#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558204.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_1558204
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 H15.03 N2 O2'
_chemical_formula_weight         291.34
_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             2020-04-01T17:45:00-00:00
_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                92.3839(18)
_cell_angle_beta                 107.8562(13)
_cell_angle_gamma                114.4977(15)
_cell_formula_units_Z            2
_cell_length_a                   8.12328(14)
_cell_length_b                   9.8351(2)
_cell_length_c                   10.91847(14)
_cell_measurement_reflns_used    18862
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      76.705
_cell_measurement_theta_min      4.315
_cell_volume                     741.07(3)
_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      190(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 0.975
_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      -0.0033213
_diffrn_orient_matrix_UB_12      -0.0566512
_diffrn_orient_matrix_UB_13      0.1479079
_diffrn_orient_matrix_UB_21      -0.1506942
_diffrn_orient_matrix_UB_22      0.1531359
_diffrn_orient_matrix_UB_23      0.0272409
_diffrn_orient_matrix_UB_31      -0.1504746
_diffrn_orient_matrix_UB_32      -0.0643381
_diffrn_orient_matrix_UB_33      0.0149157
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_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            28099
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.324
_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    0.697
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.81639
_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    1.306
_exptl_crystal_description       irregular
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0047(7)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     460
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.032
_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)+(0.0444P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.086
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0
_reflns_number_gt                2863
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_190
_cod_original_cell_volume        741.07(2)
_cod_database_code               1558204
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.955
_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 0.16658(9) 0.15097(8) 0.30486(7) 0.03979(18) Uani 1 1 d . . . . .
H1 H 0.2057(8) 0.1817(15) 0.3989(14) 0.06 Uiso 1 1 calc R U . . .
O2 O 0.82157(10) 0.22084(9) 0.43309(7) 0.04583(19) Uani 1 1 d . . . . .
H2A H 0.8271(7) 0.2636(16) 0.5184(14) 0.069 Uiso 1 1 calc R U . . .
N1 N 0.26273(12) 0.24430(10) -0.43203(8) 0.0412(2) Uani 1 1 d . . . . .
C1 C 0.31725(13) 0.14956(9) 0.27605(8) 0.0330(2) Uani 1 1 d . . . . .
C2 C 0.49378(13) 0.18479(9) 0.37361(8) 0.0332(2) Uani 1 1 d . . . . .
H2 H 0.51065 0.209702 0.463047 0.04 Uiso 1 1 calc R U . . .
C3 C 0.64585(14) 0.18372(10) 0.34089(9) 0.0356(2) Uani 1 1 d . . . . .
C4 C 0.62020(15) 0.14405(11) 0.20978(9) 0.0414(2) Uani 1 1 d . . . . .
H4 H 0.722582 0.141423 0.186624 0.05 Uiso 1 1 calc R U . . .
C5 C 0.44318(16) 0.10864(11) 0.11414(9) 0.0444(2) Uani 1 1 d . . . . .
H5 H 0.425367 0.081942 0.024781 0.053 Uiso 1 1 calc R U . . .
C6 C 0.29114(15) 0.11104(11) 0.14507(9) 0.0403(2) Uani 1 1 d . . . . .
H6 H 0.170847 0.08674 0.077853 0.048 Uiso 1 1 calc R U . . .
C7 C 0.19720(14) 0.14668(11) -0.35703(9) 0.0399(2) Uani 1 1 d . . . . .
H7 H 0.154484 0.041401 -0.386674 0.048 Uiso 1 1 calc R U . . .
C8 C 0.18857(14) 0.19132(11) -0.23866(9) 0.0378(2) Uani 1 1 d . . . . .
H8 H 0.13963 0.117626 -0.189051 0.045 Uiso 1 1 calc R U . . .
C9 C 0.25193(13) 0.34483(11) -0.19242(9) 0.0352(2) Uani 1 1 d D U . . .
C10 C 0.32590(14) 0.44748(11) -0.26821(10) 0.0407(2) Uani 1 1 d . . . . .
H10 H 0.375131 0.553846 -0.239197 0.049 Uiso 1 1 calc R U . . .
C11 C 0.32657(15) 0.39233(12) -0.38593(10) 0.0429(2) Uani 1 1 d . . . . .
H11 H 0.375157 0.463439 -0.437526 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2189(10) 0.3794(6) -0.0663(6) 0.0289(8) Uani 0.513(10) 1 d D U P A 1
H12 H 0.162026 0.297113 -0.026265 0.035 Uiso 0.513(10) 1 calc R U P A 1
C13 C 0.2664(4) 0.5190(5) -0.0108(3) 0.0288(6) Uani 0.513(10) 1 d D U P A 1
H13 H 0.327583 0.599737 -0.050843 0.035 Uiso 0.513(10) 1 calc R U P A 1
C14A C 0.2319(11) 0.5619(7) 0.1106(6) 0.0281(10) Uani 0.513(10) 1 d G U P A 1
C15A C 0.1476(12) 0.4533(6) 0.1785(7) 0.0332(11) Uani 0.513(10) 1 d G U P A 1
H15A H 0.110972 0.349016 0.149508 0.04 Uiso 0.513(10) 1 calc R U P A 1
C16A C 0.1169(12) 0.4971(7) 0.2890(7) 0.0344(12) Uani 0.513(10) 1 d G U P A 1
H16A H 0.059292 0.422874 0.335387 0.041 Uiso 0.513(10) 1 calc R U P A 1
N2A N 0.1705(12) 0.6497(8) 0.3314(6) 0.0320(13) Uani 0.513(10) 1 d G U P A 1
C17A C 0.2548(11) 0.7584(6) 0.2635(6) 0.0317(10) Uani 0.513(10) 1 d G U P A 1
H17A H 0.291445 0.862624 0.292516 0.038 Uiso 0.513(10) 1 calc R U P A 1
C18A C 0.2855(11) 0.7145(6) 0.1531(6) 0.0305(10) Uani 0.513(10) 1 d G U P A 1
H18A H 0.343127 0.788769 0.106636 0.037 Uiso 0.513(10) 1 calc R U P A 1
C14B C 0.2162(13) 0.5280(9) 0.1214(7) 0.0358(13) Uani 0.487(10) 1 d . U P A 2
C15B C 0.1284(14) 0.4436(8) 0.2023(8) 0.0405(12) Uani 0.487(10) 1 d . U P A 2
H15B H 0.079037 0.335956 0.187025 0.049 Uiso 0.487(10) 1 calc R U P A 2
C16B C 0.1142(14) 0.5185(9) 0.3045(8) 0.0395(12) Uani 0.487(10) 1 d . U P A 2
H16B H 0.052157 0.456757 0.356934 0.047 Uiso 0.487(10) 1 calc R U P A 2
N2B N 0.1753(14) 0.6630(10) 0.3375(8) 0.0438(16) Uani 0.487(10) 1 d . U P A 2
C17B C 0.2557(14) 0.7380(9) 0.2611(9) 0.0421(13) Uani 0.487(10) 1 d . U P A 2
H17B H 0.304059 0.845412 0.281329 0.051 Uiso 0.487(10) 1 calc R U P A 2
C18B C 0.2807(12) 0.6832(8) 0.1545(7) 0.0362(11) Uani 0.487(10) 1 d . U P A 2
H18B H 0.341143 0.750262 0.104381 0.043 Uiso 0.487(10) 1 calc R U P A 2
C19 C 0.2507(12) 0.4105(9) -0.0794(8) 0.0405(12) Uani 0.487(10) 1 d D U P A 2
C20 C 0.2361(6) 0.4643(7) 0.0145(4) 0.0421(9) Uani 0.487(10) 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
1 0 2 0.1024
2 0 -6 0.081
4 5 0 0.0438
-5 -4 -3 0.0658
-1 4 4 0.0337
-4 -5 0 0.0468
2 6 4 0.0464
5 5 4 0.0804
5 4 -1 0.0444
3 2 -4 0.0582
1 6 -1 0.0561
-1 -6 1 0.0835
-5 -2 0 0.0435
2 -4 2 0.0954
-3 2 1 0.0427
0 6 2 0.0367
2 6 3 0.0426
-2 -6 -3 0.0582
1 2 7 0.0957
4 6 1 0.0435
1 -5 0 0.0733
2 -2 -5 0.054
-4 -6 -4 0.0654
1 -5 -4 0.0508
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 116.96(8) . . ?
O1 C1 C2 121.65(8) . . ?
O1 C1 C6 118.32(8) . . ?
C2 C1 C6 120.03(9) . . ?
C1 C2 C3 120.29(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C2 122.00(8) . . ?
O2 C3 C4 118.02(8) . . ?
C2 C3 C4 119.97(9) . . ?
C5 C4 C3 118.87(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.82(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.18(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.57(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 128.1(3) . . ?
C19 C9 C10 114.5(3) . . ?
C8 C9 C10 117.47(9) . . ?
C8 C9 C12 114.9(2) . . ?
C10 C9 C12 127.5(2) . . ?
C11 C10 C9 118.90(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.87(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.7(5) . . ?
C13 C12 H12 118.6 . . ?
C9 C12 H12 118.6 . . ?
C12 C13 C14A 125.9(5) . . ?
C12 C13 H13 117 . . ?
C14A C13 H13 117 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 121.8(3) . . ?
C18A C14A C13 118.2(3) . . ?
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 121.7(5) . . ?
C18B C14B C15B 114.5(3) . . ?
C20 C14B C15B 123.8(4) . . ?
C16B C15B C14B 118.9(3) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 127.4(4) . . ?
N2B C16B H16B 116.3 . . ?
C15B C16B H16B 116.3 . . ?
C17B N2B C16B 112.3(4) . . ?
N2B C17B C18B 128.4(4) . . ?
N2B C17B H17B 115.8 . . ?
C18B C17B H17B 115.8 . . ?
C17B C18B C14B 118.5(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.4(8) . . ?
C19 C20 C14B 178.6(7) . . ?
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 1.3591(11) . ?
O1 H1 0.970(14) . ?
O2 C3 1.3565(12) . ?
O2 H2A 0.986(15) . ?
N1 C7 1.3358(13) . ?
N1 C11 1.3397(13) . ?
C1 C2 1.3898(13) . ?
C1 C6 1.3914(12) . ?
C2 C3 1.3910(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3958(13) . ?
C4 C5 1.3831(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3854(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3791(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3900(13) . ?
C8 H8 0.95 . ?
C9 C19 1.374(8) . ?
C9 C10 1.3916(14) . ?
C9 C12 1.532(6) . ?
C10 C11 1.3765(14) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.323(7) . ?
C12 H12 0.95 . ?
C13 C14A 1.514(5) . ?
C13 H13 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C18B 1.381(5) . ?
C14B C20 1.386(6) . ?
C14B C15B 1.391(6) . ?
C15B C16B 1.372(5) . ?
C15B H15B 0.95 . ?
C16B N2B 1.287(5) . ?
C16B H16B 0.95 . ?
N2B C17B 1.286(5) . ?
C17B C18B 1.367(4) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.194(8) . ?
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 0.97 1.77 2.7414(10) 175.1 1_556 yes
O2 H2A N2A^a 0.99 1.81 2.79(3) 175.8 2_666 yes
O2 H2A N2B^b 0.99 1.71 2.698(6) 177 2_666 yes
