#------------------------------------------------------------------------------
#$Date: 2020-08-20 07:58:41 +0300 (Thu, 20 Aug 2020) $
#$Revision: 255478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/35/2243549.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_2243549
loop_
_publ_author_name
'Çınar, Emine Berrin'
'Yeşilbağ, Semanur'
'Doğan, Onur Erman'
'Ağar, Erbil'
'Dege, Necmi'
'Saif, Eiad'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 1,7-dimethyl-5a,6,11a,12-tetrahydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine
;
_journal_coeditor_code           YK2135
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1472
_journal_page_last               1475
_journal_paper_doi               10.1107/S2056989020010646
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_melting_point_gt       472
_chemical_melting_point_lt       475
_chemical_name_systematic
1,7-Dimethyl-5a,6,11a,12-tetrahydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.751(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.798(3)
_cell_length_b                   4.7133(4)
_cell_length_c                   11.5330(14)
_cell_measurement_reflns_used    3858
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      1.84
_cell_volume                     1290.8(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
and Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), SHELXL2018/3 (Sheldrick, 2015b),
PLATON (Spek, 2020) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/3 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5580
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.948
_diffrn_reflns_theta_min         3.432
_diffrn_source
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus'
;
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9414
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0639P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1024
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2135sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243549
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.50672(4) 0.7122(2) -0.13429(9) 0.0582(3) Uani d 1 . .
N N1 -0.57174(5) 0.4629(3) -0.34733(13) 0.0622(4) Uani d 1 . .
H H1 -0.591648 0.369876 -0.409012 0.075 Uiso calc 1 . .
C C7 -0.59760(6) 0.6173(3) -0.27650(13) 0.0484(3) Uani d 1 . .
C C2 -0.65643(6) 0.6435(3) -0.30692(14) 0.0531(4) Uani d 1 . .
C C6 -0.56462(6) 0.7472(3) -0.17100(13) 0.0497(3) Uani d 1 . .
C C8 -0.51247(6) 0.4590(3) -0.31772(14) 0.0545(4) Uani d 1 . .
H H8 -0.500090 0.289696 -0.352275 0.065 Uiso calc 1 . .
C C3 -0.67936(7) 0.8104(4) -0.23575(17) 0.0657(5) Uani d 1 . .
H H3 -0.718296 0.828025 -0.255126 0.079 Uiso calc 1 . .
C C5 -0.58834(7) 0.9190(3) -0.10285(15) 0.0599(4) Uani d 1 . .
H H5 -0.565754 1.011706 -0.034970 0.072 Uiso calc 1 . .
C C1 -0.69244(7) 0.4830(4) -0.41332(17) 0.0675(5) Uani d 1 . .
H H1A -0.682704 0.536853 -0.485013 0.101 Uiso calc 1 . .
H H1B -0.731357 0.526107 -0.423392 0.101 Uiso calc 1 . .
H H1C -0.686334 0.283070 -0.399720 0.101 Uiso calc 1 . .
C C4 -0.64605(8) 0.9525(4) -0.13620(18) 0.0709(5) Uani d 1 . .
H H4 -0.662501 1.070905 -0.091513 0.085 Uiso calc 1 . .
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
C6 O1 C8 . 2_454 113.95(11) ?
C7 N1 C8 . . 119.51(12) ?
C7 N1 H1 . . 120.2 ?
C8 N1 H1 . . 120.2 ?
N1 C7 C6 . . 119.38(12) ?
N1 C7 C2 . . 121.63(14) ?
C6 C7 C2 . . 118.98(14) ?
C3 C2 C7 . . 118.72(15) ?
C3 C2 C1 . . 121.82(14) ?
C7 C2 C1 . . 119.43(15) ?
C5 C6 O1 . . 118.20(13) ?
C5 C6 C7 . . 121.14(13) ?
O1 C6 C7 . . 120.64(12) ?
N1 C8 O1 . 2_454 109.28(12) ?
N1 C8 C8 . 2_454 109.82(15) ?
O1 C8 C8 2_454 2_454 108.29(9) ?
N1 C8 H8 . . 109.8 ?
O1 C8 H8 2_454 . 109.8 ?
C8 C8 H8 2_454 . 109.8 ?
C2 C3 C4 . . 121.60(15) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C6 C5 C4 . . 119.27(16) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C4 C5 . . 120.05(16) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
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 C6 . 1.3846(17) ?
O1 C8 2_454 1.4521(18) ?
N1 C7 . 1.3822(19) ?
N1 C8 . 1.4099(19) ?
N1 H1 . 0.8600 ?
C7 C6 . 1.397(2) ?
C7 C2 . 1.4041(19) ?
C2 C3 . 1.373(2) ?
C2 C1 . 1.498(2) ?
C6 C5 . 1.373(2) ?
C8 C8 2_454 1.505(3) ?
C8 H8 . 0.9800 ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C5 C4 . 1.380(2) ?
C5 H5 . 0.9300 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C4 H4 . 0.9300 ?
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
C5 H5 O1 5_475 0.93 2.59 3.513(2) 172 yes
N1 H1 C5 6_565 0.86 2.64 3.375(2) 144 yes
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
C8 N1 C7 C6 . . . . -5.4(2) ?
C8 N1 C7 C2 . . . . 175.60(14) ?
N1 C7 C2 C3 . . . . -177.10(14) ?
C6 C7 C2 C3 . . . . 3.9(2) ?
N1 C7 C2 C1 . . . . 4.7(2) ?
C6 C7 C2 C1 . . . . -174.29(14) ?
C8 O1 C6 C5 2_454 . . . 159.07(13) ?
C8 O1 C6 C7 2_454 . . . -22.75(17) ?
N1 C7 C6 C5 . . . . 175.29(14) ?
C2 C7 C6 C5 . . . . -5.7(2) ?
N1 C7 C6 O1 . . . . -2.8(2) ?
C2 C7 C6 O1 . . . . 176.19(13) ?
C7 N1 C8 O1 . . . 2_454 -82.21(17) ?
C7 N1 C8 C8 . . . 2_454 36.44(15) ?
C7 C2 C3 C4 . . . . 0.3(2) ?
C1 C2 C3 C4 . . . . 178.44(16) ?
O1 C6 C5 C4 . . . . -178.67(14) ?
C7 C6 C5 C4 . . . . 3.2(2) ?
C2 C3 C4 C5 . . . . -2.9(3) ?
C6 C5 C4 C3 . . . . 1.1(2) ?

_cod_database_fobs_code 2243549
