#------------------------------------------------------------------------------
#$Date: 2018-06-14 15:53:24 +0300 (Thu, 14 Jun 2018) $
#$Revision: 208377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/08/2100848.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_2100848
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         ' C21 H32 N2 O2      '
_chemical_formula_sum            'C21 H32 N2 O2'
_chemical_formula_weight         344.50
_chemical_name_systematic
;
   3-diethylamino-1-hydroxy-8-morpholino-tricyclo[6.5.0.02,7]trideca-
   -2,4,6-triene                (compound 5)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 100.81(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0170(10)
_cell_length_b                   10.823(2)
_cell_length_c                   18.143(3)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293
_cell_measurement_theta_max      37
_cell_measurement_theta_min      18
_cell_volume                     1932.1(5)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia)'
_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       SIEMENS-AED
_diffrn_measurement_method       theta-2theta
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'standard Nickel anode'
_diffrn_radiation_type           'Xray CuKalpha mean'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4099
_diffrn_reflns_reduction_process
;
    Only one quadrant of data (an asymmetric set) was measured.
;
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    .5603
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description
;
?
;
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.07
_refine_diff_density_min         -0.08
_refine_ls_extinction_method     'according Zachariasen'
_refine_ls_goodness_of_fit_obs   0.9179
_refine_ls_hydrogen_treatment    'not refined'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0445
_refine_ls_shift/esd_max         0.04
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.0467
_reflns_number_observed          2276
_reflns_number_total             4099
_reflns_observed_criterion       2.0sigma(I)
_cod_data_source_file            ge0307.cif
_cod_data_source_block           5
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-15
;
_cod_original_cell_volume        1932.0(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        ' C21 H32 N2 O2      '
_cod_database_code               2100848
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
N1 -.7225(2) .0515(2) -.88910(10) .0376(8) Uani . . N
O1 -.9141(2) -.1126(2) -.93400(10) .0437(7) Uani . . O
O2 -.7221(3) .3076(2) -.92670(10) .0633(9) Uani . . O
C1 -.7846(3) -.2009(3) -.8145(2) .0349(9) Uani . . C
C2 -.8340(3) -.2763(3) -.7623(2) .0397(10) Uani . . C
C3 -.7688(3) -.2560(3) -.6868(2) .0512(12) Uani . . C
C4 -.6649(4) -.1703(3) -.6667(2) .0557(12) Uani . . C
C5 -.6169(3) -.0972(3) -.7188(2) .0481(11) Uani . . C
C6 -.6821(3) -.1158(3) -.7923(2) .0374(10) Uani . . C
C7 -.6720(3) -.0757(3) -.8710(2) .0346(10) Uani . . C
C8 -.7925(3) -.1728(3) -.8985(2) .0349(9) Uani . . C
C9 -.7693(3) -.2768(3) -.9513(2) .0461(12) Uani . . C
C10 -.6603(4) -.3725(3) -.9212(2) .0569(13) Uani . . C
C11 -.5132(3) -.3318(3) -.9215(2) .0562(13) Uani . . C
C12 -.4651(3) -.2237(3) -.8690(2) .0551(12) Uani . . C
C13 -.5330(3) -.0991(3) -.8930(2) .0464(11) Uani . . C
C14 -.6667(3) .1446(3) -.8331(2) .0484(11) Uani . . C
C15 -.7352(4) .2680(3) -.8534(2) .0593(13) Uani . . C
C16 -.7796(4) .2171(3) -.9807(2) .0609(14) Uani . . C
C17 -.7086(3) .0945(3) -.9645(2) .0494(12) Uani . . C
N2 -.9353(3) -.3632(2) -.77980(10) .0502(9) Uani . . N
C22 -.9734(3) -.4416(3) -.7210(2) .0569(14) Uani . . C
C23 -.8712(4) -.5440(3) -.6953(2) .0673(15) Uani . . C
C24 -1.0277(3) -.3642(3) -.8515(2) .0512(12) Uani . . C
C25 -1.0290(5) -.4848(3) -.8942(2) .0763(17) Uani . . C
H1O -.9203 -.0364 -.9085 .080 Uiso calc O1 H
H3 -.8012 -.3095 -.6431 .074(11) Uiso . C3 H
H4 -.6198 -.1603 -.6081 .065(10) Uiso . C4 H
H5 -.5356 -.0313 -.7034 .071(11) Uiso . C5 H
H91 -.7413 -.2349 -1.0003 .060(10) Uiso . C9 H
H92 -.8644 -.3255 -.9675 .061(10) Uiso . C9 H
H101 -.6805 -.4547 -.9551 .094(13) Uiso . C10 H
H102 -.6685 -.3937 -.8640 .068(11) Uiso . C10 H
H111 -.4470 -.4096 -.9046 .085(12) Uiso . C11 H
H112 -.5062 -.3049 -.9780 .054(9) Uiso . C11 H
H121 -.3570 -.2132 -.8659 .093(13) Uiso . C12 H
H122 -.4852 -.2462 -.8141 .062(10) Uiso . C12 H
H131 -.5467 -.0932 -.9534 .051(9) Uiso . C13 H
H132 -.4648 -.0270 -.8680 .069(10) Uiso . C13 H
H141 -.5588 .1537 -.8314 .072(11) Uiso . C14 H
H142 -.6841 .1160 -.7786 .057(9) Uiso . C14 H
H151 -.8418 .2596 -.8513 .071(11) Uiso . C15 H
H152 -.6892 .3364 -.8131 .084(12) Uiso . C15 H
H161 -.7690 .2480 -1.0359 .090(13) Uiso . C16 H
H162 -.8860 .2060 -.9787 .066(10) Uiso . C16 H
H171 -.7540 .0276 -1.0059 .062(10) Uiso . C17 H
H172 -.6022 .1049 -.9667 .056(9) Uiso . C17 H
H221 -1.0709 -.4831 -.7426 .075(11) Uiso . C22 H
H222 -.9812 -.3842 -.6733 .063(10) Uiso . C22 H
H231 -.9049 -.5981 -.6522 .091(13) Uiso . C23 H
H232 -.8630 -.6028 -.7424 .124(18) Uiso . C23 H
H233 -.7732 -.5039 -.6731 .107(15) Uiso . C23 H
H241 -.9984 -.2911 -.8858 .049(8) Uiso . C24 H
H242 -1.1292 -.3470 -.8418 .055(9) Uiso . C24 H
H251 -1.1000 -.4780 -.9468 .132(18) Uiso . C25 H
H252 -.9285 -.5031 -.9051 .114(17) Uiso . C25 H
H253 -1.0593 -.5591 -.8612 .112(15) Uiso . C25 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N Nitrogen .029 .018 'IT.4 Tab. 2.2A 2.3.1'
O Oxygen .047 .032 'IT.4 Tab. 2.2A 2.3.1'
C Carbon .017 .009 '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
-9 2 2
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
N1 O1 2.630(2)
N1 O2 2.854(3)
N1 C6 2.502(3)
N1 C8 2.523(3)
N1 C13 2.513(3)
N1 C15 2.441(4)
N1 C16 2.438(4)
O1 C1 2.499(3)
O1 C7 2.512(3)
O1 C9 2.352(3)
O2 C14 2.439(3)
O2 C17 2.417(3)
C1 C3 2.369(4)
C1 C4 2.744(3)
C1 C5 2.450(3)
C1 C7 2.144(4)
C1 C9 2.646(4)
C1 N2 2.474(3)
C1 C24 2.982(4)
C2 C4 2.467(4)
C2 C5 2.909(4)
C2 C6 2.437(4)
C2 C8 2.814(4)
C2 C22 2.471(4)
C2 C24 2.473(4)
C3 C5 2.437(4)
C3 C6 2.710(4)
C3 N2 2.433(3)
C3 C22 2.853(4)
C4 C6 2.328(4)
C5 C7 2.723(3)
C6 C8 2.125(3)
C6 C13 2.573(4)
C6 C14 2.925(4)
C7 C9 2.698(4)
C7 C12 2.614(4)
C7 C14 2.479(4)
C7 C17 2.483(4)
C8 C10 2.607(4)
C8 C13 2.703(4)
C9 C11 2.590(4)
C10 C12 2.573(4)
C11 C13 2.587(4)
C13 C17 2.883(4)
C14 C16 2.816(4)
C14 C17 2.405(4)
C15 C16 2.334(5)
C15 C17 2.805(4)
N2 C23 2.494(4)
N2 C25 2.487(4)
C22 C24 2.474(4)
