#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017611.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_2017611
loop_
_publ_author_name
'Acosta, Lina M.'
'Palma, Alirio'
'Bahsas, Ali'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 A three-dimensional hydrogen-bonded framework in
 (2S*,4R*)-7-fluoro-2-exo-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_journal_coeditor_code           GG3231
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o206
_journal_page_last               o208
_journal_paper_doi               10.1107/S010827011000884X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H16 F N O'
_chemical_formula_moiety         'C18 H16 F N O'
_chemical_formula_sum            'C18 H16 F N O'
_chemical_formula_weight         281.32
_chemical_name_systematic
;
(2S,4R)-7-fluoro-2-exo-[(E)-styryl]-2,3,4,5-\
tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.10(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.052(4)
_cell_length_b                   5.299(4)
_cell_length_c                   12.976(8)
_cell_measurement_reflns_used    1432
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      3.71
_cell_volume                     691.0(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9381
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1432
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0493
_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)+(0.0469P)²+0.2187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1112
_reflns_number_total             1432
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3231.cif
_cod_data_source_block           I
_cod_original_cell_volume        691.1(7)
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017611
_cod_database_fobs_code          2017611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
F F7 1.2068(2) 0.7113(6) 0.66422(18) 0.0375(7) Uani d . 1 . .
O O14 0.6429(2) 0.3291(5) 0.5663(2) 0.0237(6) Uani d . 1 . .
N N1 0.7007(3) 0.3167(6) 0.6689(2) 0.0211(7) Uani d . 1 . .
C C2 0.6123(4) 0.4842(8) 0.7281(3) 0.0222(9) Uani d . 1 . .
H H2 0.6646 0.5663 0.7853 0.027 Uiso calc R 1 . .
C C3 0.5668(4) 0.6859(8) 0.6496(3) 0.0268(10) Uani d . 1 . .
H H3A 0.4685 0.6951 0.6452 0.032 Uiso calc R 1 . .
H H3B 0.6023 0.8540 0.6689 0.032 Uiso calc R 1 . .
C C4 0.6231(4) 0.5981(8) 0.5494(3) 0.0253(10) Uani d . 1 . .
H H4 0.5572 0.6263 0.4918 0.030 Uiso calc R 1 . .
C C5 0.7551(3) 0.7126(9) 0.5234(3) 0.0231(9) Uani d . 1 . .
H H5A 0.7789 0.6657 0.4522 0.028 Uiso calc R 1 . .
H H5B 0.7494 0.8988 0.5273 0.028 Uiso calc R 1 . .
C C5A 0.8606(3) 0.6182(8) 0.5982(3) 0.0193(8) Uani d . 1 . .
C C6 0.9886(3) 0.7139(8) 0.5984(3) 0.0232(9) Uani d . 1 . .
H H6 1.0114 0.8480 0.5535 0.028 Uiso calc R 1 . .
C C7 1.0816(4) 0.6123(9) 0.6644(3) 0.0260(10) Uani d . 1 . .
C C8 1.0558(4) 0.4192(8) 0.7296(3) 0.0270(10) Uani d . 1 . .
H H8 1.1233 0.3537 0.7743 0.032 Uiso calc R 1 . .
C C9 0.9288(3) 0.3207(8) 0.7292(3) 0.0216(8) Uani d . 1 . .
H H9 0.9079 0.1836 0.7732 0.026 Uiso calc R 1 . .
C C9A 0.8323(3) 0.4219(7) 0.6646(3) 0.0181(8) Uani d . 1 . .
C C21 0.4991(3) 0.3389(9) 0.7722(3) 0.0227(9) Uani d . 1 . .
H H21 0.4501 0.2273 0.7285 0.027 Uiso calc R 1 . .
C C22 0.4647(3) 0.3599(8) 0.8694(3) 0.0240(9) Uani d . 1 . .
H H22 0.5189 0.4650 0.9121 0.029 Uiso calc R 1 . .
C C221 0.3520(3) 0.2382(8) 0.9179(3) 0.0216(9) Uani d . 1 . .
C C222 0.2934(4) 0.0213(8) 0.8775(3) 0.0238(9) Uani d . 1 . .
H H222 0.3295 -0.0563 0.8183 0.029 Uiso calc R 1 . .
C C223 0.1830(4) -0.0822(8) 0.9229(3) 0.0276(10) Uani d . 1 . .
H H223 0.1426 -0.2283 0.8936 0.033 Uiso calc R 1 . .
C C224 0.1309(4) 0.0237(8) 1.0098(3) 0.0267(10) Uani d . 1 . .
H H224 0.0550 -0.0488 1.0406 0.032 Uiso calc R 1 . .
C C225 0.1897(4) 0.2361(9) 1.0521(3) 0.0286(10) Uani d . 1 . .
H H225 0.1547 0.3099 1.1126 0.034 Uiso calc R 1 . .
C C226 0.2990(4) 0.3403(9) 1.0064(3) 0.0249(9) Uani d . 1 . .
H H226 0.3393 0.4858 1.0363 0.030 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'
F F 0.0171 0.0103 '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 . . 103.6(3) ?
C9A N1 O14 . . 107.5(3) ?
C9A N1 C2 . . 110.5(3) ?
O14 N1 C2 . . 102.5(3) ?
N1 C2 C21 . . 111.0(3) ?
N1 C2 C3 . . 104.2(3) ?
C21 C2 C3 . . 113.0(3) ?
N1 C2 H2 . . 109.5 ?
C21 C2 H2 . . 109.5 ?
C3 C2 H2 . . 109.5 ?
C4 C3 C2 . . 104.2(3) ?
C4 C3 H3A . . 110.9 ?
C2 C3 H3A . . 110.9 ?
C4 C3 H3B . . 110.9 ?
C2 C3 H3B . . 110.9 ?
H3A C3 H3B . . 108.9 ?
O14 C4 C3 . . 103.0(3) ?
O14 C4 C5 . . 108.1(3) ?
C3 C4 C5 . . 114.7(4) ?
O14 C4 H4 . . 110.2 ?
C3 C4 H4 . . 110.2 ?
C5 C4 H4 . . 110.2 ?
C4 C5 C5A . . 109.5(3) ?
C4 C5 H5B . . 109.8 ?
C5A C5 H5B . . 109.8 ?
C4 C5 H5A . . 109.8 ?
C5A C5 H5A . . 109.8 ?
H5A C5 H5B . . 108.2 ?
C9A C5A C6 . . 118.5(3) ?
C9A C5A C5 . . 120.0(3) ?
C6 C5A C5 . . 121.5(4) ?
C7 C6 C5A . . 118.8(4) ?
C7 C6 H6 . . 120.6 ?
C5A C6 H6 . . 120.6 ?
C8 C7 F7 . . 118.6(4) ?
C8 C7 C6 . . 123.5(4) ?
F7 C7 C6 . . 117.9(4) ?
C7 C8 C9 . . 118.1(4) ?
C7 C8 H8 . . 121.0 ?
C9 C8 H8 . . 121.0 ?
C9A C9 C8 . . 119.7(4) ?
C9A C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C9A C5A . . 121.4(3) ?
C9 C9A N1 . . 117.6(3) ?
C5A C9A N1 . . 121.1(3) ?
C22 C21 C2 . . 122.5(4) ?
C22 C21 H21 . . 118.8 ?
C2 C21 H21 . . 118.8 ?
C21 C22 C221 . . 126.5(4) ?
C21 C22 H22 . . 116.7 ?
C221 C22 H22 . . 116.7 ?
C226 C221 C222 . . 117.9(4) ?
C226 C221 C22 . . 120.0(4) ?
C222 C221 C22 . . 122.1(4) ?
C223 C222 C221 . . 120.4(4) ?
C223 C222 H222 . . 119.8 ?
C221 C222 H222 . . 119.8 ?
C224 C223 C222 . . 120.7(4) ?
C224 C223 H223 . . 119.6 ?
C222 C223 H223 . . 119.6 ?
C223 C224 C225 . . 119.6(4) ?
C223 C224 H224 . . 120.2 ?
C225 C224 H224 . . 120.2 ?
C226 C225 C224 . . 119.7(4) ?
C226 C225 H225 . . 120.1 ?
C224 C225 H225 . . 120.1 ?
C225 C226 C221 . . 121.6(4) ?
C225 C226 H226 . . 119.2 ?
C221 C226 H226 . . 119.2 ?
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
F7 C7 . 1.363(4) ?
O14 N1 . 1.443(4) ?
O14 C4 . 1.455(5) ?
N1 C9A . 1.437(4) ?
N1 C2 . 1.481(5) ?
C2 C21 . 1.497(5) ?
C2 C3 . 1.540(6) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.502(6) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.504(5) ?
C4 H4 . 1.0000 ?
C5 C5A . 1.509(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5A C9A . 1.383(5) ?
C5A C6 . 1.383(5) ?
C6 C7 . 1.366(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.356(6) ?
C8 C9 . 1.379(5) ?
C8 H8 . 0.9500 ?
C9 C9A . 1.379(5) ?
C9 H9 . 0.9500 ?
C21 C22 . 1.319(5) ?
C21 H21 . 0.9500 ?
C22 C221 . 1.457(5) ?
C22 H22 . 0.9500 ?
C221 C226 . 1.386(5) ?
C221 C222 . 1.390(6) ?
C222 C223 . 1.379(5) ?
C222 H222 . 0.9500 ?
C223 C224 . 1.373(6) ?
C223 H223 . 0.9500 ?
C224 C225 . 1.380(6) ?
C224 H224 . 0.9500 ?
C225 C226 . 1.374(6) ?
C225 H225 . 0.9500 ?
C226 H226 . 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 2_656 1.00 2.39 3.278(5) 148 y
C5 H5B O14 1_565 0.99 2.57 3.504(6) 157 y
C6 H6 Cg1 2_756 0.95 2.98 3.815(5) 147 y
C8 H8 Cg2 1_655 0.95 2.97 3.860(5) 158 y
C22 H22 Cg2 2_657 0.95 3.00 3.896(5) 158 y
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 . . . . -68.9(3) ?
C4 O14 N1 C2 . . . . 47.5(3) ?
C9A N1 C2 C21 . . . . -155.6(3) ?
O14 N1 C2 C21 . . . . 90.1(3) ?
C9A N1 C2 C3 . . . . 82.5(3) ?
O14 N1 C2 C3 . . . . -31.8(3) ?
N1 C2 C3 C4 . . . . 5.6(4) ?
C21 C2 C3 C4 . . . . -115.0(4) ?
N1 O14 C4 C3 . . . . -43.6(3) ?
N1 O14 C4 C5 . . . . 78.2(4) ?
C2 C3 C4 O14 . . . . 22.4(4) ?
C2 C3 C4 C5 . . . . -94.8(4) ?
O14 C4 C5 C5A . . . . -46.4(4) ?
C3 C4 C5 C5A . . . . 67.9(5) ?
C4 C5 C5A C9A . . . . 10.5(5) ?
C4 C5 C5A C6 . . . . -173.2(4) ?
C9A C5A C6 C7 . . . . -0.4(5) ?
C5 C5A C6 C7 . . . . -176.7(4) ?
C5A C6 C7 C8 . . . . 0.7(6) ?
C5A C6 C7 F7 . . . . -179.3(4) ?
F7 C7 C8 C9 . . . . 180.0(4) ?
C6 C7 C8 C9 . . . . 0.0(6) ?
C7 C8 C9 C9A . . . . -1.0(6) ?
C8 C9 C9A C5A . . . . 1.3(6) ?
C8 C9 C9A N1 . . . . -178.5(4) ?
C6 C5A C9A C9 . . . . -0.6(5) ?
C5 C5A C9A C9 . . . . 175.8(4) ?
C6 C5A C9A N1 . . . . 179.1(4) ?
C5 C5A C9A N1 . . . . -4.5(5) ?
O14 N1 C9A C9 . . . . -146.5(3) ?
C2 N1 C9A C9 . . . . 102.4(4) ?
O14 N1 C9A C5A . . . . 33.7(4) ?
C2 N1 C9A C5A . . . . -77.4(4) ?
N1 C2 C21 C22 . . . . 131.8(4) ?
C3 C2 C21 C22 . . . . -111.5(4) ?
C2 C21 C22 C221 . . . . 176.3(4) ?
C21 C22 C221 C226 . . . . -157.0(4) ?
C21 C22 C221 C222 . . . . 22.3(6) ?
C226 C221 C222 C223 . . . . 2.3(5) ?
C22 C221 C222 C223 . . . . -177.1(4) ?
C221 C222 C223 C224 . . . . -1.4(6) ?
C222 C223 C224 C225 . . . . 0.1(6) ?
C223 C224 C225 C226 . . . . 0.4(6) ?
C224 C225 C226 C221 . . . . 0.4(6) ?
C222 C221 C226 C225 . . . . -1.8(5) ?
C22 C221 C226 C225 . . . . 177.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726629
