#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/80/2218081.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_2218081
loop_
_publ_author_name
'Cheng, Xiang-Wei'
_publ_section_title
;
 3-(3-Chloropropyl)-7,8-dimethoxy-1H-3-benzazepin-2(3H)-one
 at 125K
;
_journal_coeditor_code           CI2582
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o906
_journal_paper_doi               10.1107/S1600536808011264
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H18 Cl N O3'
_chemical_formula_moiety         'C15 H18 Cl N O3'
_chemical_formula_sum            'C15 H18 Cl N O3'
_chemical_formula_weight         295.75
_chemical_name_systematic
;
3-(3-Chloropropyl)-7,8-dimethoxy-1H-3-benzazepin-2(3H)-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.667(6)
_cell_angle_beta                 114.701(6)
_cell_angle_gamma                94.460(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3141(17)
_cell_length_b                   9.5924(17)
_cell_length_c                   9.6359(17)
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.2
_cell_volume                     744.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7023
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.9277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0542P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                2092
_reflns_number_total             2574
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2582.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               2218081
_cod_database_fobs_code          2218081
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
Cl Cl1 0.40282(11) -0.14655(9) 0.18804(11) 0.1048(3) Uani d . 1
O O1 -0.20936(16) 0.23306(15) 0.46481(17) 0.0598(4) Uani d . 1
O O2 -0.31187(14) 0.39739(15) 0.28346(16) 0.0535(3) Uani d . 1
O O3 0.15852(19) 0.32805(18) -0.03080(19) 0.0722(4) Uani d . 1
N N1 0.31547(18) 0.24927(17) 0.17583(19) 0.0513(4) Uani d . 1
C C2 -0.16173(19) 0.37032(18) 0.3119(2) 0.0422(4) Uani d . 1
C C4 0.0877(2) 0.39343(19) 0.2909(2) 0.0445(4) Uani d . 1
C C6 0.0472(2) 0.2518(2) 0.4511(2) 0.0476(4) Uani d . 1
H H6 0.0858 0.1949 0.5196 0.057 Uiso calc R 1
C C1 -0.1044(2) 0.28198(19) 0.4125(2) 0.0447(4) Uani d . 1
C C10 0.1945(2) 0.4592(2) 0.2308(3) 0.0557(5) Uani d . 1
H H10A 0.2980 0.5093 0.3203 0.067 Uiso calc R 1
H H10B 0.1452 0.5306 0.1797 0.067 Uiso calc R 1
C C3 -0.0662(2) 0.42458(19) 0.2514(2) 0.0450(4) Uani d . 1
H H3 -0.1046 0.4823 0.1839 0.054 Uiso calc R 1
C C5 0.1450(2) 0.30533(19) 0.3888(2) 0.0455(4) Uani d . 1
C C7 0.3048(2) 0.2705(2) 0.4297(2) 0.0536(5) Uani d . 1
H H7 0.3613 0.2625 0.5321 0.064 Uiso calc R 1
C C9 0.2193(2) 0.3412(2) 0.1127(3) 0.0540(5) Uani d . 1
C C8 0.3789(2) 0.2489(2) 0.3359(2) 0.0556(5) Uani d . 1
H H8 0.4831 0.2318 0.3815 0.067 Uiso calc R 1
C C11 0.3610(2) 0.1450(2) 0.0693(3) 0.0623(6) Uani d . 1
H H11A 0.4657 0.1257 0.1324 0.075 Uiso calc R 1
H H11B 0.3707 0.1894 -0.0078 0.075 Uiso calc R 1
C C15 -0.3741(2) 0.4838(2) 0.1797(3) 0.0607(5) Uani d . 1
H H15A -0.4794 0.4958 0.1684 0.091 Uiso calc R 1
H H15B -0.3814 0.4361 0.0768 0.091 Uiso calc R 1
H H15C -0.3037 0.5780 0.2234 0.091 Uiso calc R 1
C C14 -0.1591(3) 0.1435(3) 0.5654(4) 0.0892(8) Uani d . 1
H H14A -0.2426 0.1169 0.5934 0.134 Uiso calc R 1
H H14B -0.0630 0.1957 0.6607 0.134 Uiso calc R 1
H H14C -0.1373 0.0566 0.5107 0.134 Uiso calc R 1
C C12 0.2402(3) 0.0012(3) -0.0196(3) 0.0729(7) Uani d . 1
H H12A 0.1358 0.0215 -0.0819 0.088 Uiso calc R 1
H H12B 0.2723 -0.0581 -0.0940 0.088 Uiso calc R 1
C C13 0.2220(3) -0.0865(3) 0.0846(3) 0.0822(7) Uani d . 1
H H13A 0.1351 -0.1710 0.0188 0.099 Uiso calc R 1
H H13B 0.1932 -0.0270 0.1618 0.099 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'
Cl Cl 0.1484 0.1585 '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
C1 O1 C14 117.58(15)
C2 O2 C15 116.59(14)
C9 N1 C8 125.16(16)
C9 N1 C11 117.85(17)
C8 N1 C11 116.96(16)
O2 C2 C3 124.88(16)
O2 C2 C1 115.42(15)
C3 C2 C1 119.69(15)
C5 C4 C3 120.30(16)
C5 C4 C10 119.48(15)
C3 C4 C10 120.20(16)
C1 C6 C5 121.25(17)
C1 C6 H6 119.4
C5 C6 H6 119.4
O1 C1 C6 125.56(16)
O1 C1 C2 114.89(15)
C6 C1 C2 119.54(16)
C4 C10 C9 110.38(15)
C4 C10 H10A 109.6
C9 C10 H10A 109.6
C4 C10 H10B 109.6
C9 C10 H10B 109.6
H10A C10 H10B 108.1
C2 C3 C4 120.54(16)
C2 C3 H3 119.7
C4 C3 H3 119.7
C4 C5 C6 118.65(15)
C4 C5 C7 120.94(17)
C6 C5 C7 120.40(17)
C8 C7 C5 127.12(18)
C8 C7 H7 116.4
C5 C7 H7 116.4
O3 C9 N1 121.47(18)
O3 C9 C10 122.68(19)
N1 C9 C10 115.85(18)
C7 C8 N1 126.72(17)
C7 C8 H8 116.6
N1 C8 H8 116.6
N1 C11 C12 112.93(16)
N1 C11 H11A 109.0
C12 C11 H11A 109.0
N1 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
O2 C15 H15A 109.5
O2 C15 H15B 109.5
H15A C15 H15B 109.5
O2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C12 C11 115.1(2)
C13 C12 H12A 108.5
C11 C12 H12A 108.5
C13 C12 H12B 108.5
C11 C12 H12B 108.5
H12A C12 H12B 107.5
C12 C13 Cl1 111.93(17)
C12 C13 H13A 109.2
Cl1 C13 H13A 109.2
C12 C13 H13B 109.2
Cl1 C13 H13B 109.2
H13A C13 H13B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.783(3)
O1 C1 1.372(2)
O1 C14 1.405(3)
O2 C2 1.367(2)
O2 C15 1.416(2)
O3 C9 1.225(2)
N1 C9 1.368(3)
N1 C8 1.404(3)
N1 C11 1.476(2)
C2 C3 1.381(2)
C2 C1 1.403(2)
C4 C5 1.384(3)
C4 C3 1.398(2)
C4 C10 1.510(3)
C6 C1 1.375(2)
C6 C5 1.409(3)
C6 H6 0.93
C10 C9 1.510(3)
C10 H10A 0.97
C10 H10B 0.97
C3 H3 0.93
C5 C7 1.460(2)
C7 C8 1.338(3)
C7 H7 0.93
C8 H8 0.93
C11 C12 1.515(3)
C11 H11A 0.97
C11 H11B 0.97
C15 H15A 0.96
C15 H15B 0.96
C15 H15C 0.96
C14 H14A 0.96
C14 H14B 0.96
C14 H14C 0.96
C12 C13 1.504(4)
C12 H12A 0.97
C12 H12B 0.97
C13 H13A 0.97
C13 H13B 0.97
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
C3 H3 O3 2_565 0.93 2.56 3.473(2) 169 yes
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
C15 O2 C2 C3 2.2(3)
C15 O2 C2 C1 -178.74(16)
C14 O1 C1 C6 -0.5(3)
C14 O1 C1 C2 179.7(2)
C5 C6 C1 O1 178.90(16)
C5 C6 C1 C2 -1.3(3)
O2 C2 C1 O1 1.4(2)
C3 C2 C1 O1 -179.52(15)
O2 C2 C1 C6 -178.43(15)
C3 C2 C1 C6 0.7(3)
C5 C4 C10 C9 68.9(2)
C3 C4 C10 C9 -112.88(19)
O2 C2 C3 C4 178.40(16)
C1 C2 C3 C4 -0.6(3)
C5 C4 C3 C2 1.2(3)
C10 C4 C3 C2 -176.99(16)
C3 C4 C5 C6 -1.8(3)
C10 C4 C5 C6 176.41(16)
C3 C4 C5 C7 179.33(16)
C10 C4 C5 C7 -2.4(3)
C1 C6 C5 C4 1.9(3)
C1 C6 C5 C7 -179.24(17)
C4 C5 C7 C8 -35.3(3)
C6 C5 C7 C8 145.9(2)
C8 N1 C9 O3 -174.47(18)
C11 N1 C9 O3 7.6(3)
C8 N1 C9 C10 5.9(3)
C11 N1 C9 C10 -172.03(16)
C4 C10 C9 O3 109.0(2)
C4 C10 C9 N1 -71.4(2)
C5 C7 C8 N1 -2.8(4)
C9 N1 C8 C7 37.8(3)
C11 N1 C8 C7 -144.2(2)
C9 N1 C11 C12 -88.5(2)
C8 N1 C11 C12 93.4(2)
N1 C11 C12 C13 -63.4(3)
C11 C12 C13 Cl1 -64.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14331761
