#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:20:40 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/12/7061246.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061246
loop_
_publ_author_name
'Rodríguez, M. R.'
'Espino, G. A.'
'Piro, O. E.'
'Echeverría, G. A.'
'Parajón-Costa, B. S.'
'González-Baró, A. C.'
_publ_section_title
;
 The crystal structure and characterization of a co-product in the
 synthesis of a Schiff base give evidence of its zwitterionic nature in
 the solid state
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3130
_journal_page_last               3139
_journal_paper_doi               10.1039/D1NJ04537G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C21 H19 N O4 S'
_chemical_formula_weight         381.43
_chemical_name_systematic
(6R,12S)-4,10-dimethoxy-13-(thiophen-2-ylmethyl)-6,12-dihydro-6,12-epiminodibenzo[b,f][1,5]dioxocine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-09-13 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                99.480(5)
_cell_angle_beta                 102.576(5)
_cell_angle_gamma                112.887(7)
_cell_formula_units_Z            2
_cell_length_a                   9.2740(6)
_cell_length_b                   9.9087(7)
_cell_length_c                   11.3130(6)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      73.2469
_cell_measurement_theta_min      4.1639
_cell_volume                     898.10(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.405
_diffrn_reflns_theta_min         4.167
_exptl_absorpt_coefficient_mu    1.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       fragment
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.121
_refine_diff_density_max         1.149
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1496P)²+0.1581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2969
_reflns_number_total             3552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj04537g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7061246.cif.'
_cod_original_cell_volume        898.10(11)
_cod_database_code               7061246
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.520
_shelx_estimated_absorpt_t_max   0.808
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2513(3) 0.6235(3) -0.2398(2) 0.0345(5) Uani 1 1 d . . . . .
H1 H 0.1678 0.6557 -0.2250 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2499(3) 0.3704(3) -0.2371(2) 0.0341(5) Uani 1 1 d . . . . .
C12 C 0.1703(3) 0.2099(3) -0.2687(2) 0.0392(5) Uani 1 1 d . . . . .
C13 C 0.0142(4) 0.1331(3) -0.3555(3) 0.0499(6) Uani 1 1 d . . . . .
H13 H -0.0388 0.0271 -0.3788 0.060 Uiso 1 1 calc R U . . .
C14 C -0.0634(3) 0.2138(4) -0.4080(3) 0.0547(7) Uani 1 1 d . . . . .
H14 H -0.1677 0.1611 -0.4669 0.066 Uiso 1 1 calc R U . . .
C15 C 0.0115(3) 0.3702(3) -0.3742(2) 0.0467(6) Uani 1 1 d . . . . .
H15 H -0.0432 0.4226 -0.4088 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1703(3) 0.4510(3) -0.2878(2) 0.0365(5) Uani 1 1 d . . . . .
C17 C 0.1829(5) -0.0164(3) -0.2322(3) 0.0584(7) Uani 1 1 d . . . . .
H17A H 0.0770 -0.0494 -0.2191 0.088 Uiso 1 1 calc R U . . .
H17B H 0.2509 -0.0468 -0.1766 0.088 Uiso 1 1 calc R U . . .
H17C H 0.1695 -0.0620 -0.3180 0.088 Uiso 1 1 calc R U . . .
O1 O 0.4048(2) 0.44076(18) -0.15211(16) 0.0368(4) Uani 1 1 d . . . . .
O11 O 0.2591(3) 0.1459(2) -0.2066(2) 0.0484(5) Uani 1 1 d . . . . .
C2 C 0.4870(3) 0.6051(2) -0.1382(2) 0.0348(5) Uani 1 1 d . . . . .
H2 H 0.5847 0.6515 -0.0636 0.042 Uiso 1 1 calc R U . . .
C21 C 0.4562(3) 0.6812(3) -0.3382(2) 0.0370(5) Uani 1 1 d . . . . .
C22 C 0.5125(3) 0.7212(3) -0.4395(2) 0.0441(6) Uani 1 1 d . . . . .
C23 C 0.6522(4) 0.7069(3) -0.4526(3) 0.0530(7) Uani 1 1 d . . . . .
H23 H 0.6908 0.7323 -0.5190 0.064 Uiso 1 1 calc R U . . .
C24 C 0.7343(4) 0.6549(4) -0.3673(3) 0.0541(7) Uani 1 1 d . . . . .
H24 H 0.8262 0.6441 -0.3781 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6811(3) 0.6190(3) -0.2666(3) 0.0452(6) Uani 1 1 d . . . . .
H25 H 0.7376 0.5852 -0.2095 0.054 Uiso 1 1 calc R U . . .
C26 C 0.5416(3) 0.6339(2) -0.2512(2) 0.0367(5) Uani 1 1 d . . . . .
C27 C 0.4717(7) 0.8111(5) -0.6195(4) 0.0773(11) Uani 1 1 d . . . . .
H27A H 0.5817 0.8921 -0.5888 0.116 Uiso 1 1 calc R U . . .
H27B H 0.3986 0.8452 -0.6649 0.116 Uiso 1 1 calc R U . . .
H27C H 0.4694 0.7250 -0.6747 0.116 Uiso 1 1 calc R U . . .
O2 O 0.3166(2) 0.6940(2) -0.32992(16) 0.0396(4) Uani 1 1 d . . . . .
O21 O 0.4207(3) 0.7681(3) -0.5161(2) 0.0596(6) Uani 1 1 d . . . . .
C3 C 0.3252(3) 0.6557(3) -0.0114(2) 0.0399(5) Uani 1 1 d . . . . .
H3A H 0.4182 0.6782 0.0605 0.048 Uiso 1 1 calc R U . . .
H3B H 0.2477 0.5497 -0.0289 0.048 Uiso 1 1 calc R U . . .
C31 C 0.2443(3) 0.7548(3) 0.0211(2) 0.0367(5) Uani 1 1 d . . . . .
C32 C 0.0641(3) 0.7022(2) -0.0068(2) 0.0359(5) Uani 1 1 d . . . . .
H32 H -0.0190 0.6046 -0.0487 0.043 Uiso 1 1 calc R U . . .
C33 C 0.0455(4) 0.8384(4) 0.0464(3) 0.0570(7) Uani 1 1 d . . . . .
H33 H -0.0572 0.8356 0.0412 0.068 Uiso 1 1 calc R U . . .
C34 C 0.1855(5) 0.9665(3) 0.1026(3) 0.0576(7) Uani 1 1 d . . . . .
H34 H 0.1891 1.0591 0.1402 0.069 Uiso 1 1 calc R U . . .
S S 0.35450(10) 0.94226(9) 0.09814(8) 0.0581(3) Uani 1 1 d . . . . .
N N 0.3830(2) 0.6774(2) -0.12168(18) 0.0343(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 N 108.88(18) . . ?
O2 C1 C16 111.82(18) . . ?
N C1 C16 111.34(18) . . ?
O1 C11 C16 122.6(2) . . ?
O1 C11 C12 116.7(2) . . ?
C16 C11 C12 120.7(2) . . ?
O11 C12 C13 126.6(2) . . ?
O11 C12 C11 114.5(2) . . ?
C13 C12 C11 118.9(2) . . ?
C12 C13 C14 120.2(3) . . ?
C15 C14 C13 121.0(2) . . ?
C14 C15 C16 120.1(3) . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 C1 119.2(2) . . ?
C15 C16 C1 121.6(2) . . ?
C11 O1 C2 112.83(16) . . ?
C12 O11 C17 117.1(2) . . ?
N C2 O1 112.19(18) . . ?
N C2 C26 109.10(18) . . ?
O1 C2 C26 110.54(18) . . ?
O2 C21 C26 122.5(2) . . ?
O2 C21 C22 116.9(2) . . ?
C26 C21 C22 120.6(2) . . ?
O21 C22 C23 126.4(2) . . ?
O21 C22 C21 114.9(2) . . ?
C23 C22 C21 118.6(3) . . ?
C24 C23 C22 120.5(3) . . ?
C25 C24 C23 120.8(3) . . ?
C24 C25 C26 119.6(3) . . ?
C21 C26 C25 119.9(2) . . ?
C21 C26 C2 119.3(2) . . ?
C25 C26 C2 120.8(2) . . ?
C21 O2 C1 112.59(17) . . ?
C22 O21 C27 117.6(3) . . ?
N C3 C31 112.61(18) . . ?
C32 C31 C3 125.2(2) . . ?
C32 C31 S 112.92(17) . . ?
C3 C31 S 121.91(19) . . ?
C33 C32 C31 105.0(2) . . ?
C34 C33 C32 115.9(3) . . ?
C33 C34 S 112.9(2) . . ?
C34 S C31 93.26(14) . . ?
C2 N C1 107.56(18) . . ?
C2 N C3 112.45(18) . . ?
C1 N C3 114.02(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.438(3) . ?
C1 N 1.453(3) . ?
C1 C16 1.516(3) . ?
C11 O1 1.369(3) . ?
C11 C16 1.392(3) . ?
C11 C12 1.409(3) . ?
C12 O11 1.370(3) . ?
C12 C13 1.384(4) . ?
C13 C14 1.388(5) . ?
C14 C15 1.371(4) . ?
C15 C16 1.402(3) . ?
C17 O11 1.429(3) . ?
O1 C2 1.468(3) . ?
C2 N 1.432(3) . ?
C2 C26 1.503(3) . ?
C21 O2 1.370(3) . ?
C21 C26 1.385(3) . ?
C21 C22 1.412(3) . ?
C22 O21 1.345(4) . ?
C22 C23 1.393(4) . ?
C23 C24 1.387(5) . ?
C24 C25 1.382(4) . ?
C25 C26 1.402(3) . ?
C27 O21 1.422(4) . ?
C3 N 1.476(3) . ?
C3 C31 1.496(3) . ?
C31 C32 1.484(3) . ?
C31 S 1.690(2) . ?
C32 C33 1.474(4) . ?
C33 C34 1.340(5) . ?
C34 S 1.685(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C27 H27B S 0.96 2.99 3.746(4) 136.2 1_554
C3 H3A O1 0.97 2.51 3.321(3) 140.5 2_665
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 O11 1.5(3) . . . . ?
C16 C11 C12 O11 -176.4(2) . . . . ?
O1 C11 C12 C13 -179.2(2) . . . . ?
C16 C11 C12 C13 2.9(3) . . . . ?
O11 C12 C13 C14 177.7(3) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
O1 C11 C16 C15 -180.0(2) . . . . ?
C12 C11 C16 C15 -2.2(3) . . . . ?
O1 C11 C16 C1 -5.1(3) . . . . ?
C12 C11 C16 C1 172.7(2) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C14 C15 C16 C1 -174.8(2) . . . . ?
O2 C1 C16 C11 106.4(2) . . . . ?
N C1 C16 C11 -15.7(3) . . . . ?
O2 C1 C16 C15 -78.9(3) . . . . ?
N C1 C16 C15 159.1(2) . . . . ?
C16 C11 O1 C2 -10.2(3) . . . . ?
C12 C11 O1 C2 171.95(19) . . . . ?
C13 C12 O11 C17 -0.9(4) . . . . ?
C11 C12 O11 C17 178.3(2) . . . . ?
C11 O1 C2 N 47.8(2) . . . . ?
C11 O1 C2 C26 -74.2(2) . . . . ?
O2 C21 C22 O21 0.2(3) . . . . ?
C26 C21 C22 O21 -178.8(2) . . . . ?
O2 C21 C22 C23 -178.8(2) . . . . ?
C26 C21 C22 C23 2.3(4) . . . . ?
O21 C22 C23 C24 -179.1(3) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
O2 C21 C26 C25 178.3(2) . . . . ?
C22 C21 C26 C25 -2.8(3) . . . . ?
O2 C21 C26 C2 -4.2(3) . . . . ?
C22 C21 C26 C2 174.7(2) . . . . ?
C24 C25 C26 C21 1.4(4) . . . . ?
C24 C25 C26 C2 -176.2(2) . . . . ?
N C2 C26 C21 -17.7(3) . . . . ?
O1 C2 C26 C21 106.1(2) . . . . ?
N C2 C26 C25 159.9(2) . . . . ?
O1 C2 C26 C25 -76.3(3) . . . . ?
C26 C21 O2 C1 -12.4(3) . . . . ?
C22 C21 O2 C1 168.6(2) . . . . ?
N C1 O2 C21 50.3(2) . . . . ?
C16 C1 O2 C21 -73.2(2) . . . . ?
C23 C22 O21 C27 -1.6(5) . . . . ?
C21 C22 O21 C27 179.6(3) . . . . ?
N C3 C31 C32 103.8(3) . . . . ?
N C3 C31 S -77.6(2) . . . . ?
C3 C31 C32 C33 178.2(2) . . . . ?
S C31 C32 C33 -0.6(3) . . . . ?
C31 C32 C33 C34 -0.1(4) . . . . ?
C32 C33 C34 S 0.7(4) . . . . ?
C33 C34 S C31 -0.8(3) . . . . ?
C32 C31 S C34 0.8(2) . . . . ?
C3 C31 S C34 -178.0(2) . . . . ?
O1 C2 N C1 -68.6(2) . . . . ?
C26 C2 N C1 54.2(2) . . . . ?
O1 C2 N C3 57.7(2) . . . . ?
C26 C2 N C3 -179.43(18) . . . . ?
O2 C1 N C2 -73.7(2) . . . . ?
C16 C1 N C2 50.0(2) . . . . ?
O2 C1 N C3 160.86(18) . . . . ?
C16 C1 N C3 -75.4(2) . . . . ?
C31 C3 N C2 169.0(2) . . . . ?
C31 C3 N C1 -68.2(3) . . . . ?
