#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017280.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_2017280
loop_
_publ_author_name
'Gómez, Sandra L.'
'Sanabria, Carlos M.'
'Palma, Alirio'
'Bahsas, Ali'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Four differently substituted
 2-aryl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepines:
 hydrogen-bonded structures in one, two and three dimensions
;
_journal_coeditor_code           FA3200
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o465
_journal_page_last               o469
_journal_paper_doi               10.1107/S0108270109030339
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H19 N O'
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_name_systematic
;
(2SR,4RS)-7-methyl-2-exo-(4-methylphenyl)-
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                 108.222(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7687(9)
_cell_length_b                   10.3022(17)
_cell_length_c                   14.239(2)
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.95
_cell_volume                     1361.1(3)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Hooft, 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'
_diffrn_measurement_method       'φ & 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  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20555
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0626
_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)+(0.0346P)²+1.1025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                1788
_reflns_number_total             3133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3200.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017280
_cod_database_fobs_code          2017280
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
N N1 0.5776(2) 0.74452(19) 0.11344(14) 0.0240(5) Uani d . 1 . .
C C2 0.4350(2) 0.8051(2) 0.06260(17) 0.0234(5) Uani d . 1 . .
H H2 0.4391 0.8989 0.0814 0.028 Uiso calc R 1 . .
C C3 0.4205(2) 0.7951(3) -0.04817(17) 0.0271(6) Uani d . 1 . .
H H3A 0.3288 0.7525 -0.0856 0.033 Uiso calc R 1 . .
H H3B 0.4245 0.8821 -0.0768 0.033 Uiso calc R 1 . .
C C4 0.5488(3) 0.7131(2) -0.04985(18) 0.0270(6) Uani d . 1 . .
H H4 0.5204 0.6497 -0.1058 0.032 Uiso calc R 1 . .
C C5 0.6774(3) 0.7917(3) -0.05328(18) 0.0279(6) Uani d . 1 . .
H H5A 0.7522 0.7331 -0.0629 0.033 Uiso calc R 1 . .
H H5B 0.6483 0.8527 -0.1097 0.033 Uiso calc R 1 . .
C C5a 0.7380(2) 0.8664(2) 0.04163(17) 0.0229(5) Uani d . 1 . .
C C6 0.8399(2) 0.9631(2) 0.05250(18) 0.0247(5) Uani d . 1 . .
H H6 0.8738 0.9828 -0.0015 0.030 Uiso calc R 1 . .
C C7 0.8940(2) 1.0321(2) 0.13958(18) 0.0244(5) Uani d . 1 . .
C C8 0.8469(2) 0.9994(2) 0.21876(18) 0.0266(6) Uani d . 1 . .
H H8 0.8841 1.0443 0.2798 0.032 Uiso calc R 1 . .
C C9 0.7467(2) 0.9025(2) 0.20966(17) 0.0253(6) Uani d . 1 . .
H H9 0.7158 0.8801 0.2645 0.030 Uiso calc R 1 . .
C C9a 0.6909(2) 0.8376(2) 0.12113(17) 0.0219(5) Uani d . 1 . .
O O14 0.58803(17) 0.64596(16) 0.04384(12) 0.0272(4) Uani d . 1 . .
C C21 0.3162(2) 0.7410(2) 0.09166(17) 0.0234(5) Uani d . 1 . .
C C22 0.2453(3) 0.8088(2) 0.14585(17) 0.0266(6) Uani d . 1 . .
H H22 0.2732 0.8957 0.1651 0.032 Uiso calc R 1 . .
C C23 0.1343(2) 0.7532(3) 0.17280(18) 0.0292(6) Uani d . 1 . .
H H23 0.0865 0.8024 0.2096 0.035 Uiso calc R 1 . .
C C24 0.0923(3) 0.6271(3) 0.14689(19) 0.0292(6) Uani d . 1 . .
C C25 0.1652(3) 0.5583(3) 0.0938(2) 0.0329(6) Uani d . 1 . .
H H25 0.1391 0.4707 0.0762 0.040 Uiso calc R 1 . .
C C26 0.2748(3) 0.6139(2) 0.0658(2) 0.0303(6) Uani d . 1 . .
H H26 0.3221 0.5649 0.0285 0.036 Uiso calc R 1 . .
C C27 -0.0301(3) 0.5662(3) 0.1741(2) 0.0386(7) Uani d . 1 . .
H H27A -0.0443 0.6129 0.2304 0.058 Uiso calc R 1 . .
H H27B -0.0073 0.4752 0.1922 0.058 Uiso calc R 1 . .
H H27C -0.1184 0.5710 0.1176 0.058 Uiso calc R 1 . .
C C71 0.9999(3) 1.1401(3) 0.1486(2) 0.0340(6) Uani d . 1 . .
H H71A 1.0981 1.1060 0.1752 0.051 Uiso calc R 1 . .
H H71B 0.9843 1.2069 0.1931 0.051 Uiso calc R 1 . .
H H71C 0.9867 1.1781 0.0832 0.051 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
C9a N1 O14 . . 107.61(16) ?
C9a N1 C2 . . 109.68(18) ?
O14 N1 C2 . . 102.51(16) ?
N1 C2 C21 . . 111.55(19) ?
N1 C2 C3 . . 103.98(18) ?
C21 C2 C3 . . 114.9(2) ?
N1 C2 H2 . . 108.7 ?
C21 C2 H2 . . 108.7 ?
C3 C2 H2 . . 108.7 ?
C4 C3 C2 . . 103.95(19) ?
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 . . 107.7(2) ?
O14 C4 C3 . . 103.53(18) ?
C5 C4 C3 . . 113.7(2) ?
O14 C4 H4 . . 110.5 ?
C5 C4 H4 . . 110.5 ?
C3 C4 H4 . . 110.5 ?
C5a C5 C4 . . 110.1(2) ?
C5a C5 H5A . . 109.6 ?
C4 C5 H5A . . 109.6 ?
C5a C5 H5B . . 109.6 ?
C4 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.2 ?
C9a C5a C6 . . 118.4(2) ?
C9a C5a C5 . . 119.2(2) ?
C6 C5a C5 . . 122.4(2) ?
C5a C6 C7 . . 122.1(2) ?
C5a C6 H6 . . 119.0 ?
C7 C6 H6 . . 119.0 ?
C6 C7 C8 . . 118.3(2) ?
C6 C7 C71 . . 121.2(2) ?
C8 C7 C71 . . 120.5(2) ?
C9 C8 C7 . . 120.5(2) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C9a . . 120.3(2) ?
C8 C9 H9 . . 119.9 ?
C9a C9 H9 . . 119.9 ?
C9 C9a C5a . . 120.5(2) ?
C9 C9a N1 . . 117.8(2) ?
C5a C9a N1 . . 121.7(2) ?
C4 O14 N1 . . 103.99(16) ?
C22 C21 C26 . . 118.2(2) ?
C22 C21 C2 . . 119.9(2) ?
C26 C21 C2 . . 121.9(2) ?
C21 C22 C23 . . 121.3(2) ?
C21 C22 H22 . . 119.3 ?
C23 C22 H22 . . 119.3 ?
C24 C23 C22 . . 120.7(2) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C23 C24 C25 . . 117.9(2) ?
C23 C24 C27 . . 121.2(2) ?
C25 C24 C27 . . 120.9(2) ?
C26 C25 C24 . . 121.6(2) ?
C26 C25 H25 . . 119.2 ?
C24 C25 H25 . . 119.2 ?
C25 C26 C21 . . 120.3(2) ?
C25 C26 H26 . . 119.9 ?
C21 C26 H26 . . 119.9 ?
C24 C27 H27A . . 109.5 ?
C24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C7 C71 H71A . . 109.5 ?
C7 C71 H71B . . 109.5 ?
H71A C71 H71B . . 109.5 ?
C7 C71 H71C . . 109.5 ?
H71A C71 H71C . . 109.5 ?
H71B C71 H71C . . 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
N1 C9a . 1.442(3) ?
N1 O14 . 1.444(2) ?
N1 C2 . 1.492(3) ?
C2 C21 . 1.502(3) ?
C2 C3 . 1.542(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.518(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 O14 . 1.444(3) ?
C4 C5 . 1.508(3) ?
C4 H4 . 1.0000 ?
C5 C5a . 1.506(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5a C9a . 1.381(3) ?
C5a C6 . 1.382(3) ?
C6 C7 . 1.383(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.386(3) ?
C7 C71 . 1.497(3) ?
C8 C9 . 1.376(3) ?
C8 H8 . 0.9500 ?
C9 C9a . 1.380(3) ?
C9 H9 . 0.9500 ?
C21 C22 . 1.378(3) ?
C21 C26 . 1.386(3) ?
C22 C23 . 1.382(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.377(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.386(4) ?
C24 C27 . 1.504(3) ?
C25 C26 . 1.378(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
C71 H71A . 0.9800 ?
C71 H71B . 0.9800 ?
C71 H71C . 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
C8 H8 N1 2_655 0.95 2.52 3.395(3) 153 no
C3 H3B Cg1 3_675 0.99 2.77 3.465(3) 127 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 . . . . -154.23(19) ?
O14 N1 C2 C21 . . . . 91.7(2) ?
C9a N1 C2 C3 . . . . 81.4(2) ?
O14 N1 C2 C3 . . . . -32.7(2) ?
N1 C2 C3 C4 . . . . 7.3(2) ?
C21 C2 C3 C4 . . . . -114.9(2) ?
C2 C3 C4 O14 . . . . 20.8(2) ?
C2 C3 C4 C5 . . . . -95.8(2) ?
O14 C4 C5 C5a . . . . -47.5(3) ?
C3 C4 C5 C5a . . . . 66.6(3) ?
C4 C5 C5a C9a . . . . 11.6(3) ?
C4 C5 C5a C6 . . . . -168.6(2) ?
C9a C5a C6 C7 . . . . -0.8(3) ?
C5 C5a C6 C7 . . . . 179.4(2) ?
C5a C6 C7 C8 . . . . 2.0(3) ?
C5a C6 C7 C71 . . . . -177.5(2) ?
C6 C7 C8 C9 . . . . -1.3(3) ?
C71 C7 C8 C9 . . . . 178.3(2) ?
C7 C8 C9 C9a . . . . -0.6(4) ?
C8 C9 C9a C5a . . . . 1.9(4) ?
C8 C9 C9a N1 . . . . -175.0(2) ?
C6 C5a C9a C9 . . . . -1.2(3) ?
C5 C5a C9a C9 . . . . 178.6(2) ?
C6 C5a C9a N1 . . . . 175.6(2) ?
C5 C5a C9a N1 . . . . -4.6(3) ?
O14 N1 C9a C9 . . . . -150.51(19) ?
C2 N1 C9a C9 . . . . 98.7(2) ?
O14 N1 C9a C5a . . . . 32.6(3) ?
C2 N1 C9a C5a . . . . -78.2(3) ?
C5 C4 O14 N1 . . . . 78.1(2) ?
C3 C4 O14 N1 . . . . -42.6(2) ?
C9a N1 O14 C4 . . . . -68.0(2) ?
C2 N1 O14 C4 . . . . 47.6(2) ?
N1 C2 C21 C22 . . . . 113.0(2) ?
C3 C2 C21 C22 . . . . -129.0(2) ?
N1 C2 C21 C26 . . . . -66.9(3) ?
C3 C2 C21 C26 . . . . 51.1(3) ?
C26 C21 C22 C23 . . . . -0.9(4) ?
C2 C21 C22 C23 . . . . 179.2(2) ?
C21 C22 C23 C24 . . . . 0.6(4) ?
C22 C23 C24 C25 . . . . 0.4(4) ?
C22 C23 C24 C27 . . . . -178.8(2) ?
C23 C24 C25 C26 . . . . -1.1(4) ?
C27 C24 C25 C26 . . . . 178.1(2) ?
C24 C25 C26 C21 . . . . 0.9(4) ?
C22 C21 C26 C25 . . . . 0.1(4) ?
C2 C21 C26 C25 . . . . -180.0(2) ?
