#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558236.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_1558236
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            'C17.08 H15.08 N2.92 O2'
_chemical_formula_weight         293.24
_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             2020-03-05T13:00:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.323(3)
_cell_angle_beta                 106.8183(17)
_cell_angle_gamma                114.090(2)
_cell_formula_units_Z            2
_cell_length_a                   7.99695(15)
_cell_length_b                   9.8077(3)
_cell_length_c                   10.8728(2)
_cell_measurement_reflns_used    13578
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      76.991
_cell_measurement_theta_min      4.317
_cell_volume                     729.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_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      -0.2095436
_diffrn_orient_matrix_UB_12      0.0769724
_diffrn_orient_matrix_UB_13      0.0525786
_diffrn_orient_matrix_UB_21      0.0348092
_diffrn_orient_matrix_UB_22      -0.0595411
_diffrn_orient_matrix_UB_23      0.1415234
_diffrn_orient_matrix_UB_31      0.0334703
_diffrn_orient_matrix_UB_32      0.1462475
_diffrn_orient_matrix_UB_33      -0.0066256
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23005
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.34
_diffrn_reflns_theta_min         4.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0045(9)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.109
_reflns_Friedel_coverage         0
_reflns_number_gt                2596
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_190
_cod_original_cell_volume        729.91(3)
_cod_database_code               1558236
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.929
_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 0.16455(12) 0.15995(10) 0.30914(8) 0.0415(2) Uani 1 1 d . . . . .
H1 H 0.196636 0.184451 0.390837 0.062 Uiso 1 1 calc R U . . .
O2 O 0.82475(13) 0.22656(11) 0.43342(8) 0.0475(3) Uani 1 1 d . . . . .
H2A H 0.829753 0.266094 0.505843 0.071 Uiso 1 1 calc R U . . .
N1 N 0.26076(15) 0.24851(13) 0.57515(10) 0.0424(3) Uani 1 1 d . . . . .
N2A N 0.219(2) 0.3785(12) 0.9438(11) 0.0362(18) Uani 0.441(3) 1 d D U P A 1
N3A N 0.268(2) 0.5145(12) 0.9837(11) 0.0355(16) Uani 0.441(3) 1 d D U P A 1
C17 C 0.214(2) 0.3773(11) 0.9350(11) 0.0346(15) Uani 0.542(3) 1 d D U P A 2
H17 H 0.154463 0.297118 0.976179 0.042 Uiso 0.542(3) 1 calc DR U P A 2
C18 C 0.2657(18) 0.5191(11) 0.9893(10) 0.0348(15) Uani 0.542(3) 1 d D U P A 2
H18 H 0.32747 0.599406 0.949079 0.042 Uiso 0.542(3) 1 calc R U P A 2
N2B N 0.274(9) 0.465(8) 0.921(6) 0.037(3) Uani 0.0168(18) 1 d D U P A 3
N3B N 0.183(8) 0.407(7) 0.994(6) 0.037(3) Uani 0.0168(18) 1 d D U P A 3
N4 N 0.17514(14) 0.65071(12) 1.33044(9) 0.0403(2) Uani 1 1 d . . . . .
C1 C 0.31635(17) 0.15568(12) 0.27958(11) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.49414(17) 0.19199(12) 0.37611(10) 0.0345(3) Uani 1 1 d . . . . .
H2 H 0.511165 0.219525 0.465674 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64765(17) 0.18821(13) 0.34218(11) 0.0365(3) Uani 1 1 d . . . . .
C4 C 0.62185(19) 0.14474(14) 0.21100(12) 0.0413(3) Uani 1 1 d . . . . .
H4 H 0.724838 0.139891 0.187098 0.05 Uiso 1 1 calc R U . . .
C5 C 0.4439(2) 0.10886(14) 0.11645(11) 0.0429(3) Uani 1 1 d . . . . .
H5 H 0.426269 0.080275 0.026945 0.052 Uiso 1 1 calc R U . . .
C6 C 0.29027(19) 0.11335(14) 0.14833(11) 0.0405(3) Uani 1 1 d . . . . .
H6 H 0.169015 0.087953 0.081699 0.049 Uiso 1 1 calc R U . . .
C7 C 0.32306(18) 0.39591(15) 0.62511(12) 0.0430(3) Uani 1 1 d . . . . .
H7 H 0.373062 0.469156 0.575481 0.052 Uiso 1 1 calc R U . . .
C8 C 0.31875(18) 0.44734(14) 0.74441(12) 0.0405(3) Uani 1 1 d . . . . .
H8 H 0.366204 0.553192 0.776303 0.049 Uiso 1 1 calc R U . . .
C9 C 0.24333(16) 0.34071(13) 0.81706(11) 0.0346(3) Uani 1 1 d D . . . .
C10 C 0.18208(18) 0.18808(14) 0.76742(12) 0.0400(3) Uani 1 1 d . . . . .
H10 H 0.132452 0.112371 0.815216 0.048 Uiso 1 1 calc R U . . .
C11 C 0.19422(18) 0.14772(15) 0.64758(12) 0.0419(3) Uani 1 1 d . . . . .
H11 H 0.153192 0.043042 0.615075 0.05 Uiso 1 1 calc R U . . .
C12 C 0.23269(16) 0.55575(14) 1.10532(11) 0.0349(3) Uani 1 1 d D . . . .
C13 C 0.28728(18) 0.70797(14) 1.14973(12) 0.0414(3) Uani 1 1 d . . . . .
H13 H 0.345256 0.782757 1.103701 0.05 Uiso 1 1 calc R U . . .
C14 C 0.25663(19) 0.75013(14) 1.26170(12) 0.0434(3) Uani 1 1 d . . . . .
H14 H 0.295496 0.855117 1.291208 0.052 Uiso 1 1 calc R U . . .
C15 C 0.12140(18) 0.50329(14) 1.28702(11) 0.0398(3) Uani 1 1 d . . . . .
H15 H 0.062469 0.431015 1.334558 0.048 Uiso 1 1 calc R U . . .
C16 C 0.14749(17) 0.45100(14) 1.17619(12) 0.0387(3) Uani 1 1 d . . . . .
H16 H 0.107904 0.345419 1.149029 0.046 Uiso 1 1 calc DR 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 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
4 6 1 0.0681
0 6 2 0.0494
-4 -5 -1 0.0905
0 -6 -2 0.0863
3 -3 -2 0.1171
1 1 7 0.036
1 3 -4 0.0457
-2 -4 -7 0.0731
-3 -6 -3 0.0873
2 1 -5 0.0681
0 -3 -6 0.0553
-3 -2 4 0.092
3 -3 2 0.1189
-4 1 -3 0.1384
-1 3 -5 0.0535
0 0 -7 0.0505
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 . . ?
C11 N1 C7 117.11(10) . . ?
N3A N2A C9 116.3(9) . . ?
N2A N3A C12 118.0(10) . . ?
C18 C17 C9 122.2(9) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 122.4(9) . . ?
C17 C18 H18 118.8 . . ?
C12 C18 H18 118.8 . . ?
N3B N2B C9 109(6) . . ?
N2B N3B C12 104(6) . . ?
C14 N4 C15 117.34(10) . . ?
O1 C1 C2 121.80(10) . . ?
O1 C1 C6 118.25(10) . . ?
C2 C1 C6 119.94(11) . . ?
C1 C2 C3 120.30(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.95(10) . . ?
O2 C3 C4 118.06(11) . . ?
C2 C3 C4 119.99(11) . . ?
C5 C4 C3 118.82(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.99(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.79(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.53(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.11(11) . . ?
C10 C9 C17 117.8(4) . . ?
C8 C9 C17 124.0(4) . . ?
C10 C9 N2A 117.4(4) . . ?
C8 C9 N2A 124.5(4) . . ?
C10 C9 N2B 151(2) . . ?
C8 C9 N2B 91(2) . . ?
C11 C10 C9 119.13(11) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.29(11) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 117.89(11) . . ?
C13 C12 C18 116.8(4) . . ?
C16 C12 C18 125.3(4) . . ?
C13 C12 N3A 117.8(4) . . ?
C16 C12 N3A 124.3(4) . . ?
C13 C12 N3B 154.0(18) . . ?
C16 C12 N3B 87.4(18) . . ?
C14 C13 C12 119.34(12) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.28(12) . . ?
N4 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N4 C15 C16 123.25(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.89(11) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?
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 1.3581(14) . ?
O1 H1 0.84 . ?
O2 C3 1.3566(14) . ?
O2 H2A 0.84 . ?
N1 C11 1.3356(17) . ?
N1 C7 1.3408(16) . ?
N2A N3A 1.237(7) . ?
N2A C9 1.493(10) . ?
N3A C12 1.494(10) . ?
C17 C18 1.321(7) . ?
C17 C9 1.422(10) . ?
C17 H17 0.95 . ?
C18 C12 1.417(10) . ?
C18 H18 0.95 . ?
N2B N3B 1.240(10) . ?
N2B C9 1.50(7) . ?
N3B C12 1.68(7) . ?
N4 C14 1.3349(17) . ?
N4 C15 1.3395(16) . ?
C1 C2 1.3891(16) . ?
C1 C6 1.3931(16) . ?
C2 C3 1.3936(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3950(16) . ?
C4 C5 1.3818(18) . ?
C4 H4 0.95 . ?
C5 C6 1.3853(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3793(17) . ?
C7 H7 0.95 . ?
C8 C9 1.3921(18) . ?
C8 H8 0.95 . ?
C9 C10 1.3881(16) . ?
C10 C11 1.3815(17) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3839(17) . ?
C12 C16 1.3919(17) . ?
C13 C14 1.3821(18) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3856(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
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 0.84 1.92 2.7544(13) 176.2 . yes
O2 H2A N4 0.84 1.93 2.7713(13) 176.6 2_667 yes
