#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221553.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_2221553
loop_
_publ_author_name
'Löffler, Philipp M. G.'
'Ulven, Trond'
'Bond, Andrew D.'
_publ_section_title
;
 Ethyl
 2-(1,2,3,4-tetrahydrospiro[carbazole-3,2'-[1,3]dioxolan]-9-yl)acetate
;
_journal_coeditor_code           XU2485
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o685
_journal_paper_doi               10.1107/S160053680900748X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H21 N O4'
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_systematic
;
Ethyl 2-(1,2,3,4-tetrahydrospiro[carbazole-3,2'-[1,3]dioxolan]-9-yl)acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.6290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5533(4)
_cell_length_b                   17.3773(6)
_cell_length_c                   8.9637(3)
_cell_measurement_reflns_used    7203
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.00
_cell_volume                     1583.06(10)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker-Nonius X8 APEXII CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25055
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0396
_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)+(0.0568P)²+0.4296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                3174
_reflns_number_total             3851
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2485.cif
_cod_data_source_block           I
_cod_original_cell_volume        1583.05(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221553
_cod_database_fobs_code          2221553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 1.21234(9) 0.15818(7) 1.12008(10) 0.0460(3) Uani d . 1 . .
O O2 1.17774(8) 0.16828(5) 0.85930(9) 0.0310(2) Uani d . 1 . .
O O3 0.54620(9) 0.18009(6) 0.72948(11) 0.0431(2) Uani d . 1 . .
O O4 0.48419(8) 0.12028(5) 0.50032(10) 0.0319(2) Uani d . 1 . .
N N1 0.76683(9) 0.24098(6) 0.66065(11) 0.0269(2) Uani d . 1 . .
C C1 0.76918(11) 0.32014(7) 0.67550(13) 0.0271(2) Uani d . 1 . .
C C2 0.68683(13) 0.37599(8) 0.58858(16) 0.0375(3) Uani d . 1 . .
H H2A 0.6137 0.3624 0.5048 0.045 Uiso calc R 1 . .
C C3 0.71574(15) 0.45191(8) 0.62915(18) 0.0459(3) Uani d . 1 . .
H H3A 0.6611 0.4912 0.5719 0.055 Uiso calc R 1 . .
C C4 0.82262(15) 0.47257(8) 0.75148(18) 0.0428(3) Uani d . 1 . .
H H4A 0.8399 0.5254 0.7756 0.051 Uiso calc R 1 . .
C C5 0.90393(13) 0.41716(7) 0.83833(15) 0.0339(3) Uani d . 1 . .
H H5A 0.9766 0.4316 0.9219 0.041 Uiso calc R 1 . .
C C6 0.87768(11) 0.33951(6) 0.80135(13) 0.0263(2) Uani d . 1 . .
C C7 0.93961(10) 0.26886(6) 0.86264(13) 0.0256(2) Uani d . 1 . .
C C8 1.06186(12) 0.25587(8) 0.99027(14) 0.0324(3) Uani d . 1 . .
H H8A 1.0427 0.2630 1.0916 0.039 Uiso calc R 1 . .
H H8B 1.1296 0.2940 0.9825 0.039 Uiso calc R 1 . .
C C9 1.11382(11) 0.17469(7) 0.98003(13) 0.0305(3) Uani d . 1 . .
C C10 1.00563(12) 0.11489(7) 0.95185(14) 0.0334(3) Uani d . 1 . .
H H10A 0.9625 0.1170 1.0371 0.040 Uiso calc R 1 . .
H H10B 1.0448 0.0631 0.9526 0.040 Uiso calc R 1 . .
C C11 0.90183(12) 0.12724(7) 0.79701(14) 0.0311(3) Uani d . 1 . .
H H11A 0.9359 0.1086 0.7109 0.037 Uiso calc R 1 . .
H H11B 0.8213 0.0977 0.7958 0.037 Uiso calc R 1 . .
C C12 0.86989(10) 0.21090(6) 0.77637(13) 0.0255(2) Uani d . 1 . .
C C13 1.33628(14) 0.16069(11) 1.09153(17) 0.0486(4) Uani d . 1 . .
H H13A 1.3774 0.1090 1.1043 0.058 Uiso calc R 1 . .
H H13B 1.3950 0.1968 1.1636 0.058 Uiso calc R 1 . .
C C14 1.31189(12) 0.18790(9) 0.92705(15) 0.0398(3) Uani d . 1 . .
H H14A 1.3257 0.2441 0.9228 0.048 Uiso calc R 1 . .
H H14B 1.3704 0.1612 0.8740 0.048 Uiso calc R 1 . .
C C15 0.67326(11) 0.19717(7) 0.54503(13) 0.0290(2) Uani d . 1 . .
H H15A 0.7192 0.1537 0.5107 0.035 Uiso calc R 1 . .
H H15B 0.6361 0.2304 0.4540 0.035 Uiso calc R 1 . .
C C16 0.56219(11) 0.16596(6) 0.60498(13) 0.0264(2) Uani d . 1 . .
C C17 0.37837(12) 0.08256(8) 0.54942(15) 0.0373(3) Uani d . 1 . .
H H17A 0.3230 0.1215 0.5826 0.045 Uiso calc R 1 . .
H H17B 0.4156 0.0477 0.6377 0.045 Uiso calc R 1 . .
C C18 0.29786(13) 0.03789(8) 0.41509(16) 0.0407(3) Uani d . 1 . .
H H18A 0.2259 0.0120 0.4450 0.061 Uiso calc R 1 . .
H H18B 0.3534 -0.0006 0.3835 0.061 Uiso calc R 1 . .
H H18C 0.2613 0.0729 0.3285 0.061 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'
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
C13 O1 C9 . . 109.16(9) ?
C14 O2 C9 . . 106.09(9) ?
C16 O4 C17 . . 115.65(9) ?
C1 N1 C12 . . 108.24(9) ?
C1 N1 C15 . . 125.89(10) ?
C12 N1 C15 . . 125.87(10) ?
N1 C1 C2 . . 130.37(11) ?
N1 C1 C6 . . 107.66(10) ?
C2 C1 C6 . . 121.97(11) ?
C3 C2 C1 . . 117.28(13) ?
C3 C2 H2A . . 121.4 ?
C1 C2 H2A . . 121.4 ?
C2 C3 C4 . . 121.92(13) ?
C2 C3 H3A . . 119.0 ?
C4 C3 H3A . . 119.0 ?
C5 C4 C3 . . 120.83(13) ?
C5 C4 H4A . . 119.6 ?
C3 C4 H4A . . 119.6 ?
C4 C5 C6 . . 119.03(12) ?
C4 C5 H5A . . 120.5 ?
C6 C5 H5A . . 120.5 ?
C5 C6 C1 . . 118.98(11) ?
C5 C6 C7 . . 134.14(11) ?
C1 C6 C7 . . 106.87(10) ?
C12 C7 C6 . . 107.24(10) ?
C12 C7 C8 . . 123.20(11) ?
C6 C7 C8 . . 129.47(10) ?
C7 C8 C9 . . 110.13(10) ?
C7 C8 H8A . . 109.6 ?
C9 C8 H8A . . 109.6 ?
C7 C8 H8B . . 109.6 ?
C9 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
O2 C9 O1 . . 105.70(9) ?
O2 C9 C10 . . 108.03(10) ?
O1 C9 C10 . . 110.29(10) ?
O2 C9 C8 . . 111.67(10) ?
O1 C9 C8 . . 108.76(10) ?
C10 C9 C8 . . 112.19(10) ?
C9 C10 C11 . . 112.18(10) ?
C9 C10 H10A . . 109.2 ?
C11 C10 H10A . . 109.2 ?
C9 C10 H10B . . 109.2 ?
C11 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 109.32(10) ?
C12 C11 H11A . . 109.8 ?
C10 C11 H11A . . 109.8 ?
C12 C11 H11B . . 109.8 ?
C10 C11 H11B . . 109.8 ?
H11A C11 H11B . . 108.3 ?
C7 C12 N1 . . 109.97(10) ?
C7 C12 C11 . . 125.57(10) ?
N1 C12 C11 . . 124.41(10) ?
O1 C13 C14 . . 105.53(11) ?
O1 C13 H13A . . 110.6 ?
C14 C13 H13A . . 110.6 ?
O1 C13 H13B . . 110.6 ?
C14 C13 H13B . . 110.6 ?
H13A C13 H13B . . 108.8 ?
O2 C14 C13 . . 103.35(10) ?
O2 C14 H14A . . 111.1 ?
C13 C14 H14A . . 111.1 ?
O2 C14 H14B . . 111.1 ?
C13 C14 H14B . . 111.1 ?
H14A C14 H14B . . 109.1 ?
N1 C15 C16 . . 112.31(9) ?
N1 C15 H15A . . 109.1 ?
C16 C15 H15A . . 109.1 ?
N1 C15 H15B . . 109.1 ?
C16 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.9 ?
O3 C16 O4 . . 124.27(10) ?
O3 C16 C15 . . 124.99(10) ?
O4 C16 C15 . . 110.74(9) ?
O4 C17 C18 . . 107.80(10) ?
O4 C17 H17A . . 110.1 ?
C18 C17 H17A . . 110.1 ?
O4 C17 H17B . . 110.1 ?
C18 C17 H17B . . 110.1 ?
H17A C17 H17B . . 108.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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 C13 . 1.3995(17) ?
O1 C9 . 1.4268(14) ?
O2 C14 . 1.4233(15) ?
O2 C9 . 1.4254(13) ?
O3 C16 . 1.1982(14) ?
O4 C16 . 1.3311(14) ?
O4 C17 . 1.4613(14) ?
N1 C1 . 1.3817(15) ?
N1 C12 . 1.3872(14) ?
N1 C15 . 1.4412(14) ?
C1 C2 . 1.3926(17) ?
C1 C6 . 1.4146(16) ?
C2 C3 . 1.381(2) ?
C2 H2A . 0.950 ?
C3 C4 . 1.392(2) ?
C3 H3A . 0.950 ?
C4 C5 . 1.382(2) ?
C4 H4A . 0.950 ?
C5 C6 . 1.3993(16) ?
C5 H5A . 0.950 ?
C6 C7 . 1.4293(16) ?
C7 C12 . 1.3591(16) ?
C7 C8 . 1.4929(15) ?
C8 C9 . 1.5252(18) ?
C8 H8A . 0.990 ?
C8 H8B . 0.990 ?
C9 C10 . 1.5140(18) ?
C10 C11 . 1.5340(17) ?
C10 H10A . 0.990 ?
C10 H10B . 0.990 ?
C11 C12 . 1.4926(16) ?
C11 H11A . 0.990 ?
C11 H11B . 0.990 ?
C13 C14 . 1.503(2) ?
C13 H13A . 0.990 ?
C13 H13B . 0.990 ?
C14 H14A . 0.990 ?
C14 H14B . 0.990 ?
C15 C16 . 1.5154(15) ?
C15 H15A . 0.990 ?
C15 H15B . 0.990 ?
C17 C18 . 1.4910(18) ?
C17 H17A . 0.990 ?
C17 H17B . 0.990 ?
C18 H18A . 0.980 ?
C18 H18B . 0.980 ?
C18 H18C . 0.980 ?
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 . . . . -179.74(11) ?
C15 N1 C1 C2 . . . . 0.15(19) ?
C12 N1 C1 C6 . . . . 1.15(12) ?
C15 N1 C1 C6 . . . . -178.96(9) ?
N1 C1 C2 C3 . . . . -178.46(12) ?
C6 C1 C2 C3 . . . . 0.54(18) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . -0.5(2) ?
C3 C4 C5 C6 . . . . 0.20(19) ?
C4 C5 C6 C1 . . . . 0.41(16) ?
C4 C5 C6 C7 . . . . 179.11(12) ?
N1 C1 C6 C5 . . . . 178.40(10) ?
C2 C1 C6 C5 . . . . -0.80(16) ?
N1 C1 C6 C7 . . . . -0.62(11) ?
C2 C1 C6 C7 . . . . -179.82(10) ?
C5 C6 C7 C12 . . . . -178.95(12) ?
C1 C6 C7 C12 . . . . -0.15(12) ?
C5 C6 C7 C8 . . . . -2.3(2) ?
C1 C6 C7 C8 . . . . 176.51(11) ?
C12 C7 C8 C9 . . . . 14.73(15) ?
C6 C7 C8 C9 . . . . -161.45(11) ?
C14 O2 C9 O1 . . . . -29.21(13) ?
C14 O2 C9 C10 . . . . -147.26(10) ?
C14 O2 C9 C8 . . . . 88.91(12) ?
C13 O1 C9 O2 . . . . 14.11(14) ?
C13 O1 C9 C10 . . . . 130.64(12) ?
C13 O1 C9 C8 . . . . -105.93(13) ?
C7 C8 C9 O2 . . . . 76.13(12) ?
C7 C8 C9 O1 . . . . -167.60(9) ?
C7 C8 C9 C10 . . . . -45.32(13) ?
O2 C9 C10 C11 . . . . -61.20(12) ?
O1 C9 C10 C11 . . . . -176.27(9) ?
C8 C9 C10 C11 . . . . 62.32(13) ?
C9 C10 C11 C12 . . . . -43.12(13) ?
C6 C7 C12 N1 . . . . 0.87(12) ?
C8 C7 C12 N1 . . . . -176.05(9) ?
C6 C7 C12 C11 . . . . 178.28(10) ?
C8 C7 C12 C11 . . . . 1.36(17) ?
C1 N1 C12 C7 . . . . -1.28(12) ?
C15 N1 C12 C7 . . . . 178.83(10) ?
C1 N1 C12 C11 . . . . -178.72(10) ?
C15 N1 C12 C11 . . . . 1.39(16) ?
C10 C11 C12 C7 . . . . 12.73(15) ?
C10 C11 C12 N1 . . . . -170.22(10) ?
C9 O1 C13 C14 . . . . 5.60(16) ?
C9 O2 C14 C13 . . . . 31.96(14) ?
O1 C13 C14 O2 . . . . -23.07(16) ?
C1 N1 C15 C16 . . . . -97.30(13) ?
C12 N1 C15 C16 . . . . 82.58(13) ?
C17 O4 C16 O3 . . . . -3.87(17) ?
C17 O4 C16 C15 . . . . 176.02(10) ?
N1 C15 C16 O3 . . . . 5.41(17) ?
N1 C15 C16 O4 . . . . -174.47(9) ?
C16 O4 C17 C18 . . . . 176.84(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9658697
