#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/08/2100845.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_2100845
loop_
_publ_author_name
'Ianelli, S.'
'Nardelli, M.'
'Belletti, D.'
'Jamart-Grégoire, B.'
'Mouaddib, A.'
'Caubère, P.'
_publ_section_title
;
 Synthesis and structure of new bronchospasmolytic agents. II
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              687
_journal_page_last               695
_journal_paper_doi               10.1107/S0108768192002647
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C17 H23 N O2'
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.4
_chemical_name_systematic
;
   1-hydroxy-8-morpholino-tricyclo[6.5.0.02,7]trideca-2,4,6-triene
                                        (compound 2)
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 90.01(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.740(5)
_cell_length_b                   12.26(3)
_cell_length_c                   18.524(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     1531(4)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia)'
_computing_data_collection       'CAD4 (Enraf-Nonius'
_computing_data_reduction        'DIFAU (Ugozzoli et al.)'
_computing_molecular_graphics    'ORTEP (Johnson)'
_computing_structure_refinement  'SHELX76 (Sheldrick)'
_computing_structure_solution    'SHELX86 (Sheldrick)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       CAD4
_diffrn_measurement_method       'theta-2theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard Molybdenum anode'
_diffrn_radiation_type           'Xray MoKalpha mean'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2674
_diffrn_reflns_reduction_process
;
     Only one quadrant of data (an asymmetric set) was measured
;
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  160
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.0719
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.1864
_exptl_crystal_description
;
      Short prism 0.26x0.31x0.59 mm. Crystals are air stable.
;
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.08
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   0.7921
_refine_ls_hydrogen_treatment    refined
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     273
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0372
_refine_ls_shift/esd_max         0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[s2(Fo)+0.0005*Fo2]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0435
_reflns_number_observed          1556
_reflns_number_total             2674
_reflns_observed_criterion       2.0sigma(I)
_cod_data_source_file            ge0307.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_matrix_type' tag value 'full-matrix' was replaced with
'full' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[s2(Fo)+0.0005*Fo2]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[s2(Fo)+0.0005*Fo2]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1530(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2100845
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_attached_atom
_atom_site_type_symbol
N .0350(3) .87990(10) .20471(9) .0344(6) Uani . N
O1 .3873(3) .8426(2) .26210(10) .0520(7) Uani . O
O2 -.0593(3) .8882(2) .05492(9) .0611(7) Uani . O
C1 .1576(3) .7967(2) .36060(10) .0348(7) Uani . C
C2 .1933(4) .7217(2) .41490(10) .0449(9) Uani . C
C3 .0319(4) .6612(2) .43740(10) .0491(9) Uani . C
C4 -.1559(4) .6749(2) .40720(10) .0485(9) Uani . C
C5 -.1909(4) .7505(2) .35290(10) .0429(9) Uani . C
C6 -.0281(3) .8108(2) .33040(10) .0337(8) Uani . C
C7 .0351(3) .9061(2) .28270(10) .0328(8) Uani . C
C8 .2556(3) .8848(2) .31540(10) .0373(7) Uani . C
C9 .3663(4) .9763(3) .3537(2) .0506(11) Uani . C
C10 .2755(5) 1.0196(3) .4232(2) .0581(11) Uani . C
C11 .0982(5) 1.0957(3) .4138(2) .0617(11) Uani . C
C12 -.0853(4) 1.0430(3) .3803(2) .0523(10) Uani . C
C13 -.0659(4) 1.0148(2) .30050(10) .0442(9) Uani . C
C14 -.1556(4) .8390(2) .17680(10) .0468(9) Uani . C
C15 -.1298(5) .8023(3) .10010(10) .0579(11) Uani . C
C16 .1248(4) .9279(3) .08220(10) .0531(10) Uani . C
C17 .1031(4) .9696(2) .15830(10) .0435(9) Uani . C
H1O .314(5) .813(3) .2292(19) .100(13) Uiso O1 H
H2 .325(4) .712(2) .4363(13) .060(8) Uiso C2 H
H3 .044(4) .6071(19) .4759(13) .051(7) Uiso C3 H
H4 -.266(4) .6304(19) .4268(12) .049(7) Uiso C4 H
H5 -.314(4) .7602(19) .3331(12) .050(7) Uiso C5 H
H91 .489(4) .9453(19) .3653(12) .049(7) Uiso C9 H
H92 .389(4) 1.039(2) .3202(13) .051(7) Uiso C9 H
H101 .237(4) .954(2) .4559(13) .058(8) Uiso C10 H
H102 .375(4) 1.059(2) .4484(14) .067(8) Uiso C10 H
H111 .139(4) 1.166(2) .3792(14) .068(8) Uiso C11 H
H112 .065(4) 1.126(2) .4625(15) .068(8) Uiso C11 H
H121 -.122(3) .975(2) .4086(12) .047(7) Uiso C12 H
H122 -.197(4) 1.094(2) .3853(13) .059(8) Uiso C12 H
H131 .009(3) 1.0753(19) .2753(12) .044(7) Uiso C13 H
H132 -.197(4) 1.012(2) .2769(12) .054(7) Uiso C13 H
H141 -.192(4) .775(2) .2091(13) .060(8) Uiso C14 H
H142 -.256(4) .899(2) .1789(14) .064(8) Uiso C14 H
H151 -.264(4) .782(2) .0805(14) .067(9) Uiso C15 H
H152 -.033(4) .740(3) .0986(15) .075(10) Uiso C15 H
H161 .159(4) .986(2) .0489(12) .047(7) Uiso C16 H
H162 .235(4) .867(2) .0802(15) .075(9) Uiso C16 H
H171 .002(4) 1.033(2) .1581(12) .056(7) Uiso C17 H
H172 .230(4) .998(2) .1754(13) .057(8) Uiso C17 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N Nitrogen .004 .003 'IT.4 Tab. 2.2A 2.3.1'
O Oxygen .008 .006 'IT.4 Tab. 2.2A 2.3.1'
C Carbon .002 .002 'IT.4 Tab. 2.2A 2.3.1'
H Hydrogen .000 .000 'IT.4 Tab. 2.2C'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 6 9
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
N O1 2.641(3)
N O2 2.848(2)
N C6 2.514(2)
N C8 2.533(3)
N C13 2.520(3)
N C15 2.428(3)
N C16 2.421(3)
O1 C1 2.458(3)
O1 C7 2.527(3)
O1 C9 2.363(4)
O2 C14 2.426(3)
O2 C17 2.421(3)
C1 C3 2.346(4)
C1 C4 2.727(4)
C1 C5 2.421(3)
C1 C7 2.136(3)
C1 C9 2.616(5)
C2 C4 2.427(4)
C2 C5 2.854(4)
C2 C6 2.422(3)
C2 C8 2.752(4)
C3 C5 2.430(4)
C3 C6 2.731(4)
C4 C6 2.353(4)
C5 C7 2.766(4)
C6 C8 2.135(3)
C6 C13 2.574(6)
C6 C14 2.993(3)
C7 C9 2.729(3)
C7 C12 2.597(4)
C7 C14 2.485(3)
C7 C17 2.475(3)
C8 C10 2.596(4)
C8 C13 2.704(4)
C9 C11 2.579(4)
C10 C12 2.574(4)
C11 C13 2.571(4)
C13 C17 2.924(3)
C14 C16 2.798(4)
C14 C17 2.391(4)
C15 C16 2.329(5)
C15 C17 2.798(5)
