#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017636.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_2017636
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_moiety         'C15 H18 Cl N O'
_chemical_formula_sum            'C15 H18 Cl N O'
_chemical_formula_weight         263.75
_chemical_name_systematic
;
(2RS,4RS)-8-chloro-9-methyl-2-endo-(2-methylprop-1-enyl)-
2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.554(15)
_cell_angle_beta                 94.684(15)
_cell_angle_gamma                97.298(14)
_cell_formula_units_Z            2
_cell_length_a                   5.2890(9)
_cell_length_b                   9.3076(16)
_cell_length_c                   13.551(3)
_cell_measurement_reflns_used    3005
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.79
_cell_volume                     656.7(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16228
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.358
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0491
_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)+(0.0380P)²+0.5092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2348
_reflns_number_total             3005
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3373.cif
_cod_data_source_block           IV
_cod_database_code               2017636
_cod_database_fobs_code          2017636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl8 0.73078(12) 0.74226(5) 0.21073(4) 0.03620(17) Uani d . 1 . .
O O14 0.6146(2) 0.07431(14) 0.12657(10) 0.0230(3) Uani d . 1 . .
N N1 0.6629(3) 0.18689(17) 0.20756(12) 0.0191(3) Uani d . 1 . .
C C2 0.5250(4) 0.1133(2) 0.28500(15) 0.0242(4) Uani d . 1 . .
H H2 0.6309 0.0404 0.3110 0.029 Uiso calc R 1 . .
C C3 0.2807(4) 0.0301(2) 0.22771(15) 0.0254(4) Uani d . 1 . .
H H3A 0.2483 -0.0706 0.2470 0.031 Uiso calc R 1 . .
H H3B 0.1300 0.0800 0.2395 0.031 Uiso calc R 1 . .
C C4 0.3402(4) 0.0311(2) 0.12007(15) 0.0234(4) Uani d . 1 . .
H H4 0.2926 -0.0678 0.0840 0.028 Uiso calc R 1 . .
C C5 0.2183(4) 0.1429(2) 0.06578(15) 0.0228(4) Uani d . 1 . .
H H5A 0.2398 0.1281 -0.0061 0.027 Uiso calc R 1 . .
H H5B 0.0327 0.1321 0.0739 0.027 Uiso calc R 1 . .
C C5a 0.3407(4) 0.2930(2) 0.10635(14) 0.0191(4) Uani d . 1 . .
C C6 0.2486(4) 0.4150(2) 0.07421(16) 0.0274(5) Uani d . 1 . .
H H6 0.1016 0.4040 0.0277 0.033 Uiso calc R 1 . .
C C7 0.3654(4) 0.5516(2) 0.10817(16) 0.0297(5) Uani d . 1 . .
H H7 0.3005 0.6349 0.0855 0.036 Uiso calc R 1 . .
C C8 0.5780(4) 0.5666(2) 0.17553(15) 0.0246(4) Uani d . 1 . .
C C9 0.6787(4) 0.4489(2) 0.21219(14) 0.0194(4) Uani d . 1 . .
C C9a 0.5537(3) 0.31158(19) 0.17540(13) 0.0169(4) Uani d . 1 . .
C C21 0.4772(4) 0.2126(2) 0.37011(15) 0.0260(4) Uani d . 1 . .
H H21 0.3520 0.2755 0.3584 0.031 Uiso calc R 1 . .
C C22 0.5935(4) 0.2218(2) 0.46155(16) 0.0297(5) Uani d . 1 . .
C C23 0.8029(5) 0.1396(3) 0.4932(2) 0.0474(7) Uani d . 1 . .
H H23A 0.8582 0.0874 0.4348 0.071 Uiso calc R 1 . .
H H23B 0.7418 0.0697 0.5392 0.071 Uiso calc R 1 . .
H H23C 0.9474 0.2071 0.5266 0.071 Uiso calc R 1 . .
C C24 0.5118(5) 0.3198(3) 0.54187(18) 0.0465(7) Uani d . 1 . .
H H24A 0.3681 0.3665 0.5152 0.070 Uiso calc R 1 . .
H H24B 0.6551 0.3945 0.5670 0.070 Uiso calc R 1 . .
H H24C 0.4583 0.2629 0.5962 0.070 Uiso calc R 1 . .
C C91 0.9103(4) 0.4665(2) 0.28569(15) 0.0255(4) Uani d . 1 . .
H H91A 1.0328 0.5479 0.2703 0.038 Uiso calc R 1 . .
H H91B 0.9901 0.3770 0.2820 0.038 Uiso calc R 1 . .
H H91C 0.8595 0.4860 0.3529 0.038 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'
Cl Cl 0.1484 0.1585 '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 . . 104.10(13) ?
O14 N1 C9a . . 107.54(14) ?
O14 N1 C2 . . 100.29(14) ?
C9a N1 C2 . . 113.92(15) ?
C21 C2 N1 . . 114.18(16) ?
C21 C2 C3 . . 114.01(17) ?
N1 C2 C3 . . 104.22(16) ?
C21 C2 H2 . . 108.0 ?
N1 C2 H2 . . 108.0 ?
C3 C2 H2 . . 108.0 ?
C4 C3 C2 . . 103.08(16) ?
C4 C3 H3A . . 111.1 ?
C2 C3 H3A . . 111.1 ?
C4 C3 H3B . . 111.1 ?
C2 C3 H3B . . 111.1 ?
H3A C3 H3B . . 109.1 ?
O14 C4 C5 . . 106.92(15) ?
O14 C4 C3 . . 103.98(15) ?
C5 C4 C3 . . 113.35(16) ?
O14 C4 H4 . . 110.8 ?
C5 C4 H4 . . 110.8 ?
C3 C4 H4 . . 110.8 ?
C4 C5 C5a . . 109.79(16) ?
C4 C5 H5B . . 109.7 ?
C5a C5 H5B . . 109.7 ?
C4 C5 H5A . . 109.7 ?
C5a C5 H5A . . 109.7 ?
H5B C5 H5A . . 108.2 ?
C6 C5a C9a . . 118.50(18) ?
C6 C5a C5 . . 121.01(18) ?
C9a C5a C5 . . 120.47(17) ?
C7 C6 C5a . . 121.11(19) ?
C7 C6 H6 . . 119.4 ?
C5a C6 H6 . . 119.4 ?
C6 C7 C8 . . 119.13(19) ?
C6 C7 H7 . . 120.4 ?
C8 C7 H7 . . 120.4 ?
C7 C8 C9 . . 122.85(18) ?
C7 C8 Cl8 . . 117.31(16) ?
C9 C8 Cl8 . . 119.78(16) ?
C8 C9 C9a . . 116.06(18) ?
C8 C9 C91 . . 122.44(17) ?
C9a C9 C91 . . 121.50(17) ?
C5a C9a C9 . . 122.34(17) ?
C5a C9a N1 . . 120.22(16) ?
C9 C9a N1 . . 117.35(16) ?
C22 C21 C2 . . 125.9(2) ?
C22 C21 H21 . . 117.1 ?
C2 C21 H21 . . 117.0 ?
C21 C22 C23 . . 125.2(2) ?
C21 C22 C24 . . 119.9(2) ?
C23 C22 C24 . . 114.9(2) ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C22 C24 H24A . . 109.5 ?
C22 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C22 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C9 C91 H91A . . 109.5 ?
C9 C91 H91B . . 109.5 ?
H91A C91 H91B . . 109.5 ?
C9 C91 H91C . . 109.5 ?
H91A C91 H91C . . 109.5 ?
H91B C91 H91C . . 109.5 ?
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
Cl8 C8 . 1.741(2) ?
O14 N1 . 1.4392(19) ?
O14 C4 . 1.450(2) ?
N1 C9a . 1.442(2) ?
N1 C2 . 1.488(3) ?
C2 C21 . 1.479(3) ?
C2 C3 . 1.536(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.518(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.501(3) ?
C4 H4 . 1.0000 ?
C5 C5a . 1.505(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5a C6 . 1.378(3) ?
C5a C9a . 1.388(3) ?
C6 C7 . 1.368(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.375(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.387(3) ?
C9 C9a . 1.396(2) ?
C9 C91 . 1.497(3) ?
C21 C22 . 1.329(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.479(3) ?
C22 C24 . 1.491(3) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
C91 H91A . 0.9800 ?
C91 H91B . 0.9800 ?
C91 H91C . 0.9800 ?
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 H5B O14 1_455 0.99 2.39 3.358(3) 166 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 . . . . -69.19(17) ?
C4 O14 N1 C2 . . . . 50.12(16) ?
O14 N1 C2 C21 . . . . -164.40(16) ?
C9a N1 C2 C21 . . . . -49.8(2) ?
O14 N1 C2 C3 . . . . -39.38(17) ?
C9a N1 C2 C3 . . . . 75.18(19) ?
C21 C2 C3 C4 . . . . 140.31(17) ?
N1 C2 C3 C4 . . . . 15.18(19) ?
N1 O14 C4 C5 . . . . 79.45(17) ?
N1 O14 C4 C3 . . . . -40.72(17) ?
C2 C3 C4 O14 . . . . 14.57(19) ?
C2 C3 C4 C5 . . . . -101.17(18) ?
O14 C4 C5 C5a . . . . -45.5(2) ?
C3 C4 C5 C5a . . . . 68.5(2) ?
C4 C5 C5a C6 . . . . -174.80(18) ?
C4 C5 C5a C9a . . . . 6.9(2) ?
C9a C5a C6 C7 . . . . 0.9(3) ?
C5 C5a C6 C7 . . . . -177.50(19) ?
C5a C6 C7 C8 . . . . 0.0(3) ?
C6 C7 C8 C9 . . . . -1.0(3) ?
C6 C7 C8 Cl8 . . . . 176.25(17) ?
C7 C8 C9 C9a . . . . 1.0(3) ?
Cl8 C8 C9 C9a . . . . -176.12(14) ?
C7 C8 C9 C91 . . . . -179.91(19) ?
Cl8 C8 C9 C91 . . . . 2.9(3) ?
C6 C5a C9a C9 . . . . -0.8(3) ?
C5 C5a C9a C9 . . . . 177.59(17) ?
C6 C5a C9a N1 . . . . -177.20(17) ?
C5 C5a C9a N1 . . . . 1.2(3) ?
C8 C9 C9a C5a . . . . -0.1(3) ?
C91 C9 C9a C5a . . . . -179.21(17) ?
C8 C9 C9a N1 . . . . 176.37(17) ?
C91 C9 C9a N1 . . . . -2.7(3) ?
O14 N1 C9a C5a . . . . 29.7(2) ?
C2 N1 C9a C5a . . . . -80.5(2) ?
O14 N1 C9a C9 . . . . -146.86(15) ?
C2 N1 C9a C9 . . . . 102.95(19) ?
N1 C2 C21 C22 . . . . -108.4(2) ?
C3 C2 C21 C22 . . . . 132.0(2) ?
C2 C21 C22 C23 . . . . 3.6(4) ?
C2 C21 C22 C24 . . . . -175.6(2) ?
