#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558240.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_1558240
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            'C17.05 H15.05 N2.95 O2'
_chemical_formula_weight         293.27
_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             2020-03-05T13:03:51-00:00
_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                93.7995(18)
_cell_angle_beta                 106.674(2)
_cell_angle_gamma                113.898(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0886(2)
_cell_length_b                   9.8583(2)
_cell_length_c                   10.9012(2)
_cell_measurement_reflns_used    9600
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      74.962
_cell_measurement_theta_min      4.296
_cell_volume                     744.61(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      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.949
_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      0.132173
_diffrn_orient_matrix_UB_12      -0.0749023
_diffrn_orient_matrix_UB_13      0.0543468
_diffrn_orient_matrix_UB_21      0.0198791
_diffrn_orient_matrix_UB_22      0.0590621
_diffrn_orient_matrix_UB_23      0.1404352
_diffrn_orient_matrix_UB_31      -0.1770728
_diffrn_orient_matrix_UB_32      -0.146433
_diffrn_orient_matrix_UB_33      -0.0086657
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25036
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.177
_diffrn_reflns_theta_min         4.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.495
_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    1.308
_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         0.195
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0052(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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0415
_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)+(0.0598P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0
_reflns_number_gt                2311
_reflns_number_total             3000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_290
_cod_database_code               1558240
_shelx_estimated_absorpt_t_min   0.87
_shelx_estimated_absorpt_t_max   0.93
_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 0.16665(16) 0.15562(14) 0.30938(10) 0.0669(3) Uani 1 1 d . . . . .
H1 H 0.19745 0.179655 0.389005 0.1 Uiso 1 1 calc R U . . .
O2 O 0.81952(17) 0.22494(16) 0.43217(11) 0.0774(4) Uani 1 1 d . . . . .
H2A H 0.823315 0.261231 0.503389 0.116 Uiso 1 1 calc R U . . .
N1 N 0.2599(2) 0.24740(17) 0.57523(13) 0.0652(4) Uani 1 1 d . . . . .
N2A N 0.226(3) 0.3797(19) 0.9437(15) 0.054(2) Uani 0.370(3) 1 d D U P A 1
N3A N 0.270(3) 0.512(2) 0.9887(17) 0.056(2) Uani 0.370(3) 1 d D U P A 1
C17 C 0.210(3) 0.3775(16) 0.9350(12) 0.0533(17) Uani 0.525(3) 1 d D U P A 2
H17 H 0.152388 0.300227 0.975383 0.064 Uiso 0.525(3) 1 calc DR U P A 2
C18 C 0.262(3) 0.5187(17) 0.9841(14) 0.0529(14) Uani 0.525(3) 1 d D U P A 2
H18 H 0.316118 0.59565 0.942571 0.064 Uiso 0.525(3) 1 calc R U P A 2
N2B N 0.275(2) 0.4694(19) 0.9244(13) 0.057(2) Uani 0.106(2) 1 d D U P A 3
N3B N 0.1921(19) 0.4055(16) 0.9984(13) 0.055(2) Uani 0.106(2) 1 d D U P A 3
N4 N 0.17733(18) 0.65036(16) 1.33035(12) 0.0614(3) Uani 1 1 d . . . . .
C1 C 0.3175(2) 0.15223(16) 0.27975(14) 0.0529(3) Uani 1 1 d . . . . .
C2 C 0.4927(2) 0.18871(16) 0.37545(13) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.508885 0.21487 0.463097 0.065 Uiso 1 1 calc R U . . .
C3 C 0.6446(2) 0.18650(17) 0.34141(14) 0.0573(4) Uani 1 1 d . . . . .
C4 C 0.6192(3) 0.14410(19) 0.21071(16) 0.0649(4) Uani 1 1 d . . . . .
H4 H 0.719036 0.14015 0.186944 0.078 Uiso 1 1 calc R U . . .
C5 C 0.4439(3) 0.10806(19) 0.11707(15) 0.0678(5) Uani 1 1 d . . . . .
H5 H 0.427057 0.080645 0.029467 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2924(3) 0.11134(18) 0.14912(15) 0.0628(4) Uani 1 1 d . . . . .
H6 H 0.175177 0.086488 0.084097 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3221(2) 0.3943(2) 0.62403(17) 0.0673(4) Uani 1 1 d . . . . .
H7 H 0.369963 0.464431 0.574963 0.081 Uiso 1 1 calc R U . . .
C8 C 0.3190(2) 0.4473(2) 0.74307(16) 0.0649(4) Uani 1 1 d . . . . .
H8 H 0.365928 0.550775 0.773987 0.078 Uiso 1 1 calc R U . . .
C9 C 0.2449(2) 0.34386(19) 0.81569(14) 0.0567(4) Uani 1 1 d D . . . .
C10 C 0.1841(2) 0.19290(19) 0.76702(16) 0.0640(4) Uani 1 1 d . . . . .
H10 H 0.136219 0.120377 0.814242 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1946(2) 0.1502(2) 0.64847(16) 0.0657(4) Uani 1 1 d . . . . .
H11 H 0.153745 0.047723 0.617469 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2312(2) 0.5528(2) 1.10606(14) 0.0584(4) Uani 1 1 d D . . . .
C13 C 0.2850(3) 0.7023(2) 1.14968(16) 0.0673(4) Uani 1 1 d . . . . .
H13 H 0.340231 0.774166 1.104161 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2573(3) 0.7459(2) 1.26087(17) 0.0685(4) Uani 1 1 d . . . . .
H14 H 0.296753 0.848717 1.289511 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1229(2) 0.5038(2) 1.28790(15) 0.0625(4) Uani 1 1 d . . . . .
H15 H 0.065774 0.434589 1.33468 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1476(2) 0.44986(19) 1.17684(16) 0.0636(4) Uani 1 1 d . . . . .
H16 H 0.108874 0.346817 1.150359 0.076 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 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -5 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 3 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171
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 116.76(14) . . ?
N3A N2A C9 118.4(13) . . ?
N2A N3A C12 121.1(14) . . ?
C18 C17 C9 118.3(11) . . ?
C18 C17 H17 120.8 . . ?
C9 C17 H17 120.8 . . ?
C17 C18 C12 118.3(12) . . ?
C17 C18 H18 120.9 . . ?
C12 C18 H18 120.9 . . ?
N3B N2B C9 107.2(15) . . ?
N2B N3B C12 101.7(13) . . ?
C14 N4 C15 116.99(14) . . ?
O1 C1 C2 122.00(12) . . ?
O1 C1 C6 118.17(14) . . ?
C2 C1 C6 119.84(14) . . ?
C1 C2 C3 120.42(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.06(13) . . ?
O2 C3 C4 118.12(14) . . ?
C2 C3 C4 119.82(15) . . ?
C5 C4 C3 118.87(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(14) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.03(15) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.51(16) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.71(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 117.96(14) . . ?
C10 C9 C17 115.7(6) . . ?
C8 C9 C17 126.1(6) . . ?
C10 C9 N2A 115.9(7) . . ?
C8 C9 N2A 126.2(7) . . ?
C10 C9 N2B 149.5(5) . . ?
C8 C9 N2B 92.5(5) . . ?
C11 C10 C9 119.45(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.56(16) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C13 C12 C16 117.96(15) . . ?
C13 C12 C18 114.8(6) . . ?
C16 C12 C18 127.2(7) . . ?
C13 C12 N3A 117.5(7) . . ?
C16 C12 N3A 124.5(7) . . ?
C13 C12 N3B 154.0(4) . . ?
C16 C12 N3B 87.8(4) . . ?
C12 C13 C14 119.51(16) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N4 C14 C13 123.92(16) . . ?
N4 C14 H14 118 . . ?
C13 C14 H14 118 . . ?
N4 C15 C16 122.87(16) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.72(16) . . ?
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 1.3606(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3554(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.330(2) . ?
N1 C7 1.337(2) . ?
N2A N3A 1.228(8) . ?
N2A C9 1.483(13) . ?
N3A C12 1.471(14) . ?
C17 C18 1.304(7) . ?
C17 C9 1.453(11) . ?
C17 H17 0.93 . ?
C18 C12 1.461(11) . ?
C18 H18 0.93 . ?
N2B N3B 1.237(10) . ?
N2B C9 1.547(16) . ?
N3B C12 1.665(15) . ?
N4 C14 1.327(2) . ?
N4 C15 1.332(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.387(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.93 . ?
C3 C4 1.389(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.93 . ?
C5 C6 1.379(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.377(2) . ?
C7 H7 0.93 . ?
C8 C9 1.382(2) . ?
C8 H8 0.93 . ?
C9 C10 1.375(2) . ?
C10 C11 1.369(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.363(2) . ?
C12 C16 1.389(2) . ?
C13 C14 1.367(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.389(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
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 0.82 1.94 2.7625(17) 175.3 . yes
O2 H2A N4 0.82 1.96 2.7801(16) 177.5 2_667 yes
