#------------------------------------------------------------------------------
#$Date: 2020-03-27 05:51:20 +0200 (Fri, 27 Mar 2020) $
#$Revision: 249770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240211.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_7240211
loop_
_publ_author_name
'Mazzeo, Paolo Pio'
'Canossa, Stefano'
'Carraro, Claudia'
'Pelagatti, Paolo'
'Bacchi, Alessia'
_publ_section_title
;
 Systematic coformer contribution to cocrystal stabilization: energy and
 packing trends
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00291G
_journal_year                    2020
_chemical_formula_moiety         'C10 H14 O, C13 H9 N'
_chemical_formula_sum            'C23 H23 N O'
_chemical_formula_weight         329.42
_chemical_name_systematic        'Acridine 5-Methyl-2-(propan-2-yl)phenol'
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-26 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.13720(10)
_cell_length_b                   9.12090(10)
_cell_length_c                   17.2439(2)
_cell_measurement_reflns_used    23232
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.0890
_cell_measurement_theta_min      1.7420
_cell_volume                     1808.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 360.00   0.30    1.00   0.00   0.00   0.00    --  1200
;
_diffrn_measurement_device       'Huber 4-circles Kappa Goniometer'
_diffrn_measurement_device_type  '4-circles Kappa Goniometer'
_diffrn_measurement_method       'Rotation around the Phi axis'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29477
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         28.642
_diffrn_reflns_theta_min         1.744
_diffrn_source                   synchrotron
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_preparation       'Grinding reaction'
_exptl_crystal_recrystallization_method 'Slow solvent evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.118(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0617
_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)+(0.1123P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4525
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00291g2.cif
_cod_data_source_block           tiac1_2_
_cod_database_code               7240211
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.25836(6) 0.68455(8) 0.63694(5) 0.0276(2) Uani 1 1 d . . . . .
N1 N 0.17122(7) 0.51627(9) 0.49502(5) 0.0215(2) Uani 1 1 d . . . . .
C18 C 0.00511(7) 0.47117(10) 0.37306(6) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.42990(8) 0.76152(11) 0.60607(6) 0.0245(2) Uani 1 1 d . . . . .
C17 C 0.01117(8) 0.32157(10) 0.39049(6) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.35976(7) 0.76218(10) 0.65626(5) 0.0201(2) Uani 1 1 d . . . . .
C6 C 0.39071(7) 0.84389(10) 0.72888(5) 0.0195(2) Uani 1 1 d . . . . .
C5 C 0.49140(8) 0.92813(11) 0.74675(6) 0.0243(2) Uani 1 1 d . . . . .
C23 C 0.08837(8) 0.56589(10) 0.42787(6) 0.0203(2) Uani 1 1 d . . . . .
C11 C 0.17707(7) 0.37079(10) 0.51015(6) 0.0203(2) Uani 1 1 d . . . . .
C8 C 0.31496(8) 0.84468(11) 0.78385(6) 0.0222(2) Uani 1 1 d . . . . .
C19 C -0.07924(8) 0.53206(11) 0.30276(6) 0.0255(2) Uani 1 1 d . . . . .
C16 C 0.09760(8) 0.26808(10) 0.45862(6) 0.0203(2) Uani 1 1 d . . . . .
C4 C 0.56145(8) 0.92854(12) 0.69670(7) 0.0288(2) Uani 1 1 d . . . . .
C12 C 0.26662(9) 0.31679(12) 0.57958(6) 0.0260(2) Uani 1 1 d . . . . .
C3 C 0.53165(8) 0.84416(13) 0.62594(6) 0.0281(2) Uani 1 1 d . . . . .
C22 C 0.08472(9) 0.71875(10) 0.40944(6) 0.0263(2) Uani 1 1 d . . . . .
C20 C -0.07943(9) 0.67824(12) 0.28677(7) 0.0294(2) Uani 1 1 d . . . . .
C15 C 0.10991(9) 0.11578(10) 0.47892(6) 0.0253(2) Uani 1 1 d . . . . .
C13 C 0.27714(9) 0.17040(12) 0.59614(7) 0.0291(2) Uani 1 1 d . . . . .
C21 C 0.00383(10) 0.77201(11) 0.34078(7) 0.0294(2) Uani 1 1 d . . . . .
C14 C 0.19745(9) 0.06883(11) 0.54567(7) 0.0289(2) Uani 1 1 d . . . . .
C10 C 0.23595(12) 0.97820(16) 0.76676(9) 0.0419(3) Uani 1 1 d . . . . .
C9 C 0.38518(10) 0.83476(18) 0.87421(7) 0.0402(3) Uani 1 1 d . . . . .
C7 C 0.60746(11) 0.8424(2) 0.57156(8) 0.0426(3) Uani 1 1 d . . . . .
H2 H 0.4028(14) 0.7025(19) 0.5540(11) 0.041(4) Uiso 1 1 d . . . . .
H5 H 0.5133(13) 0.9908(17) 0.7951(9) 0.031(3) Uiso 1 1 d . . . . .
H20 H -0.1362(14) 0.7180(19) 0.2379(10) 0.041(4) Uiso 1 1 d . . . . .
H12 H 0.3199(14) 0.3864(18) 0.6128(10) 0.039(4) Uiso 1 1 d . . . . .
H17 H -0.0462(12) 0.2534(16) 0.3538(8) 0.027(3) Uiso 1 1 d . . . . .
H8 H 0.2627(12) 0.7556(17) 0.7689(9) 0.030(3) Uiso 1 1 d . . . . .
H22 H 0.1418(13) 0.7834(18) 0.4492(10) 0.036(4) Uiso 1 1 d . . . . .
H13 H 0.3413(14) 0.1385(19) 0.6438(10) 0.037(4) Uiso 1 1 d . . . . .
H4 H 0.6361(16) 0.988(2) 0.7130(11) 0.048(4) Uiso 1 1 d . . . . .
H19 H -0.1357(14) 0.4639(19) 0.2674(10) 0.040(4) Uiso 1 1 d . . . . .
H15 H 0.0531(14) 0.0449(18) 0.4424(10) 0.034(4) Uiso 1 1 d . . . . .
H10A H 0.1806(18) 0.979(2) 0.8005(13) 0.061(5) Uiso 1 1 d . . . . .
H14 H 0.2077(14) -0.0349(19) 0.5608(10) 0.040(4) Uiso 1 1 d . . . . .
H9A H 0.3302(14) 0.831(2) 0.9094(11) 0.045(4) Uiso 1 1 d . . . . .
H9B H 0.4395(17) 0.744(2) 0.8863(13) 0.061(5) Uiso 1 1 d . . . . .
H9C H 0.4304(17) 0.925(2) 0.8925(12) 0.056(5) Uiso 1 1 d . . . . .
H10B H 0.2800(17) 1.070(2) 0.7764(12) 0.056(5) Uiso 1 1 d . . . . .
H10C H 0.1886(17) 0.987(2) 0.7073(12) 0.054(5) Uiso 1 1 d . . . . .
H21 H 0.0039(14) 0.874(2) 0.3282(10) 0.043(4) Uiso 1 1 d . . . . .
H7A H 0.623(2) 0.743(3) 0.5592(15) 0.086(8) Uiso 1 1 d . . . . .
H1 H 0.2409(18) 0.634(2) 0.5864(13) 0.066(6) Uiso 1 1 d . . . . .
H7B H 0.684(2) 0.882(3) 0.6004(17) 0.093(8) Uiso 1 1 d . . . . .
H7C H 0.568(2) 0.885(3) 0.5212(15) 0.079(7) Uiso 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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113.2(13) . . ?
C23 N1 C11 118.39(8) . . ?
C17 C18 C23 118.08(8) . . ?
C17 C18 C19 122.58(8) . . ?
C19 C18 C23 119.33(8) . . ?
C1 C2 H2 117.7(10) . . ?
C3 C2 C1 120.94(9) . . ?
C3 C2 H2 121.3(10) . . ?
C18 C17 H17 119.7(8) . . ?
C16 C17 C18 119.96(8) . . ?
C16 C17 H17 120.3(8) . . ?
O1 C1 C2 121.85(8) . . ?
O1 C1 C6 117.20(8) . . ?
C2 C1 C6 120.95(8) . . ?
C1 C6 C8 121.19(8) . . ?
C5 C6 C1 117.19(8) . . ?
C5 C6 C8 121.57(8) . . ?
C6 C5 H5 119.6(9) . . ?
C4 C5 C6 122.09(9) . . ?
C4 C5 H5 118.3(9) . . ?
N1 C23 C18 122.72(8) . . ?
N1 C23 C22 118.77(8) . . ?
C22 C23 C18 118.50(9) . . ?
N1 C11 C16 122.67(8) . . ?
N1 C11 C12 118.79(8) . . ?
C12 C11 C16 118.53(8) . . ?
C6 C8 C10 110.71(8) . . ?
C6 C8 C9 112.75(8) . . ?
C6 C8 H8 107.0(8) . . ?
C10 C8 C9 111.02(10) . . ?
C10 C8 H8 106.8(8) . . ?
C9 C8 H8 108.3(8) . . ?
C18 C19 H19 116.8(10) . . ?
C20 C19 C18 120.52(9) . . ?
C20 C19 H19 122.7(10) . . ?
C17 C16 C11 118.16(8) . . ?
C17 C16 C15 122.69(8) . . ?
C15 C16 C11 119.15(9) . . ?
C5 C4 H4 119.8(11) . . ?
C3 C4 C5 120.27(9) . . ?
C3 C4 H4 119.9(11) . . ?
C11 C12 H12 117.6(10) . . ?
C13 C12 C11 120.70(10) . . ?
C13 C12 H12 121.7(10) . . ?
C2 C3 C7 120.68(10) . . ?
C4 C3 C2 118.51(9) . . ?
C4 C3 C7 120.81(10) . . ?
C23 C22 H22 117.4(9) . . ?
C21 C22 C23 120.25(9) . . ?
C21 C22 H22 122.4(9) . . ?
C19 C20 C21 120.13(10) . . ?
C19 C20 H20 119.7(10) . . ?
C21 C20 H20 120.1(10) . . ?
C16 C15 H15 118.3(9) . . ?
C14 C15 C16 120.33(9) . . ?
C14 C15 H15 121.3(9) . . ?
C12 C13 C14 120.75(10) . . ?
C12 C13 H13 117.6(10) . . ?
C14 C13 H13 121.6(10) . . ?
C22 C21 C20 121.25(9) . . ?
C22 C21 H21 119.4(10) . . ?
C20 C21 H21 119.3(10) . . ?
C15 C14 C13 120.52(9) . . ?
C15 C14 H14 121.9(10) . . ?
C13 C14 H14 117.6(10) . . ?
C8 C10 H10A 112.5(12) . . ?
C8 C10 H10B 112.0(12) . . ?
C8 C10 H10C 112.3(11) . . ?
H10A C10 H10B 109.0(16) . . ?
H10A C10 H10C 108.3(16) . . ?
H10B C10 H10C 102.2(16) . . ?
C8 C9 H9A 110.3(10) . . ?
C8 C9 H9B 111.4(12) . . ?
C8 C9 H9C 110.5(12) . . ?
H9A C9 H9B 110.3(15) . . ?
H9A C9 H9C 103.5(15) . . ?
H9B C9 H9C 110.6(15) . . ?
C3 C7 H7A 110.3(15) . . ?
C3 C7 H7B 110.4(16) . . ?
C3 C7 H7C 110.1(15) . . ?
H7A C7 H7B 104(2) . . ?
H7A C7 H7C 105(2) . . ?
H7B C7 H7C 116(2) . . ?
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
O1 C1 1.3656(11) . ?
O1 H1 0.95(2) . ?
N1 C23 1.3465(12) . ?
N1 C11 1.3498(12) . ?
C18 C17 1.3941(12) . ?
C18 C23 1.4320(12) . ?
C18 C19 1.4260(13) . ?
C2 C1 1.3944(12) . ?
C2 C3 1.3930(14) . ?
C2 H2 1.008(18) . ?
C17 C16 1.3897(13) . ?
C17 H17 0.995(14) . ?
C1 C6 1.4015(12) . ?
C6 C5 1.3923(12) . ?
C6 C8 1.5167(12) . ?
C5 C4 1.3914(14) . ?
C5 H5 0.975(15) . ?
C23 C22 1.4275(12) . ?
C11 C16 1.4317(12) . ?
C11 C12 1.4234(13) . ?
C8 C10 1.5195(15) . ?
C8 C9 1.5212(14) . ?
C8 H8 1.012(15) . ?
C19 C20 1.3613(14) . ?
C19 H19 0.980(17) . ?
C16 C15 1.4287(12) . ?
C4 C3 1.3893(15) . ?
C4 H4 1.015(18) . ?
C12 C13 1.3628(14) . ?
C12 H12 0.955(17) . ?
C3 C7 1.5091(14) . ?
C22 C21 1.3635(15) . ?
C22 H22 0.997(16) . ?
C20 C21 1.4209(16) . ?
C20 H20 0.972(17) . ?
C15 C14 1.3623(14) . ?
C15 H15 1.006(16) . ?
C13 C14 1.4190(16) . ?
C13 H13 0.978(16) . ?
C21 H21 0.960(18) . ?
C14 H14 0.979(17) . ?
C10 H10A 1.02(2) . ?
C10 H10B 0.98(2) . ?
C10 H10C 1.01(2) . ?
C9 H9A 1.036(17) . ?
C9 H9B 1.04(2) . ?
C9 H9C 0.99(2) . ?
C7 H7A 0.97(3) . ?
C7 H7B 0.97(3) . ?
C7 H7C 0.93(2) . ?
