#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/26/2222695.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_2222695
loop_
_publ_author_name
'Rodriguez, Mark A.'
'O'Bryan, Greg'
'Andrzejewski, William J.'
'McElhanon, James R.'
_publ_section_title
;2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate
 dihydrate
;
_journal_coeditor_code           GK2221
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1906
_journal_page_last               o1907
_journal_paper_doi               10.1107/S1600536809027238
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H22 N2 O5, 2H2 O'
_chemical_formula_moiety         'C21 H22 N2 O5, 2(H2 O)'
_chemical_formula_sum            'C21 H26 N2 O7'
_chemical_formula_weight         418.44
_chemical_name_systematic
;
2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-
yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.603(5)
_cell_angle_beta                 101.639(6)
_cell_angle_gamma                102.140(7)
_cell_formula_units_Z            2
_cell_length_a                   7.377(2)
_cell_length_b                   8.868(2)
_cell_length_c                   16.817(5)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1044.8(5)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics
;
XSHELL (Bruker, 2000) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'XSHELL (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7525
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1999)
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      1.31(8)
_exptl_crystal_density_method    picnometer
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0540
_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)+(0.0611P)²+0.0096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                2472
_reflns_number_total             3651
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2221.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222695
_cod_database_fobs_code          2222695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N N1 0.4314(3) 0.7565(2) 0.27176(12) 0.0266(5) Uani d . 1 . .
N N2 -0.7317(3) 0.3125(2) 0.07265(13) 0.0297(5) Uani d . 1 . .
O O1 0.3009(3) 0.8842(2) 0.40555(12) 0.0453(5) Uani d . 1 . .
H H1 0.3172 0.9730 0.3903 0.054 Uiso d R 1 . .
O O2 -0.1195(2) 0.4576(2) 0.33751(11) 0.0348(5) Uani d . 1 . .
O O3 -0.7048(3) 0.3290(2) 0.00334(11) 0.0399(5) Uani d . 1 . .
O O4 -0.8914(3) 0.2639(2) 0.08513(12) 0.0439(6) Uani d . 1 . .
O O5 -0.6302(2) 0.1775(2) 0.36144(11) 0.0376(5) Uani d . 1 . .
H H5 -0.7015 0.2285 0.3787 0.045 Uiso d R 1 . .
C C1 0.5663(3) 0.8684(3) 0.24386(15) 0.0275(6) Uani d . 1 . .
C C2 0.7509(4) 0.9396(3) 0.28370(17) 0.0337(7) Uani d . 1 . .
H H2A 0.8074 0.9150 0.3355 0.040 Uiso d R 1 . .
C C3 0.8489(4) 1.0488(3) 0.24380(18) 0.0392(7) Uani d . 1 . .
H H3 0.9755 1.1027 0.2694 0.047 Uiso d R 1 . .
C C4 0.7670(4) 1.0812(3) 0.16759(18) 0.0381(7) Uani d . 1 . .
H H4 0.8380 1.1564 0.1416 0.046 Uiso d R 1 . .
C C5 0.5822(4) 1.0052(3) 0.12871(17) 0.0331(7) Uani d . 1 . .
H H5A 0.5267 1.0267 0.0760 0.040 Uiso d R 1 . .
C C6 0.4804(3) 0.8976(3) 0.16797(15) 0.0251(6) Uani d . 1 . .
C C7 0.2797(3) 0.8003(3) 0.14308(14) 0.0248(6) Uani d . 1 . .
C C8 0.2563(4) 0.6884(3) 0.06505(15) 0.0308(6) Uani d . 1 . .
H H8A 0.2692 0.7482 0.0192 0.046 Uiso d R 1 . .
H H8B 0.1302 0.6172 0.0529 0.046 Uiso d R 1 . .
H H8C 0.3545 0.6285 0.0734 0.046 Uiso d R 1 . .
C C9 0.1368(4) 0.9048(3) 0.12986(17) 0.0355(7) Uani d . 1 . .
H H9A 0.1498 0.9716 0.1810 0.053 Uiso d R 1 . .
H H9B 0.0071 0.8398 0.1132 0.053 Uiso d R 1 . .
H H9C 0.1625 0.9697 0.0871 0.053 Uiso d R 1 . .
C C10 0.2648(3) 0.7159(3) 0.21803(15) 0.0246(6) Uani d . 1 . .
C C11 0.4762(4) 0.7097(3) 0.35407(15) 0.0311(6) Uani d . 1 . .
H H11A 0.6030 0.6851 0.3639 0.037 Uiso d R 1 . .
H H11B 0.3813 0.6147 0.3575 0.037 Uiso d R 1 . .
C C12 0.4755(4) 0.8380(3) 0.41955(16) 0.0392(7) Uani d . 1 . .
H H12A 0.4980 0.8006 0.4738 0.047 Uiso d R 1 . .
H H12B 0.5804 0.9288 0.4203 0.047 Uiso d R 1 . .
C C13 0.1035(3) 0.6165(3) 0.23467(15) 0.0274(6) Uani d . 1 . .
H H13 0.1166 0.5811 0.2869 0.033 Uiso d R 1 . .
C C14 -0.0685(3) 0.5680(3) 0.18168(16) 0.0275(6) Uani d . 1 . .
H H14 -0.0760 0.5985 0.1284 0.033 Uiso d R 1 . .
C C15 -0.2409(3) 0.4756(3) 0.19654(15) 0.0244(6) Uani d . 1 . .
C C16 -0.3992(3) 0.4350(3) 0.13128(15) 0.0249(6) Uani d . 1 . .
H H16 -0.3883 0.4651 0.0792 0.030 Uiso d R 1 . .
C C17 -0.5708(3) 0.3522(3) 0.14124(15) 0.0249(6) Uani d . 1 . .
C C18 -0.5931(3) 0.3052(3) 0.21741(15) 0.0252(6) Uani d . 1 . .
H H18 -0.7142 0.2517 0.2237 0.030 Uiso d R 1 . .
C C19 -0.4402(4) 0.3369(3) 0.28191(15) 0.0250(6) Uani d . 1 . .
C C20 -0.2575(4) 0.4255(3) 0.27503(15) 0.0266(6) Uani d . 1 . .
C C21 -0.4511(4) 0.2795(3) 0.36328(16) 0.0327(7) Uani d . 1 . .
H H21A -0.3487 0.2240 0.3791 0.039 Uiso d R 1 . .
H H21B -0.4292 0.3699 0.4054 0.039 Uiso d R 1 . .
O O10 0.9517(3) 0.7347(2) 0.43717(12) 0.0471(6) Uani d . 1 . .
H H10A 1.0729 0.7979 0.4350 0.071 Uiso d R 1 . .
H H10B 0.9319 0.6349 0.4070 0.071 Uiso d R 1 . .
O O20 0.1635(3) 0.3445(3) 0.42365(13) 0.0642(7) Uani d . 1 . .
H H20B 0.1048 0.3071 0.4659 0.096 Uiso d R 1 . .
H H20A 0.0628 0.3721 0.3872 0.096 Uiso d 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
C10 N1 C1 . . 111.6(2) ?
C10 N1 C11 . . 127.0(2) ?
C1 N1 C11 . . 121.1(2) ?
O4 N2 O3 . . 122.4(2) ?
O4 N2 C17 . . 118.9(2) ?
O3 N2 C17 . . 118.8(2) ?
C12 O1 H1 . . 109.4 ?
C21 O5 H5 . . 109.4 ?
C6 C1 C2 . . 123.8(2) ?
C6 C1 N1 . . 108.1(2) ?
C2 C1 N1 . . 128.0(2) ?
C1 C2 C3 . . 116.1(3) ?
C1 C2 H2A . . 121.9 ?
C3 C2 H2A . . 122.0 ?
C4 C3 C2 . . 121.5(3) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 118.8(3) ?
C6 C5 H5A . . 120.6 ?
C4 C5 H5A . . 120.6 ?
C1 C6 C5 . . 119.0(2) ?
C1 C6 C7 . . 109.7(2) ?
C5 C6 C7 . . 131.3(2) ?
C6 C7 C10 . . 101.47(19) ?
C6 C7 C8 . . 110.0(2) ?
C10 C7 C8 . . 112.7(2) ?
C6 C7 C9 . . 110.5(2) ?
C10 C7 C9 . . 111.1(2) ?
C8 C7 C9 . . 110.8(2) ?
C7 C8 H8A . . 109.4 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.4 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.4 ?
H9B C9 H9C . . 109.5 ?
N1 C10 C13 . . 122.2(2) ?
N1 C10 C7 . . 109.0(2) ?
C13 C10 C7 . . 128.7(2) ?
N1 C11 C12 . . 111.2(2) ?
N1 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
N1 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
O1 C12 C11 . . 111.7(2) ?
O1 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.3 ?
O1 C12 H12B . . 109.3 ?
C11 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C10 . . 125.0(2) ?
C14 C13 H13 . . 117.5 ?
C10 C13 H13 . . 117.5 ?
C13 C14 C15 . . 127.7(2) ?
C13 C14 H14 . . 116.1 ?
C15 C14 H14 . . 116.2 ?
C16 C15 C14 . . 117.3(2) ?
C16 C15 C20 . . 119.2(2) ?
C14 C15 C20 . . 123.5(2) ?
C17 C16 C15 . . 120.9(2) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.6 ?
C16 C17 C18 . . 121.4(2) ?
C16 C17 N2 . . 119.5(2) ?
C18 C17 N2 . . 119.1(2) ?
C19 C18 C17 . . 119.7(2) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C18 C19 C20 . . 121.1(2) ?
C18 C19 C21 . . 122.3(2) ?
C20 C19 C21 . . 116.6(2) ?
O2 C20 C19 . . 119.4(2) ?
O2 C20 C15 . . 122.9(2) ?
C19 C20 C15 . . 117.7(2) ?
O5 C21 C19 . . 112.6(2) ?
O5 C21 H21A . . 109.0 ?
C19 C21 H21A . . 109.1 ?
O5 C21 H21B . . 109.1 ?
C19 C21 H21B . . 109.1 ?
H21A C21 H21B . . 107.8 ?
H10A O10 H10B . . 110.1 ?
H20B O20 H20A . . 102.9 ?
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
N1 C10 . 1.331(3) ?
N1 C1 . 1.429(3) ?
N1 C11 . 1.471(3) ?
N2 O4 . 1.232(3) ?
N2 O3 . 1.236(3) ?
N2 C17 . 1.439(3) ?
O1 C12 . 1.414(3) ?
O1 H1 . 0.8400 ?
O2 C20 . 1.273(3) ?
O5 C21 . 1.429(3) ?
O5 H5 . 0.8405 ?
C1 C6 . 1.376(3) ?
C1 C2 . 1.380(3) ?
C2 C3 . 1.385(4) ?
C2 H2A . 0.9507 ?
C3 C4 . 1.382(4) ?
C3 H3 . 0.9503 ?
C4 C5 . 1.387(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.382(3) ?
C5 H5A . 0.9502 ?
C6 C7 . 1.506(3) ?
C7 C10 . 1.527(3) ?
C7 C8 . 1.538(3) ?
C7 C9 . 1.539(3) ?
C8 H8A . 0.9795 ?
C8 H8B . 0.9805 ?
C8 H8C . 0.9795 ?
C9 H9A . 0.9797 ?
C9 H9B . 0.9799 ?
C9 H9C . 0.9803 ?
C10 C13 . 1.416(3) ?
C11 C12 . 1.520(4) ?
C11 H11A . 0.9895 ?
C11 H11B . 0.9895 ?
C12 H12A . 0.9904 ?
C12 H12B . 0.9898 ?
C13 C14 . 1.357(3) ?
C13 H13 . 0.9492 ?
C14 C15 . 1.440(3) ?
C14 H14 . 0.9503 ?
C15 C16 . 1.393(3) ?
C15 C20 . 1.446(3) ?
C16 C17 . 1.373(3) ?
C16 H16 . 0.9504 ?
C17 C18 . 1.408(3) ?
C18 C19 . 1.361(3) ?
C18 H18 . 0.9499 ?
C19 C20 . 1.442(3) ?
C19 C21 . 1.509(3) ?
C21 H21A . 0.9901 ?
C21 H21B . 0.9898 ?
O10 H10A . 0.9594 ?
O10 H10B . 0.9515 ?
O20 H20B . 0.9502 ?
O20 H20A . 0.9513 ?
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
O20 H20B O10 2_666 0.96 1.80 2.739(4) 166
O10 H10B O2 1_655 0.95 1.81 2.750(3) 172
O20 H20A O2 . 0.95 1.78 2.714(3) 167
O10 H10A O1 1_655 0.95 1.87 2.811(3) 165
O5 H5 O20 1_455 0.84 1.80 2.633(3) 175
O1 H1 O5 1_665 0.84 1.90 2.734(3) 176
