#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221231.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_2221231
loop_
_publ_author_name
'Bjerrum, Janni Vester'
'Ulven, Trond'
'Bond, Andrew D.'
_publ_section_title
;
 1,2-Dihydrospiro[carbazole-3(4H),2'-[1,3]dioxolane]
;
_journal_coeditor_code           YA2088
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o579
_journal_paper_doi               10.1107/S1600536809005558
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H15 N O2'
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_name_systematic
;
1,2-Dihydrospiro[carbazole-3(4H),2'-[1,3]dioxolane]
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 115.232(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3781(6)
_cell_length_b                   6.1467(4)
_cell_length_c                   10.5740(7)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.4
_cell_volume                     551.38(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_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      180(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker--Nonius X8 APEXII CCD'
_diffrn_measurement_method       'Thin-slice ω and φ'
_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  0.017
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7776
_diffrn_reflns_theta_full        28.4
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_min         3.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.030
_refine_ls_R_factor_gt           0.029
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.079
_refine_ls_wR_factor_ref         0.080
_reflns_number_gt                1427
_reflns_number_total             1485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2088.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2221231
_cod_database_fobs_code          2221231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.23032(12) 0.56670(18) 0.55448(11) 0.0256(2) Uani d . 1 . .
O O2 0.36610(11) 0.26085(18) 0.56040(10) 0.0238(2) Uani d . 1 . .
N N1 0.10724(14) -0.0286(2) 0.12685(12) 0.0259(3) Uani d . 1 . .
H H1A 0.0579 -0.1545 0.1083 0.031 Uiso calc R 1 . .
C C1 0.17592(15) 0.0682(3) 0.04893(14) 0.0240(3) Uani d . 1 . .
C C2 0.18695(18) -0.0023(3) -0.07194(15) 0.0321(3) Uani d . 1 . .
H H2A 0.1415 -0.1362 -0.1153 0.038 Uiso calc R 1 . .
C C3 0.2665(2) 0.1299(4) -0.12652(16) 0.0373(4) Uani d . 1 . .
H H3A 0.2752 0.0863 -0.2092 0.045 Uiso calc R 1 . .
C C4 0.3344(2) 0.3267(3) -0.06233(18) 0.0368(4) Uani d . 1 . .
H H4A 0.3891 0.4134 -0.1017 0.044 Uiso calc R 1 . .
C C5 0.32330(18) 0.3972(3) 0.05741(15) 0.0296(3) Uani d . 1 . .
H H5A 0.3694 0.5312 0.1000 0.036 Uiso calc R 1 . .
C C6 0.24301(15) 0.2675(3) 0.11475(13) 0.0223(3) Uani d . 1 . .
C C7 0.21109(15) 0.2855(2) 0.23567(13) 0.0206(3) Uani d . 1 . .
C C8 0.25187(17) 0.4636(2) 0.34150(14) 0.0229(3) Uani d . 1 . .
H H8A 0.1820 0.5900 0.3001 0.027 Uiso calc R 1 . .
H H8B 0.3620 0.5107 0.3687 0.027 Uiso calc R 1 . .
C C9 0.23321(15) 0.3857(2) 0.47164(14) 0.0202(3) Uani d . 1 . .
C C10 0.08364(15) 0.2549(3) 0.43550(14) 0.0235(3) Uani d . 1 . .
H H10A -0.0086 0.3484 0.3823 0.028 Uiso calc R 1 . .
H H10B 0.0775 0.2110 0.5231 0.028 Uiso calc R 1 . .
C C11 0.07498(17) 0.0513(2) 0.34942(15) 0.0249(3) Uani d . 1 . .
H H11A 0.1428 -0.0641 0.4112 0.030 Uiso calc R 1 . .
H H11B -0.0347 -0.0034 0.3056 0.030 Uiso calc R 1 . .
C C12 0.12847(15) 0.1046(2) 0.23882(13) 0.0217(3) Uani d . 1 . .
C C13 0.39081(17) 0.6225(3) 0.63924(16) 0.0275(3) Uani d . 1 . .
H H13A 0.4055 0.6671 0.7340 0.033 Uiso calc R 1 . .
H H13B 0.4255 0.7426 0.5965 0.033 Uiso calc R 1 . .
C C14 0.48246(17) 0.4138(3) 0.64530(17) 0.0303(3) Uani d . 1 . .
H H14A 0.5615 0.4393 0.6079 0.036 Uiso calc R 1 . .
H H14B 0.5372 0.3606 0.7427 0.036 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C13 . . 106.42(10) ?
C9 O2 C14 . . 106.18(11) ?
C1 N1 C12 . . 108.84(12) ?
C1 N1 H1A . . 125.6 ?
C12 N1 H1A . . 125.6 ?
N1 C1 C2 . . 130.52(15) ?
N1 C1 C6 . . 107.60(12) ?
C2 C1 C6 . . 121.87(14) ?
C3 C2 C1 . . 117.59(16) ?
C3 C2 H2A . . 121.2 ?
C1 C2 H2A . . 121.2 ?
C2 C3 C4 . . 121.30(15) ?
C2 C3 H3A . . 119.3 ?
C4 C3 H3A . . 119.3 ?
C5 C4 C3 . . 121.20(16) ?
C5 C4 H4A . . 119.4 ?
C3 C4 H4A . . 119.4 ?
C4 C5 C6 . . 118.84(16) ?
C4 C5 H5A . . 120.6 ?
C6 C5 H5A . . 120.6 ?
C5 C6 C1 . . 119.19(13) ?
C5 C6 C7 . . 134.15(14) ?
C1 C6 C7 . . 106.65(12) ?
C12 C7 C6 . . 107.16(13) ?
C12 C7 C8 . . 123.08(12) ?
C6 C7 C8 . . 129.75(12) ?
C7 C8 C9 . . 110.64(11) ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
O2 C9 O1 . . 104.87(11) ?
O2 C9 C10 . . 109.62(11) ?
O1 C9 C10 . . 108.13(11) ?
O2 C9 C8 . . 110.90(10) ?
O1 C9 C8 . . 110.32(11) ?
C10 C9 C8 . . 112.68(11) ?
C9 C10 C11 . . 113.10(11) ?
C9 C10 H10A . . 109.0 ?
C11 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
C11 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C10 . . 109.68(12) ?
C12 C11 H11A . . 109.7 ?
C10 C11 H11A . . 109.7 ?
C12 C11 H11B . . 109.7 ?
C10 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
C7 C12 N1 . . 109.75(12) ?
C7 C12 C11 . . 125.61(13) ?
N1 C12 C11 . . 124.58(13) ?
O1 C13 C14 . . 104.37(12) ?
O1 C13 H13A . . 110.9 ?
C14 C13 H13A . . 110.9 ?
O1 C13 H13B . . 110.9 ?
C14 C13 H13B . . 110.9 ?
H13A C13 H13B . . 108.9 ?
O2 C14 C13 . . 105.08(11) ?
O2 C14 H14A . . 110.7 ?
C13 C14 H14A . . 110.7 ?
O2 C14 H14B . . 110.7 ?
C13 C14 H14B . . 110.7 ?
H14A C14 H14B . . 108.8 ?
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
O1 C9 . 1.4234(17) ?
O1 C13 . 1.4270(17) ?
O2 C9 . 1.4233(16) ?
O2 C14 . 1.4303(18) ?
N1 C1 . 1.3785(19) ?
N1 C12 . 1.3822(18) ?
N1 H1A . 0.880 ?
C1 C2 . 1.395(2) ?
C1 C6 . 1.417(2) ?
C2 C3 . 1.384(3) ?
C2 H2A . 0.950 ?
C3 C4 . 1.400(3) ?
C3 H3A . 0.950 ?
C4 C5 . 1.383(2) ?
C4 H4A . 0.950 ?
C5 C6 . 1.400(2) ?
C5 H5A . 0.950 ?
C6 C7 . 1.4364(18) ?
C7 C12 . 1.3639(19) ?
C7 C8 . 1.4936(19) ?
C8 C9 . 1.5358(18) ?
C8 H8A . 0.990 ?
C8 H8B . 0.990 ?
C9 C10 . 1.5177(18) ?
C10 C11 . 1.529(2) ?
C10 H10A . 0.990 ?
C10 H10B . 0.990 ?
C11 C12 . 1.4922(18) ?
C11 H11A . 0.990 ?
C11 H11B . 0.990 ?
C13 C14 . 1.530(2) ?
C13 H13A . 0.990 ?
C13 H13B . 0.990 ?
C14 H14A . 0.990 ?
C14 H14B . 0.990 ?
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
N1 H1A C1 2_545 0.88 2.72 3.527(2) 154.1
C14 H14A C12 2_656 0.99 2.85 3.518(3) 125.9
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
C12 N1 C1 C2 . . . . 179.41(15) ?
C12 N1 C1 C6 . . . . 0.36(15) ?
N1 C1 C2 C3 . . . . -178.93(15) ?
C6 C1 C2 C3 . . . . 0.0(2) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C1 . . . . 0.2(2) ?
C4 C5 C6 C7 . . . . 178.70(16) ?
N1 C1 C6 C5 . . . . 178.86(13) ?
C2 C1 C6 C5 . . . . -0.3(2) ?
N1 C1 C6 C7 . . . . -0.06(15) ?
C2 C1 C6 C7 . . . . -179.21(13) ?
C5 C6 C7 C12 . . . . -178.94(16) ?
C1 C6 C7 C12 . . . . -0.27(14) ?
C5 C6 C7 C8 . . . . 2.5(3) ?
C1 C6 C7 C8 . . . . -178.84(13) ?
C12 C7 C8 C9 . . . . 16.67(18) ?
C6 C7 C8 C9 . . . . -164.96(13) ?
C14 O2 C9 O1 . . . . -34.81(13) ?
C14 O2 C9 C10 . . . . -150.69(12) ?
C14 O2 C9 C8 . . . . 84.26(13) ?
C13 O1 C9 O2 . . . . 36.02(13) ?
C13 O1 C9 C10 . . . . 152.93(12) ?
C13 O1 C9 C8 . . . . -83.44(13) ?
C7 C8 C9 O2 . . . . 79.85(14) ?
C7 C8 C9 O1 . . . . -164.41(11) ?
C7 C8 C9 C10 . . . . -43.46(16) ?
O2 C9 C10 C11 . . . . -64.65(14) ?
O1 C9 C10 C11 . . . . -178.44(11) ?
C8 C9 C10 C11 . . . . 59.37(16) ?
C9 C10 C11 C12 . . . . -42.89(16) ?
C6 C7 C12 N1 . . . . 0.49(15) ?
C8 C7 C12 N1 . . . . 179.18(12) ?
C6 C7 C12 C11 . . . . 177.82(13) ?
C8 C7 C12 C11 . . . . -3.5(2) ?
C1 N1 C12 C7 . . . . -0.54(15) ?
C1 N1 C12 C11 . . . . -177.90(13) ?
C10 C11 C12 C7 . . . . 16.12(19) ?
C10 C11 C12 N1 . . . . -166.94(12) ?
C9 O1 C13 C14 . . . . -22.68(15) ?
C9 O2 C14 C13 . . . . 20.17(14) ?
O1 C13 C14 O2 . . . . 1.51(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1228004
