamide disolvate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2027
_journal_page_last               o2029
_journal_paper_doi               10.1107/S1600536805017113
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C34 H28 N4 O10 , 2C3 H7 N O'
_chemical_formula_moiety         'C34 H28 N4 O10 , 2C3 H7 N O'
_chemical_formula_sum            'C40 H42 N6 O12'
_chemical_formula_weight         798.80
_chemical_melting_point          560.0(10)
_chemical_name_systematic
;
Diethyl 2,8-diamino-4,10-bis(3-nitrophenyl)naphtha[1,2-b;6,5-b']dipyran-
3,9-dicarboxylate dimethylformamide disolvate
;
_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
_cell_angle_alpha                99.292(3)
_cell_angle_beta                 96.912(3)
_cell_angle_gamma                97.103(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3550(10)
_cell_length_b                   9.7500(10)
_cell_length_c                   12.202(2)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    289(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      3.26
_cell_volume                     963.4(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      289(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0325
_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       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5054
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        2.26
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0707
_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)+(0.16P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2198
_refine_ls_wR_factor_ref         0.2415
_reflns_number_gt                2241
_reflns_number_total             3340
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6529.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '559-561' was changed to '560.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '559-561' was changed to '560.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206254
_cod_database_fobs_code          2206254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2720(2) 0.33760(19) 0.54942(16) 0.0541(6) Uani d . 1 O
O2 0.7598(2) 0.5894(2) 0.75623(17) 0.0615(6) Uani d . 1 O
O3 0.7614(2) 0.3615(2) 0.68959(18) 0.0670(6) Uani d . 1 O
O4 0.6779(4) 0.9562(4) 1.0344(3) 0.1178(11) Uani d . 1 O
O5 0.5458(5) 0.9030(5) 1.1671(3) 0.1482(15) Uani d . 1 O
N1 0.4824(3) 0.2222(3) 0.5621(2) 0.0673(8) Uani d D 1 N
N2 0.5741(5) 0.8809(5) 1.0713(3) 0.1006(11) Uani d . 1 N
C1 0.4318(3) 0.3454(3) 0.5917(2) 0.0506(7) Uani d . 1 C
C2 0.5197(3) 0.4645(3) 0.6550(2) 0.0500(7) Uani d . 1 C
C3 0.4431(3) 0.5960(3) 0.6861(2) 0.0481(7) Uani d . 1 C
H3 0.5147 0.6768 0.6720 0.058 Uiso calc R 1 H
C4 0.2783(3) 0.5847(3) 0.6150(2) 0.0458(7) Uani d . 1 C
C5 0.2013(3) 0.4587(3) 0.5568(2) 0.0443(6) Uani d . 1 C
C6 0.0395(3) 0.4396(3) 0.4986(2) 0.0442(7) Uani d . 1 C
C7 -0.0439(3) 0.3078(3) 0.4415(2) 0.0503(7) Uani d . 1 C
H7 0.0065 0.2279 0.4419 0.060 Uiso calc R 1 H
C8 -0.1972(3) 0.2969(3) 0.3861(2) 0.0501(7) Uani d . 1 C
H8 -0.2499 0.2095 0.3480 0.060 Uiso calc R 1 H
C9 0.6884(3) 0.4624(3) 0.6987(2) 0.0537(7) Uani d . 1 C
C10 0.9266(3) 0.5975(4) 0.8062(3) 0.0644(9) Uani d . 1 C
H10A 0.9930 0.5657 0.7499 0.077 Uiso calc R 1 H
H10B 0.9342 0.5400 0.8639 0.077 Uiso calc R 1 H
C11 0.9802(5) 0.7468(5) 0.8548(4) 0.1124(15) Uani d . 1 C
H11A 0.9642 0.8026 0.7975 0.135 Uiso calc R 1 H
H11B 1.0937 0.7603 0.8851 0.135 Uiso calc R 1 H
H11C 0.9177 0.7748 0.9135 0.135 Uiso calc R 1 H
C12 0.4220(3) 0.6202(3) 0.8102(2) 0.0495(7) Uani d . 1 C
C13 0.3248(3) 0.5227(3) 0.8526(3) 0.0585(8) Uani d . 1 C
H13 0.2717 0.4416 0.8047 0.070 Uiso calc R 1 H
C14 0.3042(4) 0.5424(5) 0.9638(3) 0.0761(10) Uani d . 1 C
H14 0.2369 0.4755 0.9900 0.091 Uiso calc R 1 H
C15 0.3828(5) 0.6606(5) 1.0361(3) 0.0812(11) Uani d . 1 C
H15 0.3690 0.6754 1.1114 0.097 Uiso calc R 1 H
C16 0.4813(4) 0.7552(4) 0.9948(3) 0.0700(9) Uani d . 1 C
C17 0.5021(3) 0.7387(3) 0.8840(3) 0.0615(8) Uani d . 1 C
H17 0.5694 0.8064 0.8585 0.074 Uiso calc R 1 H
O6 0.2412(5) 0.0044(4) 0.4304(4) 0.1433(16) Uani d . 1 O
N3 0.0765(4) -0.0776(3) 0.2691(3) 0.0800(9) Uani d . 1 N
C18 0.2132(7) -0.0243(6) 0.3366(6) 0.1238(18) Uani d . 1 C
H18 0.3028 -0.0074 0.2996 0.149 Uiso calc R 1 H
C19 -0.0632(7) -0.1170(7) 0.3137(5) 0.145(2) Uani d . 1 C
H19A -0.0836 -0.2175 0.3049 0.174 Uiso calc R 1 H
H19B -0.1540 -0.0842 0.2751 0.174 Uiso calc R 1 H
H19C -0.0489 -0.0765 0.3920 0.174 Uiso calc R 1 H
C20 0.0655(8) -0.1314(7) 0.1510(5) 0.155(2) Uani d . 1 C
H20A 0.1631 -0.0960 0.1243 0.186 Uiso calc R 1 H
H20B -0.0267 -0.1019 0.1112 0.186 Uiso calc R 1 H
H20C 0.0527 -0.2322 0.1388 0.186 Uiso calc R 1 H
H1A 0.5800(18) 0.211(3) 0.586(2) 0.066(9) Uiso d D 1 H
H1B 0.420(4) 0.153(3) 0.519(2) 0.082(12) Uiso d D 1 H
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
_geom_angle_publ_flag
C1 O1 C5 . . 119.3(2) yes
C9 O2 C10 . . 115.8(2) ?
C1 N1 H1A . . 120(2) ?
C1 N1 H1B . . 122(3) ?
H1A N1 H1B . . 118(3) ?
O5 N2 O4 . . 123.7(4) ?
O5 N2 C16 . . 117.9(4) ?
O4 N2 C16 . . 118.4(4) ?
N1 C1 C2 . . 127.6(3) ?
N1 C1 O1 . . 109.9(2) ?
C2 C1 O1 . . 122.5(2) yes
C1 C2 C9 . . 118.7(3) ?
C1 C2 C3 . . 121.7(2) yes
C9 C2 C3 . . 119.5(3) ?
C2 C3 C4 . . 110.4(2) yes
C2 C3 C12 . . 111.0(2) ?
C4 C3 C12 . . 109.29(19) ?
C2 C3 H3 . . 108.7 ?
C4 C3 H3 . . 108.7 ?
C12 C3 H3 . . 108.7 ?
C5 C4 C8 . 2_566 118.5(2) ?
C5 C4 C3 . . 120.7(2) yes
C8 C4 C3 2_566 . 120.7(2) ?
C4 C5 O1 . . 123.1(2) yes
C4 C5 C6 . . 122.9(2) ?
O1 C5 C6 . . 114.0(2) ?
C7 C6 C6 . 2_566 119.8(3) ?
C7 C6 C5 . . 123.3(2) ?
C6 C6 C5 2_566 . 116.9(3) ?
C8 C7 C6 . . 120.4(2) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C4 . 2_566 121.4(3) ?
C7 C8 H8 . . 119.3 ?
C4 C8 H8 2_566 . 119.3 ?
O3 C9 O2 . . 121.7(2) ?
O3 C9 C2 . . 126.8(3) ?
O2 C9 C2 . . 111.4(2) ?
O2 C10 C11 . . 105.4(3) ?
O2 C10 H10A . . 110.7 ?
C11 C10 H10A . . 110.7 ?
O2 C10 H10B . . 110.7 ?
C11 C10 H10B . . 110.7 ?
H10A C10 H10B . . 108.8 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C17 . . 117.9(3) ?
C13 C12 C3 . . 120.7(3) ?
C17 C12 C3 . . 121.4(3) ?
C14 C13 C12 . . 121.7(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C15 C14 C13 . . 120.1(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 118.2(3) ?
C16 C15 H15 . . 120.9 ?
C14 C15 H15 . . 120.9 ?
C15 C16 C17 . . 122.7(3) ?
C15 C16 N2 . . 119.9(3) ?
C17 C16 N2 . . 117.5(3) ?
C16 C17 C12 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C12 C17 H17 . . 120.3 ?
C18 N3 C19 . . 119.8(5) ?
C18 N3 C20 . . 124.9(5) ?
C19 N3 C20 . . 113.5(5) ?
O6 C18 N3 . . 131.8(7) ?
O6 C18 H18 . . 114.1 ?
N3 C18 H18 . . 114.1 ?
N3 C19 H19A . . 109.5 ?
N3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
N3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N3 C20 H20A . . 109.5 ?
N3 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
N3 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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
O1 C1 . 1.360(3) yes
O1 C5 . 1.379(3) yes
O2 C9 . 1.348(4) ?
O2 C10 . 1.440(3) ?
O3 C9 . 1.218(4) ?
O4 N2 . 1.240(5) ?
O5 N2 . 1.212(4) ?
N1 C1 . 1.332(4) yes
N1 H1A . 0.859(10) ?
N1 H1B . 0.859(10) ?
N2 C16 . 1.481(5) ?
C1 C2 . 1.359(4) yes
C2 C9 . 1.450(4) ?
C2 C3 . 1.518(4) yes
C3 C4 . 1.518(3) yes
C3 C12 . 1.529(4) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.357(4) yes
C4 C8 2_566 1.410(4) ?
C5 C6 . 1.425(4) ?
C6 C7 . 1.412(4) ?
C6 C6 2_566 1.417(5) yes
C7 C8 . 1.358(4) ?
C7 H7 . 0.9300 ?
C8 C4 2_566 1.410(4) ?
C8 H8 . 0.9300 ?
C10 C11 . 1.472(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.378(4) ?
C12 C17 . 1.386(4) ?
C13 C14 . 1.374(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.372(6) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.358(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.371(4) ?
C17 H17 . 0.9300 ?
O6 C18 . 1.122(6) ?
N3 C18 . 1.320(6) ?
N3 C19 . 1.384(5) ?
N3 C20 . 1.439(6) ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O3 0.859(10) 2.11(3) 2.713(3) 127(3)
N1 H1B O6 0.859(10) 2.015(13) 2.866(5) 170(4)
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_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C1 N1 . . -171.0(2) ?
C5 O1 C1 C2 . . 9.4(4) yes
N1 C1 C2 C9 . . -0.9(5) ?
O1 C1 C2 C9 . . 178.7(2) ?
N1 C1 C2 C3 . . -177.4(3) ?
O1 C1 C2 C3 . . 2.1(4) yes
C1 C2 C3 C4 . . -13.9(4) yes
C9 C2 C3 C4 . . 169.6(2) ?
C1 C2 C3 C12 . . 107.5(3) ?
C9 C2 C3 C12 . . -69.1(3) ?
C2 C3 C4 C5 . . 15.8(3) yes
C12 C3 C4 C5 . . -106.6(3) ?
C2 C3 C4 C8 . 2_566 -168.4(2) ?
C12 C3 C4 C8 . 2_566 69.2(3) ?
C8 C4 C5 O1 2_566 . 177.8(2) ?
C3 C4 C5 O1 . . -6.3(4) yes
C8 C4 C5 C6 2_566 . -2.8(4) ?
C3 C4 C5 C6 . . 173.1(2) ?
C1 O1 C5 C4 . . -7.2(4) yes
C1 O1 C5 C6 . . 173.2(2) ?
C4 C5 C6 C7 . . -177.4(2) ?
O1 C5 C6 C7 . . 2.2(4) ?
C4 C5 C6 C6 . 2_566 1.3(4) ?
O1 C5 C6 C6 . 2_566 -179.2(3) ?
C6 C6 C7 C8 2_566 . 2.4(4) ?
C5 C6 C7 C8 . . -179.0(2) ?
C6 C7 C8 C4 . 2_566 -0.9(4) ?
C10 O2 C9 O3 . . -0.3(4) ?
C10 O2 C9 C2 . . 178.2(2) ?
C1 C2 C9 O3 . . -3.8(4) ?
C3 C2 C9 O3 . . 172.8(3) ?
C1 C2 C9 O2 . . 177.9(2) ?
C3 C2 C9 O2 . . -5.5(3) ?
C9 O2 C10 C11 . . 175.3(3) ?
C2 C3 C12 C13 . . -61.3(3) ?
C4 C3 C12 C13 . . 60.7(3) ?
C2 C3 C12 C17 . . 117.3(3) ?
C4 C3 C12 C17 . . -120.7(3) ?
C17 C12 C13 C14 . . 1.3(4) ?
C3 C12 C13 C14 . . 180.0(2) ?
C12 C13 C14 C15 . . -0.8(5) ?
C13 C14 C15 C16 . . -0.6(5) ?
C14 C15 C16 C17 . . 1.4(5) ?
C14 C15 C16 N2 . . -177.2(3) ?
O5 N2 C16 C15 . . -7.6(5) ?
O4 N2 C16 C15 . . 171.2(3) ?
O5 N2 C16 C17 . . 173.6(3) ?
O4 N2 C16 C17 . . -7.5(5) ?
C15 C16 C17 C12 . . -0.9(4) ?
N2 C16 C17 C12 . . 177.8(3) ?
C13 C12 C17 C16 . . -0.5(4) ?
C3 C12 C17 C16 . . -179.2(2) ?
C19 N3 C18 O6 . . -4.6(8) ?
C20 N3 C18 O6 . . -168.6(6) ?
