Conserved hydrogen bonding in tetrahydrocarbazolone derivatives: influence of solution-state assembly on crystal form nucleation
Robert M. Edkins; Elliott Hayden; Jonathan W. Steed; Katharina Fucke; Chem.Commun. 51 (2015) 5314–; doi:10.1039/C4cc10453F

data_7116787
_publ_section_title
;
 Conserved hydrogen bonding in tetrahydrocarbazolone derivatives:
 influence of solution-state assembly on crystal form nucleation
;
_journal_name_full               Chem.Commun.
_journal_page_first              5314
_journal_paper_doi               10.1039/C4cc10453F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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'
_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_date             2014-11-22
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-12-23 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.103(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4905(5)
_cell_length_b                   4.9370(2)
_cell_length_c                   21.8359(11)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6343
_cell_measurement_theta_min      2.7209
_cell_volume                     1019.06(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details
;
  1 omega  -42.00   42.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   38.0000 -150.0000 84

  2 omega  -90.00   21.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -17.0000   14.0000 111

  3 omega  -23.00    5.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -38.0000  120.0000 28

  4 omega   30.00   75.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -113.0000 -178.0000 45

  5 omega   59.00   84.00   1.0000  113.2700
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0602767000
_diffrn_orient_matrix_UB_12      -0.0053695000
_diffrn_orient_matrix_UB_13      0.0216281000
_diffrn_orient_matrix_UB_21      0.0440003000
_diffrn_orient_matrix_UB_22      0.0323078000
_diffrn_orient_matrix_UB_23      -0.0235788000
_diffrn_orient_matrix_UB_31      -0.0078177000
_diffrn_orient_matrix_UB_32      0.1399109000
_diffrn_orient_matrix_UB_33      0.0062815000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6965
_diffrn_reflns_theta_full        32.71
_diffrn_reflns_theta_max         32.71
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.6185
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.0395
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0860
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2088
_reflns_number_gt                2125
_reflns_number_total             3335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10453f2.cif
_cod_data_source_block           ocb_ii_2
_cod_original_cell_volume        1019.05(9)
_cod_database_code               7116787
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.018) H8(0.022) H5A(0.021) H5B(0.021) H13A(0.032) H13B(0.032)
 H13C(0.032) H10(0.026) H3A(0.027) H3B(0.027) H9(0.025) H4A(0.027) H4B(0.027)
 Fixed X: H1(0.1408) H8(0.3257) H5A(0.0439) H5B(0.0263) H13A(0.3577)
 H13B(0.5168) H13C(0.3923) H10(0.5818) H3A(-0.2712) H3B(-0.1458) H9(0.5425)
 H4A(-0.1982) H4B(-0.1802)
 Fixed Y: H1(0.9924) H8(0.4715) H5A(0.1785) H5B(0.3822) H13A(1.3861)
 H13B(1.2827) H13C(1.1584) H10(1.0299) H3A(0.4608) H3B(0.2509) H9(0.6935)
 H4A(0.2421) H4B(0.5636)
 Fixed Z: H1(0.4585) H8(0.2769) H5A(0.3294) H5B(0.272) H13A(0.4374)
 H13B(0.4526) H13C(0.4887) H10(0.3657) H3A(0.3973) H3B(0.4148) H9(0.2909)
 H4A(0.3081) H4B(0.3038)
;
_olex2_date_sample_data_collection 1302517750.72
_olex2_exptl_crystal_mounting_method 'on loop'
_olex2_submission_special_instructions 'No special instructions were received'