#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208436.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_2208436
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Özdamar, Özgür'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2,2-Dimethyl-1,4-dihydro-2H-3,1-benzoxazine
;
_journal_coeditor_code           TK6304
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o908
_journal_page_last               o910
_journal_paper_doi               10.1107/S1600536806003825
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H13 N O'
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_chemical_melting_point          391.0(10)
_chemical_name_systematic
;
2,2-Dimethyl-1,4-dihydro-2H-3,1-benzoxazine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2844(9)
_cell_length_b                   8.4743(10)
_cell_length_c                   25.388(3)
_cell_measurement_reflns_used    9459
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.6
_cell_volume                     1782.4(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.069
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9973
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.81
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.81
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0275P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.057
_refine_ls_wR_factor_ref         0.061
_reflns_number_gt                2027
_reflns_number_total             3493
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6304.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '390-392' was changed to '391.0(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 '390-392' was changed to '391.0(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               2208436
_cod_database_fobs_code          2208436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
C2 0.2423(2) 0.43580(19) 0.50430(7) 0.0428(5) Uani d . 1 C
C3 0.2809(2) 0.2842(2) 0.48673(9) 0.0536(6) Uani d . 1 C
H3 0.3487 0.2212 0.5070 0.064 Uiso calc R 1 H
C4 0.2211(2) 0.2266(2) 0.44033(9) 0.0574(6) Uani d . 1 C
H4 0.2460 0.1245 0.4297 0.069 Uiso calc R 1 H
C5 0.1238(2) 0.3205(2) 0.40945(8) 0.0545(5) Uani d . 1 C
H5 0.0842 0.2822 0.3776 0.065 Uiso calc R 1 H
C6 0.0850(2) 0.4708(2) 0.42557(8) 0.0481(5) Uani d . 1 C
H6 0.0195 0.5337 0.4045 0.058 Uiso calc R 1 H
C1 0.1429(2) 0.5293(2) 0.47302(8) 0.0410(5) Uani d . 1 C
C7 0.3088(2) 0.49964(19) 0.55490(9) 0.0540(5) Uani d . 1 C
H7A 0.2520 0.4520 0.5843 0.065 Uiso calc R 1 H
H7B 0.4219 0.4715 0.5578 0.065 Uiso calc R 1 H
C8 0.1344(2) 0.7235(2) 0.54357(8) 0.0468(5) Uani d . 1 C
C9 0.0072(2) 0.6542(3) 0.57970(9) 0.0702(6) Uani d . 1 C
H9A 0.0000 0.5425 0.5739 0.105 Uiso calc R 1 H
H9B -0.0953 0.7022 0.5724 0.105 Uiso calc R 1 H
H9C 0.0364 0.6740 0.6157 0.105 Uiso calc R 1 H
C10 0.1431(3) 0.9008(2) 0.54919(10) 0.0732(7) Uani d . 1 C
H10A 0.1654 0.9275 0.5852 0.110 Uiso calc R 1 H
H10B 0.0419 0.9464 0.5388 0.110 Uiso calc R 1 H
H10C 0.2276 0.9411 0.5271 0.110 Uiso calc R 1 H
C12 0.1848(2) 0.3428(2) 0.74965(7) 0.0418(5) Uani d . 1 C
C13 0.0336(2) 0.3841(2) 0.73077(9) 0.0535(6) Uani d . 1 C
H13 -0.0289 0.4555 0.7497 0.064 Uiso calc R 1 H
C14 -0.0257(2) 0.3221(2) 0.68491(9) 0.0586(6) Uani d . 1 C
H14 -0.1286 0.3490 0.6734 0.070 Uiso calc R 1 H
C15 0.0682(3) 0.2194(2) 0.65587(8) 0.0553(6) Uani d . 1 C
H15 0.0290 0.1781 0.6244 0.066 Uiso calc R 1 H
C16 0.2192(2) 0.1781(2) 0.67323(8) 0.0476(5) Uani d . 1 C
H16 0.2820 0.1092 0.6534 0.057 Uiso calc R 1 H
C11 0.2790(2) 0.2385(2) 0.72043(8) 0.0418(5) Uani d . 1 C
C17 0.2497(2) 0.4095(2) 0.80014(8) 0.0517(5) Uani d . 1 C
H17A 0.2235 0.5209 0.8021 0.062 Uiso calc R 1 H
H17B 0.1985 0.3570 0.8297 0.062 Uiso calc R 1 H
C18 0.4746(2) 0.2324(2) 0.79251(8) 0.0460(5) Uani d . 1 C
C19 0.3971(3) 0.1150(2) 0.82999(9) 0.0675(6) Uani d . 1 C
H19A 0.4168 0.1472 0.8657 0.101 Uiso calc R 1 H
H19B 0.4428 0.0123 0.8243 0.101 Uiso calc R 1 H
H19C 0.2829 0.1113 0.8237 0.101 Uiso calc R 1 H
C20 0.6550(2) 0.2364(2) 0.79908(9) 0.0657(6) Uani d . 1 C
H20A 0.7002 0.3132 0.7755 0.099 Uiso calc R 1 H
H20B 0.6989 0.1342 0.7912 0.099 Uiso calc R 1 H
H20C 0.6811 0.2642 0.8347 0.099 Uiso calc R 1 H
N1 0.1082(2) 0.68361(17) 0.48884(7) 0.0490(4) Uani d . 1 N
N2 0.4343(2) 0.20138(19) 0.73751(7) 0.0484(4) Uani d . 1 N
O1 0.29252(14) 0.66850(14) 0.55770(5) 0.0487(3) Uani d . 1 O
O2 0.42080(16) 0.39010(13) 0.80384(5) 0.0469(3) Uani d . 1 O
H1N 0.017(2) 0.721(2) 0.4759(8) 0.051(6) Uiso d . 1 H
H2N 0.478(3) 0.114(3) 0.7252(8) 0.079(8) Uiso 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
_geom_angle_publ_flag
C7 O1 C8 113.33(14) y
C17 O2 C18 113.63(14) y
C1 N1 C8 117.64(16) y
C11 N2 C18 117.91(17) y
C1 C2 C3 118.48(18) ?
C1 C2 C7 120.07(16) ?
C3 C2 C7 121.42(17) ?
C4 C3 C2 121.33(19) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
C3 C4 C5 119.74(18) ?
C3 C4 H4 120.1 ?
C5 C4 H4 120.1 ?
C6 C5 C4 120.1(2) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C5 C6 C1 120.52(19) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
C6 C1 C2 119.77(17) ?
C6 C1 N1 120.81(18) ?
C2 C1 N1 119.37(18) ?
O1 C7 C2 111.53(16) y
O1 C7 H7A 109.3 ?
C2 C7 H7A 109.3 ?
O1 C7 H7B 109.3 ?
C2 C7 H7B 109.3 ?
H7A C7 H7B 108.0 ?
O1 C8 N1 107.51(16) y
O1 C8 C9 110.92(15) y
O1 C8 C10 104.84(17) y
N1 C8 C9 112.72(17) y
N1 C8 C10 109.30(18) y
C9 C8 C10 111.20(19) y
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C13 C12 C11 118.86(18) ?
C13 C12 C17 121.60(17) ?
C11 C12 C17 119.54(17) ?
C14 C13 C12 121.41(19) ?
C14 C13 H13 119.3 ?
C12 C13 H13 119.3 ?
C13 C14 C15 119.62(19) ?
C13 C14 H14 120.2 ?
C15 C14 H14 120.2 ?
C16 C15 C14 120.2(2) ?
C16 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C15 C16 C11 120.43(19) ?
C15 C16 H16 119.8 ?
C11 C16 H16 119.8 ?
C12 C11 N2 119.66(18) ?
C12 C11 C16 119.45(19) ?
N2 C11 C16 120.83(18) ?
O2 C17 C12 111.60(15) ?
O2 C17 H17A 109.3 ?
C12 C17 H17A 109.3 ?
O2 C17 H17B 109.3 ?
C12 C17 H17B 109.3 ?
H17A C17 H17B 108.0 ?
O2 C18 N2 106.73(15) ?
O2 C18 C20 105.37(16) ?
N2 C18 C20 109.72(18) ?
O2 C18 C19 110.65(16) ?
N2 C18 C19 112.62(16) ?
C20 C18 C19 111.40(18) ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C18 C20 H20A 109.5 ?
C18 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C18 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C1 N1 H1N 114.0(12) ?
C8 N1 H1N 113.7(12) ?
C11 N2 H2N 117.4(15) ?
C18 N2 H2N 113.3(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C1 1.391(2) ?
C2 C3 1.397(2) ?
C2 C7 1.499(3) ?
C3 C4 1.368(3) ?
C3 H3 0.9300 ?
C4 C5 1.377(3) ?
C4 H4 0.9300 ?
C5 C6 1.376(2) ?
C5 H5 0.9300 ?
C6 C1 1.388(2) ?
C6 H6 0.9300 ?
C1 N1 1.398(2) y
C7 O1 1.439(2) y
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 O1 1.436(2) y
C8 N1 1.447(2) y
C8 C10 1.510(2) ?
C8 C9 1.515(3) ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C12 C13 1.386(3) ?
C12 C11 1.393(2) ?
C12 C17 1.501(3) ?
C13 C14 1.369(3) ?
C13 H13 0.9300 ?
C14 C15 1.381(3) ?
C14 H14 0.9300 ?
C15 C16 1.371(3) ?
C15 H15 0.9300 ?
C16 C11 1.394(3) ?
C16 H16 0.9300 ?
C11 N2 1.394(2) y
C17 O2 1.430(2) y
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 O2 1.438(2) y
C18 N2 1.460(3) y
C18 C20 1.504(3) ?
C18 C19 1.519(3) ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
N1 H1N 0.882(19) ?
N2 H2N 0.88(2) ?
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
N1 H1N O1 3_466 0.882(19) 2.25(2) 3.131(2) 176.5(17)
N2 H2N O2 4_646 0.88(2) 2.20(2) 3.082(2) 177(2)
C20 H20C O1 4_646 0.96 2.86 3.707(3) 148
C6 H6 O2 2_564 0.93 2.68 3.308(2) 125
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
C1 C2 C3 C4 -1.1(3)
C7 C2 C3 C4 -179.48(19)
C2 C3 C4 C5 1.6(3)
C3 C4 C5 C6 -0.9(3)
C4 C5 C6 C1 -0.2(3)
C5 C6 C1 C2 0.6(3)
C5 C6 C1 N1 177.95(18)
C3 C2 C1 C6 0.0(3)
C7 C2 C1 C6 178.39(17)
C3 C2 C1 N1 -177.38(18)
C7 C2 C1 N1 1.0(3)
C1 C2 C7 O1 -15.1(3)
C3 C2 C7 O1 163.27(17)
C11 C12 C13 C14 1.5(3)
C17 C12 C13 C14 -179.51(19)
C12 C13 C14 C15 -1.8(3)
C13 C14 C15 C16 0.9(3)
C14 C15 C16 C11 0.3(3)
C13 C12 C11 N2 176.99(18)
C17 C12 C11 N2 -2.0(3)
C13 C12 C11 C16 -0.2(3)
C17 C12 C11 C16 -179.28(17)
C15 C16 C11 C12 -0.6(3)
C15 C16 C11 N2 -177.84(18)
C13 C12 C17 O2 -162.33(17)
C11 C12 C17 O2 16.7(2)
C6 C1 N1 C8 164.01(18)
C2 C1 N1 C8 -18.7(3)
O1 C8 N1 C1 48.5(2)
C10 C8 N1 C1 161.79(18)
C9 C8 N1 C1 -74.0(2)
C12 C11 N2 C18 18.7(2)
C16 C11 N2 C18 -164.09(16)
O2 C18 N2 C11 -47.8(2)
C20 C18 N2 C11 -161.47(17)
C19 C18 N2 C11 73.8(2)
N1 C8 O1 C7 -63.90(19)
C10 C8 O1 C7 179.86(17)
C9 C8 O1 C7 59.7(2)
C2 C7 O1 C8 47.5(2)
C12 C17 O2 C18 -49.1(2)
N2 C18 O2 C17 64.0(2)
C20 C18 O2 C17 -179.35(16)
C19 C18 O2 C17 -58.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21373903
