#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:30:39 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229113 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/06/7230650.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_7230650
loop_
_publ_author_name
'Pike, Sarah J.'
'Bond, Andrew D.'
'Hunter, Christopher A.'
_publ_section_title
;
 Solvatomorphism of Reichardt's dye
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              2912
_journal_paper_doi               10.1039/C8CE00480C
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C41 H29 N O, 1.4(C4 H10 O)'
_chemical_formula_sum            'C46.6 H43 N O2.4'
_chemical_formula_weight         655.45
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-10 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.2009(5)
_cell_length_b                   29.2009(5)
_cell_length_c                   23.3366(4)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.77
_cell_measurement_theta_min      3.03
_cell_volume                     17233.0(5)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.810
_diffrn_reflns_theta_max         66.810
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.53
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             6278.4
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0542P)²+8.8609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2578
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00480c2.cif
_cod_data_source_block           CCDC_1827191
_cod_depositor_comments
'Adding full bibliography for 7230640--7230651.cif.'
_cod_original_cell_volume        17233.0(7)
_cod_database_code               7230650
_cambridge_user_name             'Sarah Pike'
_cambridge_user_crsid            sp816
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             SP044
_cambridge_data_id               CH_B2_0026
_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   0.880
_shelx_estimated_absorpt_t_max   0.958
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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
O1 O 0.6667 0.94330(5) 0.5833 0.0468(4) Uani 1 2 d S T P
N1 N 0.6667 0.75265(6) 0.5833 0.0423(4) Uani 1 2 d S T P
C1 C 0.6667 0.89951(7) 0.5833 0.0390(4) Uani 1 2 d S T P
C2 C 0.63070(6) 0.85523(6) 0.61819(5) 0.0405(3) Uani 1 1 d . . .
C3 C 0.63178(6) 0.80869(6) 0.61814(5) 0.0442(3) Uani 1 1 d . . .
H3A H 0.6083 0.7805 0.6423 0.053 Uiso 1 1 calc R U .
C4 C 0.6667 0.80240(7) 0.5833 0.0450(5) Uani 1 2 d S T P
C5 C 0.67345(6) 0.73256(6) 0.63401(5) 0.0434(3) Uani 1 1 d . . .
C6 C 0.67041(6) 0.68407(6) 0.63408(5) 0.0438(3) Uani 1 1 d . . .
H6A H 0.6709 0.6684 0.6696 0.053 Uiso 1 1 calc R U .
C7 C 0.6667 0.65734(7) 0.5833 0.0416(4) Uani 1 2 d S T P
C8 C 0.6667 0.60681(7) 0.5833 0.0417(4) Uani 1 2 d S T P
C9 C 0.64619(7) 0.57222(6) 0.62981(6) 0.0485(4) Uani 1 1 d . . .
H9A H 0.6322 0.5812 0.6618 0.058 Uiso 1 1 calc R U .
C10 C 0.64628(7) 0.52491(7) 0.62928(6) 0.0568(4) Uani 1 1 d . . .
H10A H 0.6321 0.5015 0.6610 0.068 Uiso 1 1 calc R U .
C11 C 0.6667 0.51124(8) 0.5833 0.0582(6) Uani 1 2 d S T P
H11A H 0.6667 0.4787 0.5833 0.070 Uiso 1 2 calc R U P
C12 C 0.59029(6) 0.85805(6) 0.65462(6) 0.0450(3) Uani 1 1 d . . .
C13 C 0.54782(8) 0.85918(8) 0.63068(7) 0.0635(5) Uani 1 1 d . . .
H13A H 0.5464 0.8622 0.5903 0.076 Uiso 1 1 calc R U .
C14 C 0.50703(8) 0.85602(9) 0.66386(8) 0.0742(6) Uani 1 1 d . . .
H14A H 0.4777 0.8560 0.6462 0.089 Uiso 1 1 calc R U .
C15 C 0.50920(8) 0.85294(8) 0.72240(9) 0.0712(5) Uani 1 1 d . . .
H15A H 0.4810 0.8500 0.7455 0.085 Uiso 1 1 calc R U .
C16 C 0.55218(10) 0.85418(10) 0.74716(8) 0.0810(6) Uani 1 1 d . . .
H16A H 0.5546 0.8538 0.7877 0.097 Uiso 1 1 calc R U .
C17 C 0.59218(8) 0.85601(9) 0.71389(7) 0.0673(5) Uani 1 1 d . . .
H17A H 0.6213 0.8559 0.7318 0.081 Uiso 1 1 calc R U .
C18 C 0.68663(6) 0.76419(6) 0.68771(6) 0.0457(4) Uani 1 1 d . . .
C19 C 0.72803(8) 0.81605(7) 0.69024(7) 0.0606(4) Uani 1 1 d . . .
H19A H 0.7479 0.8326 0.6567 0.073 Uiso 1 1 calc R U .
C20 C 0.74050(9) 0.84374(8) 0.74132(7) 0.0715(5) Uani 1 1 d . . .
H20A H 0.7694 0.8790 0.7429 0.086 Uiso 1 1 calc R U .
C21 C 0.71114(9) 0.82033(8) 0.78992(7) 0.0684(5) Uani 1 1 d . . .
H21A H 0.7188 0.8398 0.8246 0.082 Uiso 1 1 calc R U .
C22 C 0.67085(9) 0.76891(7) 0.78796(6) 0.0634(5) Uani 1 1 d . . .
H22A H 0.6510 0.7527 0.8216 0.076 Uiso 1 1 calc R U .
C23 C 0.65875(7) 0.74017(6) 0.73735(6) 0.0516(4) Uani 1 1 d . . .
H23A H 0.6315 0.7042 0.7367 0.062 Uiso 1 1 calc R U .
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'
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
C5 N1 C5 120.30(16) . 18_655
C5 N1 C4 119.85(8) . .
C5 N1 C4 119.85(8) 18_655 .
O1 C1 C2 122.18(9) . .
O1 C1 C2 122.18(9) . 18_655
C2 C1 C2 115.64(17) . 18_655
C3 C2 C1 121.30(13) . .
C3 C2 C12 117.72(13) . .
C1 C2 C12 120.97(13) . .
C2 C3 C4 120.88(14) . .
C2 C3 H3A 119.6 . .
C4 C3 H3A 119.6 . .
C3 C4 C3 119.96(19) . 18_655
C3 C4 N1 120.02(9) . .
C3 C4 N1 120.02(9) 18_655 .
C6 C5 N1 119.41(12) . .
C6 C5 C18 120.12(12) . .
N1 C5 C18 120.40(13) . .
C5 C6 C7 121.56(13) . .
C5 C6 H6A 119.2 . .
C7 C6 H6A 119.2 . .
C6 C7 C6 117.15(18) . 18_655
C6 C7 C8 121.43(9) . .
C6 C7 C8 121.43(9) 18_655 .
C9 C8 C9 118.78(19) . 18_655
C9 C8 C7 120.60(10) . .
C9 C8 C7 120.61(10) 18_655 .
C10 C9 C8 120.10(14) . .
C10 C9 H9A 120.0 . .
C8 C9 H9A 120.0 . .
C11 C10 C9 120.87(15) . .
C11 C10 H10A 119.6 . .
C9 C10 H10A 119.6 . .
C10 C11 C10 119.3(2) 18_655 .
C10 C11 H11A 120.4 18_655 .
C10 C11 H11A 120.4 . .
C13 C12 C17 117.50(15) . .
C13 C12 C2 121.20(13) . .
C17 C12 C2 121.16(15) . .
C12 C13 C14 121.82(16) . .
C12 C13 H13A 119.1 . .
C14 C13 H13A 119.1 . .
C15 C14 C13 119.64(19) . .
C15 C14 H14A 120.2 . .
C13 C14 H14A 120.2 . .
C16 C15 C14 119.42(17) . .
C16 C15 H15A 120.3 . .
C14 C15 H15A 120.3 . .
C15 C16 C17 120.76(17) . .
C15 C16 H16A 119.6 . .
C17 C16 H16A 119.6 . .
C16 C17 C12 120.76(18) . .
C16 C17 H17A 119.6 . .
C12 C17 H17A 119.6 . .
C23 C18 C19 119.11(14) . .
C23 C18 C5 119.00(14) . .
C19 C18 C5 121.78(13) . .
C20 C19 C18 120.37(16) . .
C20 C19 H19A 119.8 . .
C18 C19 H19A 119.8 . .
C21 C20 C19 120.15(18) . .
C21 C20 H20A 119.9 . .
C19 C20 H20A 119.9 . .
C22 C21 C20 119.76(15) . .
C22 C21 H21A 120.1 . .
C20 C21 H21A 120.1 . .
C21 C22 C23 120.73(16) . .
C21 C22 H22A 119.6 . .
C23 C22 H22A 119.6 . .
C18 C23 C22 119.79(16) . .
C18 C23 H23A 120.1 . .
C22 C23 H23A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.279(2) .
N1 C5 1.3777(15) .
N1 C5 1.3779(15) 18_655
N1 C4 1.453(3) .
C1 C2 1.4416(17) .
C1 C2 1.4418(17) 18_655
C2 C3 1.375(2) .
C2 C12 1.490(2) .
C3 C4 1.3851(18) .
C3 H3A 0.9500 .
C4 C3 1.3852(18) 18_655
C5 C6 1.374(2) .
C5 C18 1.4886(19) .
C6 C7 1.3923(17) .
C6 H6A 0.9500 .
C7 C6 1.3923(17) 18_655
C7 C8 1.475(3) .
C8 C9 1.3965(18) .
C8 C9 1.3965(18) 18_655
C9 C10 1.383(2) .
C9 H9A 0.9500 .
C10 C11 1.379(2) .
C10 H10A 0.9500 .
C11 C10 1.379(2) 18_655
C11 H11A 0.9500 .
C12 C13 1.376(2) .
C12 C17 1.387(2) .
C13 C14 1.385(3) .
C13 H13A 0.9500 .
C14 C15 1.373(3) .
C14 H14A 0.9500 .
C15 C16 1.366(3) .
C15 H15A 0.9500 .
C16 C17 1.381(3) .
C16 H16A 0.9500 .
C17 H17A 0.9500 .
C18 C23 1.388(2) .
C18 C19 1.388(2) .
C19 C20 1.383(2) .
C19 H19A 0.9500 .
C20 C21 1.379(3) .
C20 H20A 0.9500 .
C21 C22 1.369(3) .
C21 H21A 0.9500 .
C22 C23 1.388(2) .
C22 H22A 0.9500 .
C23 H23A 0.9500 .
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_4
O1 C1 C2 C3 -179.15(10) . .
C2 C1 C2 C3 0.85(10) 18_655 .
O1 C1 C2 C12 2.12(14) . .
C2 C1 C2 C12 -177.87(14) 18_655 .
C1 C2 C3 C4 -1.72(19) . .
C12 C2 C3 C4 177.05(11) . .
C2 C3 C4 C3 0.87(10) . 18_655
C2 C3 C4 N1 -179.14(10) . .
C5 N1 C4 C3 -55.61(10) . .
C5 N1 C4 C3 124.39(10) 18_655 .
C5 N1 C4 C3 124.38(10) . 18_655
C5 N1 C4 C3 -55.61(10) 18_655 18_655
C5 N1 C5 C6 -3.66(10) 18_655 .
C4 N1 C5 C6 176.34(10) . .
C5 N1 C5 C18 173.28(16) 18_655 .
C4 N1 C5 C18 -6.72(16) . .
N1 C5 C6 C7 7.5(2) . .
C18 C5 C6 C7 -169.49(12) . .
C5 C6 C7 C6 -3.76(11) . 18_655
C5 C6 C7 C8 176.24(11) . .
C6 C7 C8 C9 30.09(11) . .
C6 C7 C8 C9 -149.91(11) 18_655 .
C6 C7 C8 C9 -149.91(11) . 18_655
C6 C7 C8 C9 30.10(11) 18_655 18_655
C9 C8 C9 C10 -0.16(12) 18_655 .
C7 C8 C9 C10 179.84(12) . .
C8 C9 C10 C11 0.3(2) . .
C9 C10 C11 C10 -0.16(12) . 18_655
C3 C2 C12 C13 -109.19(18) . .
C1 C2 C12 C13 69.58(19) . .
C3 C2 C12 C17 66.4(2) . .
C1 C2 C12 C17 -114.83(17) . .
C17 C12 C13 C14 -2.9(3) . .
C2 C12 C13 C14 172.89(18) . .
C12 C13 C14 C15 1.6(3) . .
C13 C14 C15 C16 1.4(3) . .
C14 C15 C16 C17 -3.0(4) . .
C15 C16 C17 C12 1.7(4) . .
C13 C12 C17 C16 1.2(3) . .
C2 C12 C17 C16 -174.54(19) . .
C6 C5 C18 C23 -50.2(2) . .
N1 C5 C18 C23 132.91(14) . .
C6 C5 C18 C19 125.99(17) . .
N1 C5 C18 C19 -50.9(2) . .
C23 C18 C19 C20 -1.4(3) . .
C5 C18 C19 C20 -177.61(17) . .
C18 C19 C20 C21 -1.3(3) . .
C19 C20 C21 C22 2.5(3) . .
C20 C21 C22 C23 -0.8(3) . .
C19 C18 C23 C22 3.1(3) . .
C5 C18 C23 C22 179.38(15) . .
C21 C22 C23 C18 -2.0(3) . .
