#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:14:32 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180174 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/70/7107099.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_7107099
loop_
_publ_author_name
'Rekha R. Avirah'
'Kuthanapillil Jyothish'
'Cherumuttathu H. Suresh'
Eringathodi
Suresh
'Danaboyina Ramaiah'
_publ_section_title
;
 Novel semisquaraine regioisomers: isolation, divergent chemical
 reactivity and photophysical properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              12822
_journal_paper_doi               10.1039/c1cc15261k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C21 H14 N O4'
_chemical_formula_weight         344.33
_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                85.292(2)
_cell_angle_beta                 75.940(2)
_cell_angle_gamma                62.358(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6579(12)
_cell_length_b                   9.1217(12)
_cell_length_c                   13.0877(18)
_cell_measurement_reflns_used    2918
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.52
_cell_volume                     887.6(2)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6776
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9787
_exptl_crystal_colour            'Wine Red'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.1044
_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)+(0.0740P)²+2.2670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2325
_reflns_number_gt                2899
_reflns_number_total             3416
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15261k.txt
_cod_data_source_block           2011parm
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7107099
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_calc_flag
_atom_site_refinement_flags
N1 N 0.8387(4) 0.7407(4) 0.5623(2) 0.0167(7) Uani 1 d .
O1 O 0.7314(3) 0.2335(3) 0.6339(2) 0.0200(6) Uani 1 d .
O2 O 0.8359(4) 0.0478(3) 0.8453(2) 0.0258(7) Uani 1 d .
O3 O 0.9922(4) 0.3111(3) 0.8742(2) 0.0280(7) Uani 1 d .
O4 O 0.5905(4) 1.1068(3) 0.2227(2) 0.0218(6) Uani 1 d .
C1 C 0.6646(5) 0.7979(5) 0.4306(3) 0.0176(8) Uani 1 d .
C2 C 0.5977(5) 0.8904(4) 0.3457(3) 0.0177(8) Uani 1 d .
H2 H 0.5238 0.8677 0.3156 0.021 Uiso 1 calc R
C3 C 0.6421(5) 1.0140(5) 0.3075(3) 0.0190(8) Uani 1 d .
C4 C 0.7427(5) 1.0538(5) 0.3578(3) 0.0198(8) Uani 1 d .
H4 H 0.7686 1.1404 0.3333 0.024 Uiso 1 calc R
C5 C 0.8045(5) 0.9690(4) 0.4423(3) 0.0159(8) Uani 1 d .
H5 H 0.8700 0.9991 0.4752 0.019 Uiso 1 calc R
C6 C 0.7685(5) 0.8357(4) 0.4792(3) 0.0171(8) Uani 1 d .
C7 C 0.8058(5) 0.6102(4) 0.5997(3) 0.0156(8) Uani 1 d .
C8 C 0.6940(5) 0.5765(4) 0.5500(3) 0.0181(8) Uani 1 d .
H8 H 0.6680 0.4898 0.5740 0.022 Uiso 1 calc R
C9 C 0.6257(5) 0.6647(5) 0.4704(3) 0.0190(8) Uani 1 d .
H9 H 0.5530 0.6392 0.4411 0.023 Uiso 1 calc R
C10 C 0.8735(5) 0.5166(5) 0.6827(3) 0.0193(8) Uani 1 d .
H10 H 0.9370 0.5505 0.7147 0.023 Uiso 1 calc R
C11 C 0.8555(5) 0.3767(4) 0.7227(3) 0.0172(8) Uani 1 d .
C12 C 0.7929(5) 0.2565(4) 0.7011(3) 0.0169(8) Uani 1 d .
C13 C 0.8440(5) 0.1680(4) 0.7999(3) 0.0179(8) Uani 1 d .
C14 C 0.9079(5) 0.2867(5) 0.8114(3) 0.0202(8) Uani 1 d .
C15 C 1.0201(6) 0.2015(5) 0.9648(3) 0.0266(9) Uani 1 d .
C16 C 0.8591 0.2690 1.0488 0.0222(14) Uani 0.62 d P
C16A C 0.9520 0.3126 1.0702 0.023(2) Uani 0.38 d P
C17 C 0.8232 0.4333 1.0941 0.036(2) Uani 0.61 d P
C17A C 0.7469 0.4255 1.0960 0.045(4) Uani 0.39 d P
C18 C 0.6614(10) 0.5132(8) 1.1862(6) 0.087(3) Uani 1 d .
C19 C 0.4806(5) 1.0728(5) 0.1720(3) 0.0233(9) Uani 1 d .
H19A H 0.3692 1.0915 0.2214 0.028 Uiso 1 calc R
H19B H 0.5423 0.9584 0.1463 0.028 Uiso 1 calc R
C20 C 0.4435(6) 1.1868(6) 0.0820(3) 0.0288(10) Uani 1 d .
H20A H 0.3933 1.2992 0.1073 0.043 Uiso 1 calc R
H20B H 0.3602 1.1747 0.0508 0.043 Uiso 1 calc R
H20C H 0.5533 1.1596 0.0300 0.043 Uiso 1 calc R
C21 C 0.9548(6) 0.7820(5) 0.6062(3) 0.0265(9) Uani 1 d .
H21A H 0.8877 0.8923 0.6368 0.040 Uiso 1 calc R
H21B H 1.0542 0.7755 0.5511 0.040 Uiso 1 calc R
H21C H 0.9987 0.7052 0.6594 0.040 Uiso 1 calc R
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 C6 122.0(3)
C7 N1 C21 120.4(3)
C6 N1 C21 117.6(3)
C14 O3 C15 115.2(3)
C3 O4 C19 117.2(3)
C6 C1 C2 120.6(3)
C6 C1 C9 118.1(3)
C2 C1 C9 121.3(3)
C3 C2 C1 119.7(3)
C3 C2 H2 120.1
C1 C2 H2 120.1
O4 C3 C2 124.5(3)
O4 C3 C4 116.0(3)
C2 C3 C4 119.4(3)
C5 C4 C3 121.7(3)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.7(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 N1 120.5(3)
C1 C6 C5 118.7(3)
N1 C6 C5 120.9(3)
N1 C7 C10 122.3(3)
N1 C7 C8 116.5(3)
C10 C7 C8 121.2(3)
C9 C8 C7 122.8(3)
C9 C8 H8 118.6
C7 C8 H8 118.6
C8 C9 C1 120.1(3)
C8 C9 H9 119.9
C1 C9 H9 119.9
C7 C10 C11 126.6(3)
C7 C10 H10 116.7
C11 C10 H10 116.7
C10 C11 C14 128.7(3)
C10 C11 C12 142.1(3)
C14 C11 C12 89.1(3)
O1 C12 C11 137.0(3)
O1 C12 C13 134.0(3)
C11 C12 C13 89.0(3)
O2 C13 C14 138.4(4)
O2 C13 C12 134.8(3)
C14 C13 C12 86.8(3)
O3 C14 C11 127.8(3)
O3 C14 C13 137.1(3)
C11 C14 C13 95.1(3)
C16 C15 O3 109.0(3)
O3 C15 C16A 108.8(3)
C15 C16 C17 112.18(16)
C17 C16A C15 127.52(15)
C17A C16A C15 112.36(16)
C16 C17 C18 117.1(3)
C18 C17A C16A 121.6(4)
O4 C19 C20 107.6(3)
O4 C19 H19A 110.2
C20 C19 H19A 110.2
O4 C19 H19B 110.2
C20 C19 H19B 110.2
H19A C19 H19B 108.5
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N1 C21 H21A 109.5
N1 C21 H21B 109.5
H21A C21 H21B 109.5
N1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.374(4)
N1 C6 1.408(5)
N1 C21 1.466(5)
O1 C12 1.209(4)
O2 C13 1.226(4)
O3 C14 1.315(5)
O3 C15 1.478(5)
O4 C3 1.372(4)
O4 C19 1.434(4)
C1 C6 1.391(5)
C1 C2 1.410(5)
C1 C9 1.433(5)
C2 C3 1.373(5)
C2 H2 0.9300
C3 C4 1.391(5)
C4 C5 1.368(5)
C4 H4 0.9300
C5 C6 1.411(5)
C5 H5 0.9300
C7 C10 1.395(5)
C7 C8 1.439(5)
C8 C9 1.342(5)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.401(5)
C10 H10 0.9300
C11 C14 1.408(5)
C11 C12 1.501(5)
C12 C13 1.515(5)
C13 C14 1.457(5)
C15 C16 1.449(4)
C15 C16A 1.599(4)
C16 C17 1.52210(19)
C16A C17A 1.5479(2)
C17 C18 1.524(6)
C19 C20 1.498(6)
C19 H19A 0.9700
C19 H19B 0.9700
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
