#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017839.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017839
loop_
_publ_author_name
'Sanabria, Carlos M.'
'Gómez, Sandra L.'
'Palma, Alirio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Four 1-naphthyl-substituted tetrahydro-1,4-epoxy-1-benzazepines:
 hydrogen-bonded structures in one, two and three dimensions
;
_journal_coeditor_code           GG3246
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o540
_journal_page_last               o546
_journal_paper_doi               10.1107/S0108270110038230
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H16 F3 N O2'
_chemical_formula_moiety         'C21 H16 F3 N O2'
_chemical_formula_sum            'C21 H16 F3 N O2'
_chemical_formula_weight         371.35
_chemical_name_systematic
;
(2S*,4R*)-2-exo-(1-Naphthyl)-7-trifluoromethyl-2,3,4,5-
tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2209(5)
_cell_length_b                   13.140(2)
_cell_length_c                   17.559(2)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.05
_cell_volume                     1666.0(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20342
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0399
_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)+(0.0334P)²+0.5461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                1899
_reflns_number_total             2193
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3246.cif
_cod_data_source_block           III
_cod_database_code               2017839
_cod_database_fobs_code          2017839
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_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
N N1 0.4649(3) 0.53538(15) 0.65449(11) 0.0223(4) Uani d . 1 . .
C C2 0.5316(3) 0.58817(18) 0.58600(12) 0.0207(5) Uani d . 1 . .
H H2 0.5534 0.6617 0.5977 0.025 Uiso calc R 1 . .
C C3 0.7178(3) 0.5351(2) 0.56863(14) 0.0272(6) Uani d . 1 . .
H H3A 0.7301 0.5200 0.5136 0.033 Uiso calc R 1 . .
H H3B 0.8238 0.5776 0.5850 0.033 Uiso calc R 1 . .
C C4 0.7060(4) 0.4379(2) 0.61518(15) 0.0327(6) Uani d . 1 . .
H H4 0.7414 0.3777 0.5836 0.039 Uiso calc R 1 . .
C C5 0.8168(4) 0.4404(2) 0.68826(15) 0.0342(7) Uani d . 1 . .
H H5A 0.8160 0.3724 0.7125 0.041 Uiso calc R 1 . .
H H5B 0.9468 0.4592 0.6772 0.041 Uiso calc R 1 . .
C C5a 0.7312(4) 0.51751(18) 0.74093(13) 0.0235(5) Uani d . 1 . .
C C6 0.8150(4) 0.54313(18) 0.80913(13) 0.0227(5) Uani d . 1 . .
H H6 0.9230 0.5082 0.8256 0.027 Uiso calc R 1 . .
C C7 0.7408(3) 0.61918(18) 0.85249(12) 0.0209(5) Uani d . 1 . .
O O7 0.8235(2) 0.64146(13) 0.92370(8) 0.0242(4) Uani d . 1 . .
C C71 0.9577(4) 0.71102(19) 0.92242(13) 0.0260(6) Uani d . 1 . .
F F71 1.0164(3) 0.72417(13) 0.99247(8) 0.0445(5) Uani d . 1 . .
F F72 1.1013(2) 0.68440(13) 0.88031(9) 0.0367(4) Uani d . 1 . .
F F73 0.9012(2) 0.80003(11) 0.89604(9) 0.0389(4) Uani d . 1 . .
C C8 0.5827(4) 0.67079(18) 0.83186(13) 0.0237(5) Uani d . 1 . .
H H8 0.5360 0.7248 0.8622 0.028 Uiso calc R 1 . .
C C9 0.4946(4) 0.64182(18) 0.76608(12) 0.0224(5) Uani d . 1 . .
H H9 0.3832 0.6748 0.7513 0.027 Uiso calc R 1 . .
C C9a 0.5667(3) 0.56517(17) 0.72132(12) 0.0205(5) Uani d . 1 . .
O O14 0.5137(3) 0.43151(13) 0.63794(10) 0.0294(4) Uani d . 1 . .
C C21 0.3953(3) 0.57850(17) 0.52122(12) 0.0197(5) Uani d . 1 . .
C C22 0.2493(4) 0.5131(2) 0.52548(13) 0.0248(5) Uani d . 1 . .
H H22 0.2309 0.4746 0.5706 0.030 Uiso calc R 1 . .
C C23 0.1255(4) 0.5014(2) 0.46459(14) 0.0291(6) Uani d . 1 . .
H H23 0.0254 0.4548 0.4688 0.035 Uiso calc R 1 . .
C C24 0.1475(4) 0.5560(2) 0.39974(14) 0.0281(6) Uani d . 1 . .
H H24 0.0623 0.5478 0.3589 0.034 Uiso calc R 1 . .
C C25 0.2949(3) 0.62437(19) 0.39263(13) 0.0239(5) Uani d . 1 . .
C C26 0.3213(4) 0.6812(2) 0.32503(14) 0.0300(6) Uani d . 1 . .
H H26 0.2371 0.6731 0.2839 0.036 Uiso calc R 1 . .
C C27 0.4646(4) 0.7468(2) 0.31808(15) 0.0330(6) Uani d . 1 . .
H H27 0.4804 0.7842 0.2722 0.040 Uiso calc R 1 . .
C C28 0.5894(4) 0.7596(2) 0.37814(15) 0.0318(6) Uani d . 1 . .
H H28 0.6893 0.8062 0.3729 0.038 Uiso calc R 1 . .
C C29 0.5695(4) 0.70616(19) 0.44418(14) 0.0263(5) Uani d . 1 . .
H H29 0.6558 0.7157 0.4844 0.032 Uiso calc R 1 . .
C C210 0.4226(3) 0.63695(17) 0.45338(13) 0.0204(5) Uani d . 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
C9a N1 O14 . . 107.33(18) ?
C9a N1 C2 . . 111.83(18) ?
O14 N1 C2 . . 101.68(17) ?
N1 C2 C21 . . 111.32(19) ?
N1 C2 C3 . . 103.50(19) ?
C21 C2 C3 . . 112.36(18) ?
N1 C2 H2 . . 109.8 ?
C21 C2 H2 . . 109.8 ?
C3 C2 H2 . . 109.8 ?
C4 C3 C2 . . 103.0(2) ?
C4 C3 H3A . . 111.2 ?
C2 C3 H3A . . 111.2 ?
C4 C3 H3B . . 111.2 ?
C2 C3 H3B . . 111.2 ?
H3A C3 H3B . . 109.1 ?
O14 C4 C5 . . 105.9(2) ?
O14 C4 C3 . . 104.6(2) ?
C5 C4 C3 . . 114.1(2) ?
O14 C4 H4 . . 110.6 ?
C5 C4 H4 . . 110.6 ?
C3 C4 H4 . . 110.6 ?
C5a C5 C4 . . 108.6(2) ?
C5a C5 H5A . . 110.0 ?
C4 C5 H5A . . 110.0 ?
C5a C5 H5B . . 110.0 ?
C4 C5 H5B . . 110.0 ?
H5A C5 H5B . . 108.4 ?
C6 C5a C9a . . 118.7(2) ?
C6 C5a C5 . . 121.1(2) ?
C9a C5a C5 . . 120.2(2) ?
C7 C6 C5a . . 119.3(2) ?
C7 C6 H6 . . 120.4 ?
C5a C6 H6 . . 120.4 ?
C6 C7 C8 . . 122.6(2) ?
C6 C7 O7 . . 118.6(2) ?
C8 C7 O7 . . 118.7(2) ?
C71 O7 C7 . . 115.70(17) ?
F71 C71 F72 . . 107.8(2) ?
F71 C71 F73 . . 108.1(2) ?
F72 C71 F73 . . 106.3(2) ?
F71 C71 O7 . . 108.03(19) ?
F72 C71 O7 . . 113.5(2) ?
F73 C71 O7 . . 112.9(2) ?
C9 C8 C7 . . 118.0(2) ?
C9 C8 H8 . . 121.0 ?
C7 C8 H8 . . 121.0 ?
C8 C9 C9a . . 120.5(2) ?
C8 C9 H9 . . 119.8 ?
C9a C9 H9 . . 119.8 ?
C9 C9a C5a . . 120.8(2) ?
C9 C9a N1 . . 118.1(2) ?
C5a C9a N1 . . 121.1(2) ?
N1 O14 C4 . . 103.59(18) ?
C22 C21 C210 . . 119.4(2) ?
C22 C21 C2 . . 121.1(2) ?
C210 C21 C2 . . 119.5(2) ?
C21 C22 C23 . . 121.4(2) ?
C21 C22 H22 . . 119.3 ?
C23 C22 H22 . . 119.3 ?
C24 C23 C22 . . 120.6(2) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C23 C24 C25 . . 120.3(2) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C24 C25 C26 . . 121.1(2) ?
C24 C25 C210 . . 120.1(2) ?
C26 C25 C210 . . 118.8(2) ?
C27 C26 C25 . . 121.0(2) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C28 . . 120.2(2) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C29 C28 C27 . . 120.7(3) ?
C29 C28 H28 . . 119.6 ?
C27 C28 H28 . . 119.6 ?
C28 C29 C210 . . 120.7(2) ?
C28 C29 H29 . . 119.7 ?
C210 C29 H29 . . 119.7 ?
C29 C210 C25 . . 118.6(2) ?
C29 C210 C21 . . 123.1(2) ?
C25 C210 C21 . . 118.3(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
N1 C9a . 1.439(3) ?
N1 O14 . 1.439(3) ?
N1 C2 . 1.469(3) ?
C2 C21 . 1.509(3) ?
C2 C3 . 1.545(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.519(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 O14 . 1.447(3) ?
C4 C5 . 1.513(4) ?
C4 H4 . 1.0000 ?
C5 C5a . 1.505(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5a C6 . 1.383(3) ?
C5a C9a . 1.386(3) ?
C6 C7 . 1.366(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.376(4) ?
C7 O7 . 1.416(3) ?
O7 C71 . 1.332(3) ?
C71 F71 . 1.312(3) ?
C71 F72 . 1.321(3) ?
C71 F73 . 1.322(3) ?
C8 C9 . 1.373(3) ?
C8 H8 . 0.9500 ?
C9 C9a . 1.379(3) ?
C9 H9 . 0.9500 ?
C21 C22 . 1.363(3) ?
C21 C210 . 1.431(3) ?
C22 C23 . 1.402(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.355(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.399(4) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.415(4) ?
C25 C210 . 1.419(3) ?
C26 C27 . 1.352(4) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.398(4) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.364(4) ?
C28 H28 . 0.9500 ?
C29 C210 . 1.407(3) ?
C29 H29 . 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
C24 H24 Cg5 2_564 0.95 2.74 3.539(3) 143 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
C9a N1 C2 C21 . . . . -164.99(19) ?
O14 N1 C2 C21 . . . . 80.8(2) ?
C9a N1 C2 C3 . . . . 74.1(2) ?
O14 N1 C2 C3 . . . . -40.1(2) ?
N1 C2 C3 C4 . . . . 16.6(2) ?
C21 C2 C3 C4 . . . . -103.7(2) ?
C2 C3 C4 O14 . . . . 12.9(2) ?
C2 C3 C4 C5 . . . . -102.4(3) ?
O14 C4 C5 C5a . . . . -47.8(3) ?
C3 C4 C5 C5a . . . . 66.7(3) ?
C4 C5 C5a C6 . . . . -173.5(3) ?
C4 C5 C5a C9a . . . . 5.8(3) ?
C9a C5a C6 C7 . . . . -4.5(4) ?
C5 C5a C6 C7 . . . . 174.8(2) ?
C5a C6 C7 C8 . . . . 1.3(4) ?
C5a C6 C7 O7 . . . . 177.3(2) ?
C6 C7 O7 C71 . . . . 90.0(3) ?
C8 C7 O7 C71 . . . . -93.8(3) ?
C7 O7 C71 F71 . . . . 178.7(2) ?
C7 O7 C71 F72 . . . . -61.8(3) ?
C7 O7 C71 F73 . . . . 59.2(3) ?
C6 C7 C8 C9 . . . . 2.0(4) ?
O7 C7 C8 C9 . . . . -174.1(2) ?
C7 C8 C9 C9a . . . . -1.9(3) ?
C8 C9 C9a C5a . . . . -1.4(4) ?
C8 C9 C9a N1 . . . . 177.7(2) ?
C6 C5a C9a C9 . . . . 4.6(4) ?
C5 C5a C9a C9 . . . . -174.7(2) ?
C6 C5a C9a N1 . . . . -174.5(2) ?
C5 C5a C9a N1 . . . . 6.1(3) ?
O14 N1 C9a C9 . . . . -154.4(2) ?
C2 N1 C9a C9 . . . . 94.9(3) ?
O14 N1 C9a C5a . . . . 24.8(3) ?
C2 N1 C9a C5a . . . . -85.9(3) ?
C9a N1 O14 C4 . . . . -67.8(2) ?
C2 N1 O14 C4 . . . . 49.7(2) ?
C5 C4 O14 N1 . . . . 82.2(2) ?
C3 C4 O14 N1 . . . . -38.7(2) ?
N1 C2 C21 C22 . . . . -10.7(3) ?
C3 C2 C21 C22 . . . . 104.9(3) ?
N1 C2 C21 C210 . . . . 170.98(19) ?
C3 C2 C21 C210 . . . . -73.4(3) ?
C210 C21 C22 C23 . . . . 0.3(3) ?
C2 C21 C22 C23 . . . . -178.0(2) ?
C21 C22 C23 C24 . . . . -0.6(4) ?
C22 C23 C24 C25 . . . . 0.4(4) ?
C23 C24 C25 C26 . . . . 179.3(2) ?
C23 C24 C25 C210 . . . . 0.0(4) ?
C24 C25 C26 C27 . . . . -179.6(2) ?
C210 C25 C26 C27 . . . . -0.3(4) ?
C25 C26 C27 C28 . . . . -0.1(4) ?
C26 C27 C28 C29 . . . . 0.4(4) ?
C27 C28 C29 C210 . . . . -0.1(4) ?
C28 C29 C210 C25 . . . . -0.3(3) ?
C28 C29 C210 C21 . . . . 179.7(2) ?
C24 C25 C210 C29 . . . . 179.8(2) ?
C26 C25 C210 C29 . . . . 0.5(3) ?
C24 C25 C210 C21 . . . . -0.2(3) ?
C26 C25 C210 C21 . . . . -179.5(2) ?
C22 C21 C210 C29 . . . . -180.0(2) ?
C2 C21 C210 C29 . . . . -1.7(3) ?
C22 C21 C210 C25 . . . . 0.1(3) ?
C2 C21 C210 C25 . . . . 178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654263
