#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210977.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_2210977
loop_
_publ_author_name
'Zhao-Ling Meng'
'Ai-Ling Sun'
'Ren-Min Liu'
'Da-Qi Wang'
_publ_section_title
;(6R,10R,14E)-6-Amino-12-ethylidene-8-methyl-6,7,10,12-tetrahydro-6,10-methanocycloocta[b]pyridin-2(1H)-one
 monohydrate
;
_journal_coeditor_code           ER2016
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4911
_journal_page_last               o4912
_journal_paper_doi               10.1107/S160053680603981X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H18 N2 O, H2 O'
_chemical_formula_moiety         'C15 H18 N2 O, H2 O'
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_weight         260.33
_chemical_name_systematic
;
(6R,10R,14E)-6-Amino-12-ethylidene-8-methyl-6,7,10,12-tetrahydro-6,10-
methanocycloocta[b]pyridin-2(1H)-one monohydrate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.731(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.00(2)
_cell_length_b                   12.35(2)
_cell_length_c                   8.838(14)
_cell_measurement_reflns_used    682
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.106
_cell_measurement_theta_min      2.275
_cell_volume                     1419(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0791
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3603
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0786P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                751
_reflns_number_total             1292
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2016.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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      'C 2'
_cod_database_code               2210977
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
N N1 0.8847(4) 0.3330(4) 0.8217(5) 0.0421(14) Uani d . 1
H H1 0.9473 0.3537 0.8468 0.051 Uiso calc R 1
N N2 0.6021(4) 0.1441(5) 0.4456(6) 0.0591(18) Uani d . 1
H H2A 0.5822 0.1478 0.5264 0.071 Uiso d R 1
H H2B 0.5527 0.1330 0.3538 0.071 Uiso d R 1
O O1 0.9042(3) 0.3612(4) 1.0844(5) 0.0550(13) Uani d . 1
O O2 0.9567(4) 0.5875(5) 0.1216(7) 0.094(2) Uani d . 1
H H16 0.9401 0.5210 0.1163 0.113 Uiso d R 1
H H17 0.9290 0.6109 0.0246 0.113 Uiso d R 1
C C1 0.8459(4) 0.3315(5) 0.9425(7) 0.0457(18) Uani d . 1
C C2 0.7446(4) 0.2966(6) 0.8981(7) 0.0474(18) Uani d . 1
H H2 0.7143 0.2937 0.9756 0.057 Uiso calc R 1
C C3 0.6898(5) 0.2667(6) 0.7417(7) 0.0523(19) Uani d . 1
H H3 0.6223 0.2433 0.7142 0.063 Uiso calc R 1
C C4 0.7324(5) 0.2700(5) 0.6200(7) 0.0411(16) Uani d . 1
C C5 0.8307(4) 0.3038(5) 0.6632(6) 0.0373(15) Uani d . 1
C C6 0.6691(4) 0.2336(5) 0.4429(7) 0.0417(17) Uani d . 1
C C7 0.6021(5) 0.3287(6) 0.3509(7) 0.0497(18) Uani d . 1
H H7A 0.5489 0.3009 0.2533 0.060 Uiso calc R 1
H H7B 0.5684 0.3599 0.4189 0.060 Uiso calc R 1
C C8 0.6585(6) 0.4162(5) 0.3032(7) 0.0463(17) Uani d . 1
C C9 0.7546(6) 0.4023(5) 0.3150(7) 0.0467(17) Uani d . 1
H H9 0.7870 0.4595 0.2849 0.056 Uiso calc R 1
C C10 0.8144(4) 0.3007(5) 0.3736(6) 0.0419(16) Uani d . 1
H H10 0.8546 0.2856 0.3058 0.050 Uiso calc R 1
C C11 0.8886(4) 0.3112(6) 0.5531(7) 0.0464(16) Uani d . 1
H H11A 0.9396 0.2540 0.5788 0.056 Uiso calc R 1
H H11B 0.9242 0.3802 0.5690 0.056 Uiso calc R 1
C C12 0.7430(5) 0.2054(6) 0.3622(7) 0.0426(17) Uani d . 1
C C13 0.6013(6) 0.5188(6) 0.2430(9) 0.075(3) Uani d . 1
H H13A 0.6321 0.5573 0.1782 0.112 Uiso calc R 1
H H13B 0.6041 0.5629 0.3341 0.112 Uiso calc R 1
H H13C 0.5310 0.5026 0.1780 0.112 Uiso calc R 1
C C14 0.7476(5) 0.1136(6) 0.2939(8) 0.0520(17) Uani d . 1
H H14 0.6989 0.0624 0.2942 0.062 Uiso calc R 1
C C15 0.8197(7) 0.0789(7) 0.2155(11) 0.086(3) Uani d . 1
H H15A 0.8561 0.0154 0.2693 0.128 Uiso calc R 1
H H15B 0.8678 0.1360 0.2237 0.128 Uiso calc R 1
H H15C 0.7817 0.0628 0.1028 0.128 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 N1 C5 124.6(5)
C1 N1 H1 117.7
C5 N1 H1 117.7
C6 N2 H2A 112.5
C6 N2 H2B 113.9
H2A N2 H2B 113.3
H16 O2 H17 105.0
O1 C1 N1 118.2(6)
O1 C1 C2 125.6(6)
N1 C1 C2 116.2(5)
C3 C2 C1 120.2(6)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 121.9(6)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 117.9(6)
C5 C4 C6 121.0(5)
C3 C4 C6 121.1(6)
C4 C5 N1 119.2(5)
C4 C5 C11 125.6(5)
N1 C5 C11 115.2(5)
N2 C6 C12 113.2(5)
N2 C6 C7 108.6(5)
C12 C6 C7 108.6(5)
N2 C6 C4 109.5(5)
C12 C6 C4 108.1(5)
C7 C6 C4 108.7(5)
C8 C7 C6 114.9(5)
C8 C7 H7A 108.5
C6 C7 H7A 108.5
C8 C7 H7B 108.5
C6 C7 H7B 108.5
H7A C7 H7B 107.5
C9 C8 C13 122.4(7)
C9 C8 C7 120.9(6)
C13 C8 C7 116.6(7)
C8 C9 C10 124.2(6)
C8 C9 H9 117.9
C10 C9 H9 117.9
C9 C10 C12 110.9(5)
C9 C10 C11 111.3(5)
C12 C10 C11 107.9(5)
C9 C10 H10 108.9
C12 C10 H10 108.9
C11 C10 H10 108.9
C5 C11 C10 110.2(5)
C5 C11 H11A 109.6
C10 C11 H11A 109.6
C5 C11 H11B 109.6
C10 C11 H11B 109.6
H11A C11 H11B 108.1
C14 C12 C6 125.8(6)
C14 C12 C10 124.2(6)
C6 C12 C10 109.9(6)
C8 C13 H13A 109.5
C8 C13 H13B 109.5
H13A C13 H13B 109.5
C8 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 C15 129.0(7)
C12 C14 H14 115.5
C15 C14 H14 115.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.365(7)
N1 C5 1.371(7)
N1 H1 0.8600
N2 C6 1.455(8)
N2 H2A 0.8598
N2 H2B 0.8601
O1 C1 1.271(7)
O2 H16 0.8504
O2 H17 0.8500
C1 C2 1.393(8)
C2 C3 1.360(8)
C2 H2 0.9300
C3 C4 1.410(9)
C3 H3 0.9300
C4 C5 1.351(8)
C4 C6 1.553(8)
C5 C11 1.482(8)
C6 C12 1.498(9)
C6 C7 1.535(9)
C7 C8 1.488(10)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.321(9)
C8 C13 1.488(10)
C9 C10 1.490(9)
C9 H9 0.9300
C10 C12 1.523(9)
C10 C11 1.547(7)
C10 H10 0.9800
C11 H11A 0.9700
C11 H11B 0.9700
C12 C14 1.297(9)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.483(10)
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
O2 H17 O2 2_755 0.85 2.42 2.833(13) 111
O2 H16 O1 1_554 0.85 2.03 2.877(9) 174
N2 H2B O2 3_445 0.86 2.07 2.918(9) 168
N2 H2A N2 2_656 0.86 2.68 3.333(12) 134
N1 H1 O1 2_757 0.86 1.94 2.780(8) 165
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
C5 N1 C1 O1 -179.7(6)
C5 N1 C1 C2 0.6(9)
O1 C1 C2 C3 -179.9(7)
N1 C1 C2 C3 -0.2(10)
C1 C2 C3 C4 -0.2(11)
C2 C3 C4 C5 0.3(10)
C2 C3 C4 C6 178.9(6)
C3 C4 C5 N1 0.1(9)
C6 C4 C5 N1 -178.5(5)
C3 C4 C5 C11 179.1(7)
C6 C4 C5 C11 0.5(10)
C1 N1 C5 C4 -0.5(9)
C1 N1 C5 C11 -179.6(6)
C5 C4 C6 N2 143.9(6)
C3 C4 C6 N2 -34.6(8)
C5 C4 C6 C12 20.2(8)
C3 C4 C6 C12 -158.4(6)
C5 C4 C6 C7 -97.6(7)
C3 C4 C6 C7 83.8(7)
N2 C6 C7 C8 -166.0(5)
C12 C6 C7 C8 -42.5(7)
C4 C6 C7 C8 74.9(7)
C6 C7 C8 C9 11.2(9)
C6 C7 C8 C13 -168.6(6)
C13 C8 C9 C10 -179.6(6)
C7 C8 C9 C10 0.7(9)
C8 C9 C10 C12 19.4(7)
C8 C9 C10 C11 -100.7(7)
C4 C5 C11 C10 13.2(9)
N1 C5 C11 C10 -167.8(5)
C9 C10 C11 C5 75.4(7)
C12 C10 C11 C5 -46.4(7)
N2 C6 C12 C14 2.6(9)
C7 C6 C12 C14 -118.0(7)
C4 C6 C12 C14 124.2(7)
N2 C6 C12 C10 -176.6(5)
C7 C6 C12 C10 62.7(6)
C4 C6 C12 C10 -55.0(6)
C9 C10 C12 C14 129.5(6)
C11 C10 C12 C14 -108.4(7)
C9 C10 C12 C6 -51.2(6)
C11 C10 C12 C6 70.9(6)
C6 C12 C14 C15 -178.4(7)
C10 C12 C14 C15 0.7(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178482
