#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558212.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_1558212
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18 H15.5 N2 O2'
_chemical_formula_weight         291.88
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-01T11:36:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.6153(16)
_cell_angle_beta                 107.5529(11)
_cell_angle_gamma                114.4384(13)
_cell_formula_units_Z            2
_cell_length_a                   8.11309(11)
_cell_length_b                   9.87420(17)
_cell_length_c                   10.89995(12)
_cell_measurement_reflns_used    18922
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      76.927
_cell_measurement_theta_min      4.327
_cell_volume                     743.20(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0955597
_diffrn_orient_matrix_UB_12      0.1047479
_diffrn_orient_matrix_UB_13      -0.1136285
_diffrn_orient_matrix_UB_21      0.1436057
_diffrn_orient_matrix_UB_22      0.0788873
_diffrn_orient_matrix_UB_23      -0.0450764
_diffrn_orient_matrix_UB_31      0.1244702
_diffrn_orient_matrix_UB_32      -0.115497
_diffrn_orient_matrix_UB_33      -0.088941
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.363
_diffrn_reflns_theta_min         4.339
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0
_reflns_number_gt                2835
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_210
_cod_original_formula_sum        'C18 H15.50 N2 O2'
_cod_database_code               1558212
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.956
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_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
O1 O 0.16661(10) 0.15384(8) 0.30489(7) 0.04282(19) Uani 1 1 d . . . . .
H1 H 0.199111 0.179311 0.385437 0.064 Uiso 1 1 calc R U . . .
O2 O 0.82265(10) 0.22591(9) 0.43212(7) 0.0492(2) Uani 1 1 d . . . . .
H2A H 0.827278 0.262645 0.503818 0.074 Uiso 1 1 calc R U . . .
N1 N 0.26212(12) 0.24546(11) -0.43138(8) 0.0438(2) Uani 1 1 d . . . . .
C1 C 0.31725(14) 0.15155(10) 0.27636(9) 0.0350(2) Uani 1 1 d . . . . .
C2 C 0.49417(14) 0.18887(10) 0.37328(9) 0.0355(2) Uani 1 1 d . . . . .
H2 H 0.511355 0.215548 0.461727 0.043 Uiso 1 1 calc R U . . .
C3 C 0.64660(14) 0.18712(11) 0.34047(9) 0.0376(2) Uani 1 1 d . . . . .
C4 C 0.62028(16) 0.14484(11) 0.20925(10) 0.0434(2) Uani 1 1 d . . . . .
H4 H 0.721573 0.142021 0.186066 0.052 Uiso 1 1 calc R U . . .
C5 C 0.44281(17) 0.10728(12) 0.11429(9) 0.0456(3) Uani 1 1 d . . . . .
H5 H 0.424761 0.079204 0.02589 0.055 Uiso 1 1 calc R U . . .
C6 C 0.29064(15) 0.10975(11) 0.14546(9) 0.0418(2) Uani 1 1 d . . . . .
H6 H 0.170985 0.08358 0.079161 0.05 Uiso 1 1 calc R U . . .
C7 C 0.19667(15) 0.14684(12) -0.35762(10) 0.0434(2) Uani 1 1 d . . . . .
H7 H 0.15576 0.043504 -0.388 0.052 Uiso 1 1 calc R U . . .
C8 C 0.18602(15) 0.18907(11) -0.23872(10) 0.0408(2) Uani 1 1 d . . . . .
H8 H 0.137705 0.115235 -0.190536 0.049 Uiso 1 1 calc R U . . .
C9 C 0.24699(13) 0.34103(11) -0.19069(9) 0.0364(2) Uani 1 1 d D U . . .
C10 C 0.32118(15) 0.44476(12) -0.26546(10) 0.0422(2) Uani 1 1 d . . . . .
H10 H 0.368585 0.549261 -0.235713 0.051 Uiso 1 1 calc R U . . .
C11 C 0.32419(15) 0.39222(12) -0.38365(10) 0.0446(2) Uani 1 1 d . . . . .
H11 H 0.372633 0.463539 -0.43371 0.053 Uiso 1 1 calc R U . . .
C12A C 0.2180(8) 0.3773(4) -0.0660(4) 0.0324(6) Uani 0.705(8) 1 d D U P A 1
H12A H 0.163265 0.297515 -0.024707 0.039 Uiso 0.705(8) 1 calc R U P A 1
C13A C 0.2674(4) 0.5195(3) -0.0112(2) 0.0305(5) Uani 0.705(8) 1 d D U P A 1
H13A H 0.326203 0.598395 -0.051963 0.037 Uiso 0.705(8) 1 calc R U P A 1
C12B C 0.269(7) 0.438(3) -0.082(3) 0.036(4) Uani 0.047(8) 1 d D U P A 2
H12B H 0.356354 0.537434 -0.080624 0.043 Uiso 0.047(8) 1 calc R U P A 2
C13B C 0.214(6) 0.439(3) 0.014(3) 0.039(3) Uani 0.047(8) 1 d D U P A 2
H13B H 0.144011 0.337329 0.019331 0.047 Uiso 0.047(8) 1 calc R U P A 2
C14A C 0.2354(8) 0.5610(4) 0.1102(4) 0.0311(7) Uani 0.705(8) 1 d DG U P A 1
C15A C 0.1491(8) 0.4533(3) 0.1779(4) 0.0349(7) Uani 0.705(8) 1 d G U P A 1
H15A H 0.111754 0.350288 0.148986 0.042 Uiso 0.705(8) 1 calc R U P A 1
C16A C 0.1182(8) 0.4979(4) 0.2883(4) 0.0353(8) Uani 0.705(8) 1 d G U P A 1
H16A H 0.05985 0.425098 0.334116 0.042 Uiso 0.705(8) 1 calc R U P A 1
N2A N 0.1735(9) 0.6502(4) 0.3311(5) 0.0370(9) Uani 0.705(8) 1 d G U P A 1
C17A C 0.2597(8) 0.7579(3) 0.2634(5) 0.0361(7) Uani 0.705(8) 1 d G U P A 1
H17A H 0.297082 0.860926 0.292299 0.043 Uiso 0.705(8) 1 calc R U P A 1
C18A C 0.2907(7) 0.7133(4) 0.1529(4) 0.0337(7) Uani 0.705(8) 1 d G U P A 1
H18A H 0.348988 0.786119 0.107167 0.04 Uiso 0.705(8) 1 calc R U P A 1
C14B C 0.214(2) 0.5314(14) 0.1163(11) 0.0424(19) Uani 0.295(8) 1 d D U P A 2
C15B C 0.133(2) 0.4507(9) 0.2025(12) 0.0415(18) Uani 0.295(8) 1 d . U P A 2
H15B H 0.086235 0.34478 0.190165 0.05 Uiso 0.295(8) 1 calc R U P A 2
C16B C 0.125(2) 0.5282(13) 0.3042(11) 0.0359(16) Uani 0.295(8) 1 d . U P A 2
H16B H 0.066831 0.465254 0.356533 0.043 Uiso 0.295(8) 1 calc R U P A 2
N2B N 0.175(2) 0.6608(11) 0.3420(12) 0.044(2) Uani 0.295(8) 1 d . U P A 2
C17B C 0.245(2) 0.7267(12) 0.2668(13) 0.0391(17) Uani 0.295(8) 1 d . U P A 2
H17B H 0.293015 0.832438 0.288397 0.047 Uiso 0.295(8) 1 calc R U P A 2
C18B C 0.2714(19) 0.6809(13) 0.1565(13) 0.0431(17) Uani 0.295(8) 1 d . U P A 2
H18B H 0.328077 0.752394 0.109128 0.052 Uiso 0.295(8) 1 calc R U P A 2
C19 C 0.242(3) 0.4033(18) -0.0776(15) 0.045(3) Uani 0.25 1 d D U P A 2
C20 C 0.2445(18) 0.4766(19) 0.0109(10) 0.0516(19) Uani 0.25 1 d D U P A 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
-1 4 4 0.0717
5 4 1 0.0337
-2 -4 3 0.0581
2 5 -2 0.0622
-5 -3 -4 0.0659
-2 -5 2 0.0477
-2 0 5 0.0662
-5 -4 -1 0.0318
-1 -2 -7 0.0688
1 -4 -5 0.0636
-5 0 0 0.0498
2 -4 0 0.0503
3 3 -4 0.0609
0 3 6 0.0788
-2 -6 -1 0.0374
4 0 -2 0.0542
1 -4 3 0.0598
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 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.90(8) . . ?
O1 C1 C2 121.94(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.83(9) . . ?
C1 C2 C3 120.47(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.16(8) . . ?
O2 C3 C4 117.99(9) . . ?
C2 C3 C4 119.85(9) . . ?
C5 C4 C3 118.81(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.92(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.10(9) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.23(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.73(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.9(7) . . ?
C19 C9 C10 114.9(7) . . ?
C8 C9 C10 117.17(9) . . ?
C19 C9 C12B 13.9(8) . . ?
C8 C9 C12B 141.5(10) . . ?
C10 C9 C12B 101.3(10) . . ?
C8 C9 C12A 116.76(17) . . ?
C10 C9 C12A 126.00(17) . . ?
C11 C10 C9 119.11(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.83(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.4(3) . . ?
C13A C12A H12A 118.8 . . ?
C9 C12A H12A 118.8 . . ?
C12A C13A C14A 124.5(3) . . ?
C12A C13A H13A 117.8 . . ?
C14A C13A H13A 117.8 . . ?
C13B C12B C9 142(3) . . ?
C13B C12B H12B 108.8 . . ?
C9 C12B H12B 108.8 . . ?
C12B C13B C14B 145(3) . . ?
C12B C13B H13B 107.5 . . ?
C14B C13B H13B 107.5 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.5(2) . . ?
C18A C14A C13A 117.5(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 123.1(11) . . ?
C18B C14B C15B 108.7(6) . . ?
C20 C14B C15B 128.2(9) . . ?
C18B C14B C13B 137.7(13) . . ?
C20 C14B C13B 14.9(8) . . ?
C15B C14B C13B 113.6(12) . . ?
C16B C15B C14B 118.7(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 133.8(7) . . ?
N2B C16B C17B 37.1(4) . . ?
C15B C16B C17B 96.7(4) . . ?
N2B C16B H16B 113.1 . . ?
C15B C16B H16B 113.1 . . ?
C17B C16B H16B 150.2 . . ?
C17B N2B C16B 105.7(7) . . ?
N2B C17B C18B 133.9(8) . . ?
N2B C17B C16B 37.2(4) . . ?
C18B C17B C16B 96.6(5) . . ?
N2B C17B H17B 113.1 . . ?
C18B C17B H17B 113.1 . . ?
C16B C17B H17B 150.3 . . ?
C14B C18B C17B 119.3(6) . . ?
C14B C18B H18B 120.4 . . ?
C17B C18B H18B 120.4 . . ?
C20 C19 C9 170(2) . . ?
C19 C20 C14B 167(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 1.3574(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3551(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3334(14) . ?
N1 C11 1.3393(14) . ?
C1 C2 1.3871(13) . ?
C1 C6 1.3926(13) . ?
C2 C3 1.3934(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3975(13) . ?
C4 C5 1.3806(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3848(15) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3817(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3886(14) . ?
C8 H8 0.94 . ?
C9 C19 1.372(12) . ?
C9 C10 1.3920(15) . ?
C9 C12B 1.405(19) . ?
C9 C12A 1.499(3) . ?
C10 C11 1.3776(14) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.343(5) . ?
C12A H12A 0.94 . ?
C13A C14A 1.494(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.259(19) . ?
C12B H12B 0.94 . ?
C13B C14B 1.407(18) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.356(9) . ?
C14B C20 1.376(12) . ?
C14B C15B 1.398(9) . ?
C15B C16B 1.355(9) . ?
C15B H15B 0.94 . ?
C16B N2B 1.208(9) . ?
C16B C17B 1.922(15) . ?
C16B H16B 0.94 . ?
N2B C17B 1.203(8) . ?
C17B C18B 1.370(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.169(14) . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.91 2.7425(11) 175.8 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.79(2) 177.3 2_666 yes
O2 H2A N2B^b 0.83 1.82 2.648(9) 177.3 2_666 yes
