#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017585.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_2017585
loop_
_publ_author_name
'Acosta, Lina M.'
'Palma, Alirio'
'Bahsas, Ali'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen-bonded dimers, chains and rings in six differently
 substituted 2-vinyltetrahydro-1,4-epoxy-1-benzazepines
;
_journal_coeditor_code           SK3373
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o209
_journal_page_last               o214
_journal_paper_doi               10.1107/S0108270110009017
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H13 N O'
_chemical_formula_moiety         'C12 H13 N O'
_chemical_formula_sum            'C12 H13 N O'
_chemical_formula_weight         187.23
_chemical_name_systematic
;
(2SR,4RS)-2-exo-vinyl-2,3,4,5-tetrahydro-1H-
1,4-epoxy-1-benzazepine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.441(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8070(13)
_cell_length_b                   7.3982(7)
_cell_length_c                   13.738(2)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.96
_cell_volume                     960.8(2)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13902
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0467P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                1488
_reflns_number_total             2200
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3373.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017585
_cod_database_fobs_code          2017585
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O14 0.49055(10) 0.45113(14) 0.10465(8) 0.0253(3) Uani d . 1 . .
N N1 0.57935(12) 0.40949(16) 0.20407(9) 0.0207(3) Uani d . 1 . .
C C2 0.67762(15) 0.2748(2) 0.18020(12) 0.0214(3) Uani d . 1 . .
H H2 0.7176 0.1959 0.2401 0.026 Uiso calc R 1 . .
C C3 0.58270(16) 0.1630(2) 0.09360(12) 0.0261(4) Uani d . 1 . .
H H3A 0.6278 0.1473 0.0377 0.031 Uiso calc R 1 . .
H H3B 0.5624 0.0425 0.1178 0.031 Uiso calc R 1 . .
C C4 0.44854(16) 0.2754(2) 0.06014(12) 0.0262(4) Uani d . 1 . .
H H4 0.4170 0.2843 -0.0152 0.031 Uiso calc R 1 . .
C C5 0.32915(15) 0.2113(2) 0.10149(12) 0.0266(4) Uani d . 1 . .
H H5A 0.2420 0.2797 0.0696 0.032 Uiso calc R 1 . .
H H5B 0.3107 0.0815 0.0857 0.032 Uiso calc R 1 . .
C C5a 0.36800(14) 0.2388(2) 0.21397(12) 0.0220(3) Uani d . 1 . .
C C6 0.28380(15) 0.1747(2) 0.27298(12) 0.0254(4) Uani d . 1 . .
H H6 0.1982 0.1133 0.2417 0.031 Uiso calc R 1 . .
C C7 0.32186(16) 0.1984(2) 0.37583(13) 0.0286(4) Uani d . 1 . .
H H7 0.2625 0.1542 0.4150 0.034 Uiso calc R 1 . .
C C8 0.44640(16) 0.2864(2) 0.42228(12) 0.0285(4) Uani d . 1 . .
H H8 0.4738 0.3005 0.4936 0.034 Uiso calc R 1 . .
C C9 0.53088(15) 0.3537(2) 0.36484(12) 0.0242(4) Uani d . 1 . .
H H9 0.6160 0.4157 0.3963 0.029 Uiso calc R 1 . .
C C9a 0.49104(14) 0.33046(19) 0.26153(11) 0.0199(3) Uani d . 1 . .
C C21 0.79369(16) 0.3709(2) 0.15017(12) 0.0255(4) Uani d . 1 . .
H H21 0.7684 0.4580 0.0977 0.031 Uiso calc R 1 . .
C C22 0.92861(16) 0.3425(2) 0.19176(13) 0.0312(4) Uani d . 1 . .
H H22A 0.9573 0.2562 0.2445 0.037 Uiso calc R 1 . .
H H22B 0.9976 0.4082 0.1692 0.037 Uiso calc R 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
N1 O14 C4 . . 103.88(10) ?
C9a N1 O14 . . 107.78(10) ?
C9a N1 C2 . . 111.67(11) ?
O14 N1 C2 . . 101.42(10) ?
N1 C2 C21 . . 109.30(12) ?
N1 C2 C3 . . 103.70(11) ?
C21 C2 C3 . . 113.02(12) ?
N1 C2 H2 . . 110.2 ?
C21 C2 H2 . . 110.2 ?
C3 C2 H2 . . 110.2 ?
C4 C3 C2 . . 103.64(12) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O14 C4 C5 . . 106.59(12) ?
O14 C4 C3 . . 103.72(11) ?
C5 C4 C3 . . 114.21(13) ?
O14 C4 H4 . . 110.7 ?
C5 C4 H4 . . 110.7 ?
C3 C4 H4 . . 110.7 ?
C5a C5 C4 . . 109.56(12) ?
C5a C5 H5A . . 109.8 ?
C4 C5 H5A . . 109.8 ?
C5a C5 H5B . . 109.8 ?
C4 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.2 ?
C6 C5a C9a . . 118.10(14) ?
C6 C5a C5 . . 121.82(13) ?
C9a C5a C5 . . 120.08(13) ?
C7 C6 C5a . . 121.15(14) ?
C7 C6 H6 . . 119.4 ?
C5a C6 H6 . . 119.4 ?
C6 C7 C8 . . 120.01(14) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 119.83(15) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C9a C9 C8 . . 119.66(14) ?
C9a C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C9a C5a . . 121.23(14) ?
C9 C9a N1 . . 117.78(13) ?
C5a C9a N1 . . 120.96(13) ?
C22 C21 C2 . . 124.03(16) ?
C22 C21 H21 . . 118.0 ?
C2 C21 H21 . . 118.0 ?
C21 C22 H22A . . 120.0 ?
C21 C22 H22B . . 120.0 ?
H22A C22 H22B . . 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
O14 N1 . 1.4441(15) ?
O14 C4 . 1.4488(18) ?
N1 C9a . 1.4419(18) ?
N1 C2 . 1.4822(18) ?
C2 C21 . 1.490(2) ?
C2 C3 . 1.542(2) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.521(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.508(2) ?
C4 H4 . 1.0000 ?
C5 C5a . 1.504(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5a C6 . 1.386(2) ?
C5a C9a . 1.387(2) ?
C6 C7 . 1.373(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.381(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.380(2) ?
C8 H8 . 0.9500 ?
C9 C9a . 1.379(2) ?
C9 H9 . 0.9500 ?
C21 C22 . 1.311(2) ?
C21 H21 . 0.9500 ?
C22 H22A . 0.9500 ?
C22 H22B . 0.9500 ?
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
C4 H4 O14 3_665 1.00 2.60 3.209(2) 119 no
C6 H6 Cg1 2_545 0.95 2.83 3.616(2) 141 no
C22 H22B Cg1 2_655 0.95 2.78 3.529(2) 136 no
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
C4 O14 N1 C9a . . . . -67.70(13) ?
C4 O14 N1 C2 . . . . 49.71(12) ?
C9a N1 C2 C21 . . . . -162.66(12) ?
O14 N1 C2 C21 . . . . 82.79(13) ?
C9a N1 C2 C3 . . . . 76.55(14) ?
O14 N1 C2 C3 . . . . -38.00(13) ?
N1 C2 C3 C4 . . . . 13.57(15) ?
C21 C2 C3 C4 . . . . -104.67(14) ?
N1 O14 C4 C5 . . . . 80.17(13) ?
N1 O14 C4 C3 . . . . -40.70(13) ?
C2 C3 C4 O14 . . . . 15.76(15) ?
C2 C3 C4 C5 . . . . -99.84(14) ?
O14 C4 C5 C5a . . . . -46.92(16) ?
C3 C4 C5 C5a . . . . 66.99(17) ?
C4 C5 C5a C6 . . . . -173.27(14) ?
C4 C5 C5a C9a . . . . 6.71(19) ?
C9a C5a C6 C7 . . . . -1.1(2) ?
C5 C5a C6 C7 . . . . 178.92(14) ?
C5a C6 C7 C8 . . . . -0.4(2) ?
C6 C7 C8 C9 . . . . 1.3(2) ?
C7 C8 C9 C9a . . . . -0.8(2) ?
C8 C9 C9a C5a . . . . -0.7(2) ?
C8 C9 C9a N1 . . . . 177.46(13) ?
C6 C5a C9a C9 . . . . 1.6(2) ?
C5 C5a C9a C9 . . . . -178.38(14) ?
C6 C5a C9a N1 . . . . -176.48(13) ?
C5 C5a C9a N1 . . . . 3.5(2) ?
O14 N1 C9a C9 . . . . -151.29(12) ?
C2 N1 C9a C9 . . . . 98.15(15) ?
O14 N1 C9a C5a . . . . 26.85(17) ?
C2 N1 C9a C5a . . . . -83.71(16) ?
N1 C2 C21 C22 . . . . 126.62(16) ?
C3 C2 C21 C22 . . . . -118.46(17) ?
