#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010326.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_2010326
loop_
_publ_author_name
'Millini, Roberto'
'Piero, Gasto Del'
'Allegrini, Pietro'
'Nodari, Nereo'
_publ_section_title
;Chemical degradation of spiroindolinonaphthoxazines:
 8,13,13-trimethyl-7a,8-dihydronaphtho[2,1-b]quinolino[3,2-e][1,4]oxazine,
 C₂₂H₂₀N₂O
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2096
_journal_page_last               2098
_journal_paper_doi               10.1107/S0108270194004968
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.41
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            8
_cell_length_a                   29.464(7)
_cell_length_b                   13.861(4)
_cell_length_c                   8.515(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      14
_cell_volume                     3477.5(15)
_diffrn_measurement_device       'Siemens AED'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3776
_diffrn_reflns_theta_max         70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.5726
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.2545
_exptl_crystal_description       prism
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.54
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2038
_refine_ls_R_factor_obs          0.0564
_refine_ls_shift/esd_max         0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0453
_reflns_number_observed          2038
_reflns_number_total             3312
_reflns_observed_criterion       I>2.5(I)
_cod_data_source_file            na1085.cif
_cod_data_source_block           na1085_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C22 H20 N2 O1'
_cod_database_code               2010326
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2+y,-z
x,1/2-y,1/2+z
1/2-x,y,1/2+z
-x,-y,-z
1/2-x,1/2-y,z
-x,1/2+y,1/2-z
1/2+x,-y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) .07100(10) .0464(2) .3216(4) 0.0490(10)
C(2) .09280(10) .0824(3) .1900(5) 0.0440(10)
C(3) .0687(2) .1456(3) .0905(6) 0.0500(10)
C(4) .0901(2) .1838(3) -.0385(6) 0.0490(10)
C(5) .1361(2) .1589(3) -.0713(5) 0.0450(10)
C(6) .1585(2) .1967(3) -.2060(6) 0.054(2)
C(7) .2022(2) .1720(4) -.2358(6) 0.062(2)
C(8) .2258(2) .1083(4) -.1379(6) 0.060(2)
C(9) .2053(2) .0689(4) -.0099(6) 0.051(2)
C(10) .15960(10) .0938(3) .0241(5) 0.0420(10)
C(11) .13690(10) .0556(3) .1602(5) 0.0410(10)
N(12) .15810(10) -.0184(3) .2483(5) 0.0460(10)
C(13) .14090(10) -.0382(2) .3829(5) 0.044(2)
C(14) .1570(2) -.1214(3) .4811(6) 0.048(2)
C(15) .1139(2) -.1762(3) .5264(6) 0.048(2)
C(16) .1113(2) -.2770(4) .5289(7) 0.060(2)
C(17) .0724(2) -.3229(4) .5812(7) 0.071(2)
C(18) .0364(2) -.2699(5) .6299(8) 0.079(2)
C(19) .0374(2) -.1699(4) .6250(7) 0.064(2)
C(20) .0759(2) -.1237(3) .5731(6) 0.051(2)
N(21) .07890(10) -.0216(3) .5717(5) 0.0540(10)
C(22) .1027(2) .0237(3) .4485(5) 0.0450(10)
C(23) .1796(2) -.0801(4) .6291(6) 0.062(2)
C(24) .1917(2) -.1819(4) .3930(7) 0.066(2)
C(25) .0461(2) .0378(4) .6558(6) 0.064(2)
H3 .0278 .1588 .1036 ?
H4 .0694 .2354 -.1031 ?
H6 .1401 .2577 -.2850 ?
H7 .2209 .1965 -.3393 ?
H8 .2593 .0847 -.1653 ?
H9 .2244 .0129 .0656 ?
H16 .1385 -.3120 .4780 ?
H17 .0766 -.4080 .5659 ?
H18 .0068 -.3097 .6533 ?
H19 .0059 -.1299 .6561 ?
H22 .1179 .0942 .4854 ?
H23a .2070 -.0356 .6032 ?
H23b .1918 -.1333 .7031 ?
H23c .1543 -.0380 .6910 ?
H24a .2067 -.2288 .4793 ?
H24b .1762 -.2102 .2864 ?
H24c .2179 -.1409 .3520 ?
H25a .0067 .0261 .6313 ?
H25b .0452 .0146 .7822 ?
H25c .0660 .1090 .6484 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) O(1) C(22) 112.3(3) yes
O(1) C(2) C(3) 118.5(4) yes
C(2) C(3) C(4) 119.3(5) yes
C(4) C(5) C(10) 120.9(4) yes
C(6) C(5) C(10) 118.5(4) yes
C(6) C(7) C(8) 121.3(5) yes
C(8) C(9) C(10) 119.1(5) yes
C(9) C(10) C(11) 121.0(3) yes
C(2) C(11) C(10) 119.2(3) yes
C(2) C(11) N(12) 121.0(3) yes
N(12) C(13) C(22) 120.0(4) yes
C(14) C(13) C(22) 117.5(4) yes
C(13) C(14) C(23) 107.9(4) yes
C(23) C(14) C(24) 108.6(5) yes
C(15) C(14) C(23) 109.8(4) yes
C(14) C(15) C(16) 123.0(5) yes
C(15) C(16) C(17) 120.6(5) yes
C(17) C(18) C(19) 121.1(6) yes
C(15) C(20) C(19) 120.8(4) yes
C(15) C(20) N(21) 118.0(5) yes
C(20) N(21) C(22) 118.8(4) yes
C(13) C(22) N(21) 113.0(4) yes
O(1) C(22) C(13) 108.8(3) yes
O(1) C(2) C(11) 119.4(4) yes
C(3) C(2) C(11) 122.2(4) yes
C(3) C(4) C(5) 120.0(4) yes
C(4) C(5) C(6) 120.6(5) yes
C(5) C(6) C(7) 119.9(5) yes
C(7) C(8) C(9) 120.7(5) yes
C(5) C(10) C(9) 120.6(4) yes
C(5) C(10) C(11) 118.4(3) yes
C(10) C(11) N(12) 119.2(3) yes
C(11) N(12) C(13) 117.0(3) yes
N(12) C(13) C(14) 122.5(4) yes
C(13) C(14) C(24) 111.2(4) yes
C(13) C(14) C(15) 105.1(4) yes
C(15) C(14) C(24) 114.1(4) yes
C(14) C(15) C(20) 118.7(4) yes
C(16) C(15) C(20) 118.2(5) yes
C(16) C(17) C(18) 119.8(6) yes
C(18) C(19) C(20) 119.5(5) yes
C(19) C(20) N(21) 121.3(5) yes
C(20) N(21) C(25) 121.2(4) yes
C(22) N(21) C(25) 116.4(4) yes
O(1) C(22) N(21) 109.2(4) yes
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
O(1) C(2) . . 1.385(5) yes
C(2) C(3) . . 1.411(6) yes
C(3) C(4) . . 1.373(7) yes
C(5) C(6) . . 1.423(7) yes
C(6) C(7) . . 1.356(8) yes
C(8) C(9) . . 1.361(8) yes
C(10) C(11) . . 1.439(6) yes
N(12) C(13) . . 1.283(6) yes
C(13) C(22) . . 1.522(6) yes
C(14) C(23) . . 1.536(7) yes
C(15) C(16) . . 1.399(7) yes
C(16) C(17) . . 1.385(8) yes
C(18) C(19) . . 1.387(9) yes
C(20) N(21) . . 1.418(6) yes
N(21) C(25) . . 1.458(7) yes
O(1) C(22) . . 1.463(6) yes
C(2) C(11) . . 1.375(4) yes
C(4) C(5) . . 1.426(8) yes
C(5) C(10) . . 1.398(6) yes
C(7) C(8) . . 1.399(8) yes
C(9) C(10) . . 1.420(7) yes
C(11) N(12) . . 1.416(6) yes
C(13) C(14) . . 1.501(6) yes
C(14) C(15) . . 1.529(8) yes
C(14) C(24) . . 1.520(8) yes
C(15) C(20) . . 1.393(8) yes
C(17) C(18) . . 1.355(9) yes
C(19) C(20) . . 1.376(8) yes
N(21) C(22) . . 1.409(6) yes
